//
//  Copyright (C) 2003-2018 Greg Landrum and Rational Discovery LLC
//
//   @@ All Rights Reserved @@
//  This file is part of the RDKit.
//  The contents are covered by the terms of the BSD license
//  which is included in the file license.txt, found at the root
//  of the RDKit source tree.
//

#include <RDGeneral/test.h>
#include <GraphMol/RDKitBase.h>
#include <GraphMol/SmilesParse/SmilesParse.h>
#include <GraphMol/SmilesParse/SmilesWrite.h>
#include <GraphMol/SmilesParse/SmartsWrite.h>
#include <GraphMol/FileParsers/FileParsers.h>
#include <GraphMol/FileParsers/MolSupplier.h>
#include <GraphMol/Fingerprints/Fingerprints.h>
#include <GraphMol/Fingerprints/MorganFingerprints.h>
#include <GraphMol/Fingerprints/MACCS.h>
#include <GraphMol/Fingerprints/AtomPairs.h>
#include <GraphMol/Substruct/SubstructMatch.h>
#include <DataStructs/ExplicitBitVect.h>
#include <DataStructs/BitOps.h>
#include <RDGeneral/RDLog.h>
#include <string>
#include <boost/version.hpp>

using namespace RDKit;

void test1() {
  BOOST_LOG(rdInfoLog) << "testing basics" << std::endl;
  {
    std::string smi = "C1=CC=CC=C1";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1->getNumAtoms() == 6);
    ExplicitBitVect *fp1 = RDKFingerprintMol(*m1);
    ExplicitBitVect *fp2 = RDKFingerprintMol(*m1);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) == 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) >= 0.0);

    smi = "C1=CC=CC=N1";
    RWMol *m2 = SmilesToMol(smi);
    delete fp2;
    fp2 = RDKFingerprintMol(*m2);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) > 0.0);

    delete m1;
    delete m2;
    delete fp1;
    delete fp2;
  }

  {
    std::string smi = "Cc1ccc(C(F)(F)F)o1";
    RWMol *m1 = SmilesToMol(smi);
    std::vector<std::uint32_t> vs1(m1->getNumAtoms());
    for (unsigned int i = 0; i < m1->getNumAtoms(); ++i) {
      vs1[i] = m1->getAtomWithIdx(i)->getAtomicNum();
    }
    std::cerr << "\n\n\n\n\n\n\n\n\n-------------------" << std::endl;
    ExplicitBitVect *fp1 =
        RDKFingerprintMol(*m1, 1, 5, 1024, 1, 0, -1, 0, 1, 1, &vs1);
    smi = "c1ccoc1";
    RWMol *m2 = SmilesToMol(smi);
    std::vector<std::uint32_t> vs2(m2->getNumAtoms());
    for (unsigned int i = 0; i < m2->getNumAtoms(); ++i) {
      vs2[i] = m2->getAtomWithIdx(i)->getAtomicNum();
    }
    std::cerr << "\n\n\n\n\n\n\n\n\n-------------------" << std::endl;
    ExplicitBitVect *fp2 =
        RDKFingerprintMol(*m2, 1, 5, 1024, 1, 0, -1, 0, 1, 1, &vs2);

    TEST_ASSERT(((*fp1) & (*fp2)) == (*fp2));
    delete m1;
    delete m2;
    delete fp1;
    delete fp2;
  }

  {
    std::string smi = "Oc1cc2[nH]cnc2c(O)n1";
    RWMol *m1 = SmilesToMol(smi);
    std::vector<std::uint32_t> vs1(m1->getNumAtoms());
    for (unsigned int i = 0; i < m1->getNumAtoms(); ++i) {
      vs1[i] = m1->getAtomWithIdx(i)->getAtomicNum();
    }
    m1->debugMol(std::cerr);
    std::cerr << "\n\n\n\n\n\n\n\n\n-------------------" << std::endl;
    ExplicitBitVect *fp1 =
        RDKFingerprintMol(*m1, 4, 4, 1024, 1, 0, -1, 0, 1, 1, &vs1);

    for (unsigned int i = 0; i < m1->getNumAtoms(); ++i) {
      smi = MolToSmiles(*m1, false, false, i, false);
      RWMol *m2 = SmilesToMol(smi);
      std::vector<std::uint32_t> vs2(m2->getNumAtoms());
      for (unsigned int i = 0; i < m2->getNumAtoms(); ++i) {
        vs2[i] = m2->getAtomWithIdx(i)->getAtomicNum();
      }
      std::cerr << "SMI: " << smi << std::endl;
      m2->debugMol(std::cerr);
      std::cerr << "\n\n\n\n\n\n\n\n\n-------------------" << std::endl;
      ExplicitBitVect *fp2 =
          RDKFingerprintMol(*m2, 4, 4, 1024, 1, 0, -1, 0, 1, 1, &vs2);
      IntVect iv;
      ((*fp2) ^ (*fp1)).getOnBits(iv);
      std::copy(iv.begin(), iv.end(),
                std::ostream_iterator<int>(std::cerr, ", "));
      std::cerr << std::endl;

      TEST_ASSERT((*fp1) == (*fp2));
      delete m2;
      delete fp2;
    }
    delete m1;
    delete fp1;
  }
  {
    std::string smi = "Oc1cc2[nH]cnc2c(O)n1";
    RWMol *m1 = SmilesToMol(smi);
    std::vector<std::uint32_t> vs1(m1->getNumAtoms());
    for (unsigned int i = 0; i < m1->getNumAtoms(); ++i) {
      vs1[i] = m1->getAtomWithIdx(i)->getAtomicNum();
    }
    std::cerr << "\n\n\n\n\n\n\n\n\n-------------------" << std::endl;
    ExplicitBitVect *fp1 =
        RDKFingerprintMol(*m1, 1, 5, 1024, 1, 0, -1, 0, 1, 1, &vs1);
    smi = "c1ccncc1";
    RWMol *m2 = SmilesToMol(smi);
    std::vector<std::uint32_t> vs2(m2->getNumAtoms());
    for (unsigned int i = 0; i < m2->getNumAtoms(); ++i) {
      vs2[i] = m2->getAtomWithIdx(i)->getAtomicNum();
    }
    std::cerr << "\n\n\n\n\n\n\n\n\n-------------------" << std::endl;
    ExplicitBitVect *fp2 =
        RDKFingerprintMol(*m2, 1, 5, 1024, 1, 0, -1, 0, 1, 1, &vs2);

    IntVect iv;
    ((*fp2) ^ ((*fp1) & (*fp2))).getOnBits(iv);
    std::copy(iv.begin(), iv.end(),
              std::ostream_iterator<int>(std::cerr, ", "));
    std::cerr << std::endl;

    TEST_ASSERT(((*fp1) & (*fp2)) == (*fp2));
    delete m1;
    delete m2;
    delete fp1;
    delete fp2;
  }

  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}
void test2() {
  BOOST_LOG(rdInfoLog) << "testing subgraph invariants" << std::endl;

  std::string smi = "CC(=O)COC";
  RWMol *m1 = SmilesToMol(smi);
  TEST_ASSERT(m1->getNumAtoms() == 6);
  BOOST_LOG(rdInfoLog) << "--------------------  fp1 " << std::endl;
  ExplicitBitVect *fp1 = RDKFingerprintMol(*m1, 1, 4, 2048, 4, false);
  BOOST_LOG(rdInfoLog) << "--------------------  fp2 " << std::endl;
  ExplicitBitVect *fp2 = RDKFingerprintMol(*m1, 1, 4, 2048, 4, false);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) == 1.0);

  RWMol *m2 = SmilesToMol("CC");
  delete fp2;
  BOOST_LOG(rdInfoLog) << "--------------------  fp2 " << std::endl;
  fp2 = RDKFingerprintMol(*m2, 1, 4, 2048, 4, false);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) < 1.0);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) > 0.0);
  TEST_ASSERT(OnBitProjSimilarity(*fp2, *fp1)[0] == 1.0);

  delete m2;
  m2 = SmilesToMol("CC=O");
  delete fp2;
  fp2 = RDKFingerprintMol(*m2, 1, 4, 2048, 4, false);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) < 1.0);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) > 0.0);
  TEST_ASSERT(OnBitProjSimilarity(*fp2, *fp1)[0] == 1.0);

  delete m2;
  m2 = SmilesToMol("CCCOC");
  delete fp2;
  fp2 = RDKFingerprintMol(*m2, 1, 4, 2048, 4, false);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) < 1.0);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) > 0.0);
  TEST_ASSERT(OnBitProjSimilarity(*fp2, *fp1)[0] == 1.0);

  delete m1;
  delete m2;
  delete fp1;
  delete fp2;

  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void test3() {
  BOOST_LOG(rdInfoLog) << "testing auto folding" << std::endl;

  RWMol *m = SmilesToMol("CCCOC");

  ExplicitBitVect *fp1, *fp2;
  fp2 = RDKFingerprintMol(*m, 1, 4, 2048, 4, false, 0.3, 256);
  TEST_ASSERT(fp2->getNumBits() == 256);

  delete m;
  delete fp2;
  m = SmilesToMol("CN(C)Cc1n-2c(nn1)CN=C(c1ccccc1)c1cc(Cl)ccc12");
  fp1 = RDKFingerprintMol(*m, 1, 4, 2048, 4, false);
  TEST_ASSERT(fp1->getNumBits() == 2048);
  fp2 = RDKFingerprintMol(*m, 1, 4, 2048, 4, false, 0.3, 256);
  TEST_ASSERT(fp2->getNumBits() < fp1->getNumBits());

  delete m;
  delete fp1;
  delete fp2;
  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void test1alg2() {
  BOOST_LOG(rdInfoLog) << "testing basics alg2" << std::endl;

  std::string smi = "C1=CC=CC=C1";
  RWMol *m1 = SmilesToMol(smi);
  TEST_ASSERT(m1->getNumAtoms() == 6);
  ExplicitBitVect *fp1 = RDKFingerprintMol(*m1);
  ExplicitBitVect *fp2 = RDKFingerprintMol(*m1);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) == 1.0);

  smi = "C1=CC=CC=N1";
  RWMol *m2 = SmilesToMol(smi);
  delete fp2;
  fp2 = RDKFingerprintMol(*m2);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) < 1.0);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) > 0.0);

  delete m1;
  delete m2;
  delete fp1;
  delete fp2;
  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void test2alg2() {
  BOOST_LOG(rdInfoLog) << "testing subgraph invariants alg2" << std::endl;

  std::string smi = "CC(=O)COC";
  RWMol *m1 = SmilesToMol(smi);
  TEST_ASSERT(m1->getNumAtoms() == 6);
  BOOST_LOG(rdInfoLog) << "--------------------  fp1 " << std::endl;
  ExplicitBitVect *fp1 = RDKFingerprintMol(*m1, 1, 4, 2048, 4, false);
  BOOST_LOG(rdInfoLog) << "--------------------  fp2 " << std::endl;
  ExplicitBitVect *fp2 = RDKFingerprintMol(*m1, 1, 4, 2048, 4, false);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) == 1.0);

  RWMol *m2 = SmilesToMol("CC");
  delete fp2;
  BOOST_LOG(rdInfoLog) << "--------------------  fp2 " << std::endl;
  fp2 = RDKFingerprintMol(*m2, 1, 4, 2048, 4, false);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) < 1.0);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) > 0.0);
  TEST_ASSERT(OnBitProjSimilarity(*fp2, *fp1)[0] == 1.0);

  delete m2;
  m2 = SmilesToMol("CC=O");
  delete fp2;
  fp2 = RDKFingerprintMol(*m2, 1, 4, 2048, 4, false);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) < 1.0);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) > 0.0);
  TEST_ASSERT(OnBitProjSimilarity(*fp2, *fp1)[0] == 1.0);

  delete m2;
  m2 = SmilesToMol("CCCOC");
  delete fp2;
  fp2 = RDKFingerprintMol(*m2, 1, 4, 2048, 4, false);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) < 1.0);
  TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) > 0.0);
  TEST_ASSERT(OnBitProjSimilarity(*fp2, *fp1)[0] == 1.0);

  delete m1;
  delete m2;
  delete fp1;
  delete fp2;

  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void test4Trends() {
  BOOST_LOG(rdInfoLog) << "testing similarity trends" << std::endl;

  double sim1, sim2;
  RWMol *m;
  ExplicitBitVect *fp1, *fp2;

  m = SmilesToMol("CCC");
  fp1 = RDKFingerprintMol(*m);
  delete m;
  m = SmilesToMol("C1CC1");
  fp2 = RDKFingerprintMol(*m);
  sim1 = TanimotoSimilarity(*fp1, *fp2);

  delete m;
  m = SmilesToMol("CCCC");
  delete fp1;
  fp1 = RDKFingerprintMol(*m);
  delete m;
  m = SmilesToMol("C1CCC1");
  delete fp2;
  fp2 = RDKFingerprintMol(*m);
  sim2 = TanimotoSimilarity(*fp1, *fp2);
  TEST_ASSERT(sim2 > sim1);
  sim2 = sim1;

  delete m;
  m = SmilesToMol("CCCCC");
  delete fp1;
  fp1 = RDKFingerprintMol(*m);
  delete m;
  m = SmilesToMol("C1CCCC1");
  delete fp2;
  fp2 = RDKFingerprintMol(*m);
  sim2 = TanimotoSimilarity(*fp1, *fp2);
  TEST_ASSERT(sim2 > sim1);
  sim2 = sim1;

  delete m;
  m = SmilesToMol("CCCCCC");
  delete fp1;
  fp1 = RDKFingerprintMol(*m);
  delete m;
  m = SmilesToMol("C1CCCCC1");
  delete fp2;
  fp2 = RDKFingerprintMol(*m);
  sim2 = TanimotoSimilarity(*fp1, *fp2);
  TEST_ASSERT(sim2 > sim1);
  sim2 = sim1;

  delete m;
  m = SmilesToMol("CCCCCCC");
  delete fp1;
  fp1 = RDKFingerprintMol(*m);
  delete m;
  m = SmilesToMol("C1CCCCCC1");
  delete fp2;
  fp2 = RDKFingerprintMol(*m);
  sim2 = TanimotoSimilarity(*fp1, *fp2);
  TEST_ASSERT(sim2 > sim1);
  sim2 = sim1;

  delete m;
  delete fp1;
  delete fp2;

  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void test5BackwardsCompatibility() {
  BOOST_LOG(rdInfoLog) << "testing backwards compatibility of fingerprints"
                       << std::endl;

  RWMol *m;
  ExplicitBitVect *fp1;

  m = SmilesToMol("CC");
  fp1 = RDKFingerprintMol(*m, 1, 7, 2048, 4);
  TEST_ASSERT(fp1->getNumOnBits() == 4);
#if BOOST_VERSION / 100 < 1040
  // bug fixes in the uniform_int<> distribution in version 1.40
  // necessitate this
  TEST_ASSERT((*fp1)[951]);
  TEST_ASSERT((*fp1)[961]);
  TEST_ASSERT((*fp1)[1436]);
  TEST_ASSERT((*fp1)[1590]);
#else
  TEST_ASSERT((*fp1)[419]);
  TEST_ASSERT((*fp1)[718]);
  TEST_ASSERT((*fp1)[1499]);
  TEST_ASSERT((*fp1)[1504]);
#endif
  delete fp1;

  delete m;

  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void test1Layers() {
  BOOST_LOG(rdInfoLog) << "testing basics layered fps" << std::endl;
#if 1
  {
    RWMol *m1 = SmilesToMol("C1=CC=CC=C1");
    RWMol *m2 = SmilesToMol("C1=CC=CC=N1");
    RWMol *m3 = SmilesToMol("C1CCCCC1");
    RWMol *m4 = SmilesToMol("C1CCC1");

    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1);
    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m1);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) == 1.0);

    delete fp2;
    fp2 = LayeredFingerprintMol(*m2);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) > 0.0);

    ExplicitBitVect *fp3 = LayeredFingerprintMol(*m3);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp3) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp3) > 0.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp3) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp3) > 0.0);

    ExplicitBitVect *fp4 = LayeredFingerprintMol(*m4);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp4) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp4) > 0.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp4) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp4) > 0.0);
    TEST_ASSERT(TanimotoSimilarity(*fp3, *fp4) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp3, *fp4) > 0.0);

    delete fp1;
    delete fp2;
    delete fp3;
    delete fp4;
    delete m1;
    delete m2;
    delete m3;
    delete m4;
  }
#endif
  {
    RWMol *m1 = SmilesToMol("C1=CC=CC=C1");
    RWMol *m2 = SmilesToMol("C1=CC=CC=N1");
    RWMol *m3 = SmilesToMol("C1CCCCC1");
    RWMol *m4 = SmilesToMol("CCCCCC");
    unsigned int layers = 0x1;
    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, layers, 1, 5);

    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) == 1.0);

    ExplicitBitVect *fp3 = LayeredFingerprintMol(*m3, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp3) == 1.0);

    ExplicitBitVect *fp4 = LayeredFingerprintMol(*m4, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp4) == 1.0);

    delete fp1;
    delete fp2;
    delete fp3;
    delete fp4;
    delete m1;
    delete m2;
    delete m3;
    delete m4;
  }

  {
    RWMol *m1 = SmilesToMol("C1=CC=CC=C1");
    RWMol *m2 = SmilesToMol("C1=CC=CC=N1");
    RWMol *m3 = SmilesToMol("C1CCCCC1");
    RWMol *m4 = SmilesToMol("CCCCCC");
    unsigned int layers = 0x3;
    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, layers, 1, 5);

    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) == 1.0);

    ExplicitBitVect *fp3 = LayeredFingerprintMol(*m3, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp3) == 1.0);

    ExplicitBitVect *fp4 = LayeredFingerprintMol(*m4, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp4) <= 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp4) > 0.0);
    TEST_ASSERT(TanimotoSimilarity(*fp3, *fp4) == 1.0);

    delete fp1;
    delete fp2;
    delete fp3;
    delete fp4;
    delete m1;
    delete m2;
    delete m3;
    delete m4;
  }

  {
    RWMol *m1 = SmilesToMol("C1=CC=CC=C1");
    RWMol *m2 = SmilesToMol("C1=CC=CC=N1");
    RWMol *m3 = SmilesToMol("C1CCCCC1");
    RWMol *m4 = SmilesToMol("CCCCCC");
    unsigned int layers = 0x7;
    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, layers, 1, 5);

    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) > 0.0);

    ExplicitBitVect *fp3 = LayeredFingerprintMol(*m3, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp3) == 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp3) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp3) > 0.0);

    ExplicitBitVect *fp4 = LayeredFingerprintMol(*m4, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp4) == 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp4) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp4) > 0.0);
    TEST_ASSERT(TanimotoSimilarity(*fp3, *fp4) == 1.0);

    delete fp1;
    delete fp2;
    delete fp3;
    delete fp4;
    delete m1;
    delete m2;
    delete m3;
    delete m4;
  }

  {
    RWMol *m1 = SmilesToMol("c1ccccc1");
    RWMol *m2 = SmilesToMol("C1CCCCC1");
    RWMol *m3 = SmilesToMol("CCCCCC");
    RWMol *m4 = SmilesToMol("C1CCCCC1");
    unsigned int layers = 0xF;  // add the "in ring" bit
    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, layers, 1, 5);

    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) == 1.0);

    ExplicitBitVect *fp3 = LayeredFingerprintMol(*m3, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp3) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp3) > 0.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp3) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp3) > 0.0);

    ExplicitBitVect *fp4 = LayeredFingerprintMol(*m4, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp4) == 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp4) == 1.0);

    delete fp1;
    delete fp2;
    delete fp3;
    delete fp4;
    delete m1;
    delete m2;
    delete m3;
    delete m4;
  }

  {
    RWMol *m1 = SmilesToMol("C1=CC=CC=C1");
    RWMol *m2 = SmilesToMol("C1CCCCC1");
    RWMol *m3 = SmilesToMol("CCCCCC");
    RWMol *m4 = SmilesToMol("C1CCCCCC1");
    unsigned int layers = 0x1F;  // add the ring size bit
    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, layers, 1, 5);

    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) == 1.0);

    ExplicitBitVect *fp3 = LayeredFingerprintMol(*m3, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp3) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp3) > 0.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp3) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp3) > 0.0);

    ExplicitBitVect *fp4 = LayeredFingerprintMol(*m4, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp4) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp4) > 0.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp4) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp2, *fp4) > 0.0);
    TEST_ASSERT(TanimotoSimilarity(*fp3, *fp4) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp3, *fp4) > 0.0);

    delete fp1;
    delete fp2;
    delete fp3;
    delete fp4;
    delete m1;
    delete m2;
    delete m3;
    delete m4;
  }

  {
    RWMol *m1 = SmilesToMol("Cc1ncccc1");
    RWMol *m2 = SmilesToMol("Cn1ccc2nn(C)c(=O)c-2c1C");
    unsigned int layers = 0x7;
    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, layers, 1, 5);

    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, layers, 1, 5);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) < 1.0);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) > 0.0);
    TEST_ASSERT(((*fp1) & (*fp2)) == (*fp1));

    delete fp1;
    delete fp2;
    delete m1;
    delete m2;
  }

  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void test2Layers() {
  BOOST_LOG(rdInfoLog) << "testing advanced layered fps" << std::endl;
  {
    std::vector<unsigned int> atomCounts;
    RWMol *m1 = SmilesToMol("CC(C)C");

    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1);
    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m1);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) == 1.0);

    atomCounts.clear();
    atomCounts.resize(m1->getNumAtoms());
    for (unsigned int i = 0; i < m1->getNumAtoms(); ++i) {
      atomCounts[i] = 0;
    }

    delete fp2;
    fp2 = LayeredFingerprintMol(*m1, 0xFFFFFFFF, 1, 7, 2048, &atomCounts);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) == 1.0);
    TEST_ASSERT(atomCounts[0] == 4);
    TEST_ASSERT(atomCounts[1] == 7);
    TEST_ASSERT(atomCounts[2] == 4);
    TEST_ASSERT(atomCounts[3] == 4);

    delete fp2;
    fp2 = LayeredFingerprintMol(*m1, 0xFFFFFFFF, 1, 7, 2048, &atomCounts);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) == 1.0);
    TEST_ASSERT(atomCounts[0] == 8);
    TEST_ASSERT(atomCounts[1] == 14);
    TEST_ASSERT(atomCounts[2] == 8);
    TEST_ASSERT(atomCounts[3] == 8);

    delete fp1;
    delete fp2;
    delete m1;
  }

  {
    std::vector<unsigned int> atomCounts;
    RWMol *m1 = SmilesToMol("CC(C)C");
    RWMol *m2 = SmilesToMol("CCC");

    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1);
    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp2) < 1.0);

    atomCounts.clear();
    atomCounts.resize(m1->getNumAtoms());
    for (unsigned int i = 0; i < m1->getNumAtoms(); ++i) {
      atomCounts[i] = 0;
    }

    ExplicitBitVect *fp3 =
        LayeredFingerprintMol(*m1, 0xFFFFFFFF, 1, 7, 2048, &atomCounts, fp2);
    TEST_ASSERT(TanimotoSimilarity(*fp1, *fp3) < 1.0);
    TEST_ASSERT(atomCounts[0] == 3);
    TEST_ASSERT(atomCounts[1] == 6);
    TEST_ASSERT(atomCounts[2] == 3);
    TEST_ASSERT(atomCounts[3] == 3);

    delete fp1;
    delete fp2;
    delete fp3;
    delete m1;
    delete m2;
  }

  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void test3Layers() {
  BOOST_LOG(rdInfoLog) << "testing layered fps and queries" << std::endl;
  {
    RWMol *m1 = SmilesToMol("CC(C)C");
    RWMol *m2 = SmartsToMol("CC(C)C");

    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, 0x7, 1, 5, 256);
    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, 0x7, 1, 5, 256);
    TEST_ASSERT(fp2->getNumOnBits());

    ExplicitBitVect fp3 = (*fp1) & (*fp2);
#if 0
    std::cerr<<BitVectToText(*fp1)<<std::endl;
    std::cerr<<"---"<<std::endl;
    std::cerr<<BitVectToText(*fp2)<<std::endl;
    std::cerr<<BitVectToText(fp3)<<std::endl;
#endif
    TEST_ASSERT(fp3 == (*fp2));

    delete fp1;
    delete fp2;
    delete m1;
    delete m2;
  }

  {
    RWMol *m1 = SmilesToMol("CC(C)C");
    RWMol *m2 = SmartsToMol("C-C(-C)-C");

    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, 0x7, 1, 5, 256);
    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, 0x7, 1, 5, 256);
    TEST_ASSERT(fp2->getNumOnBits());

    ExplicitBitVect fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 == (*fp2));

    delete fp1;
    delete fp2;
    delete m1;
    delete m2;
  }

  {
    RWMol *m1 = SmilesToMol("CC(=C)C");
    RWMol *m2 = SmartsToMol("C-C(-C)-C");

    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, 0x7, 1, 5, 256);
    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, 0x7, 1, 5, 256);
    TEST_ASSERT(fp2->getNumOnBits());

    ExplicitBitVect fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 != (*fp2));
    TEST_ASSERT(fp3 != (*fp1));

    delete fp1;
    delete fp2;
    delete m1;
    delete m2;
  }

  {
    RWMol *m1 = SmilesToMol("CC(C)C");
    RWMol *m2 = SmartsToMol("CC([C,N])C");

    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, 0x7, 1, 5, 256);
    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, 0x7, 1, 5, 256);
    TEST_ASSERT(fp2->getNumOnBits());

    ExplicitBitVect fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 == (*fp2));

    delete fp1;
    delete fp2;
    delete m1;
    delete m2;
  }

  {
    RWMol *m1 = SmilesToMol("CC(C)C");
    RWMol *m2 = SmartsToMol("CC([!C])C");

    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, 0x7, 1, 5, 256);
    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, 0x7, 1, 5, 256);
    TEST_ASSERT(fp2->getNumOnBits());

    // the query says "!C", but we still match in the fp...
    ExplicitBitVect fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 == (*fp2));

    // of course we better match if the thing really isn't a C:
    delete fp1;
    delete m1;
    m1 = SmilesToMol("CC(O)C");
    fp1 = LayeredFingerprintMol(*m1, 0x7, 1, 5, 256);
    fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 == (*fp2));

    delete fp1;
    delete fp2;
    delete m1;
    delete m2;
  }

  {
    RWMol *m1 = SmilesToMol("CC(O)C");
    RWMol *m2 = SmartsToMol("CC([C,N])C");

    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, 0x7, 1, 5, 256);
    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, 0x7, 1, 5, 256);
    TEST_ASSERT(fp2->getNumOnBits());

    ExplicitBitVect fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 == (*fp2));

    delete fp1;
    delete fp2;
    delete m1;
    delete m2;
  }

  {
    RWMol *m1 = SmilesToMol("c1ccccc1");
    RWMol *m2 = SmartsToMol("cccc");
    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, 0x7, 1, 5, 256);
    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, 0x7, 1, 5, 256);
    TEST_ASSERT(fp2->getNumOnBits());

    ExplicitBitVect fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 == (*fp2));

    delete fp1;
    delete m1;
    // somewhat counter-intuitive result here, but this happens
    // because the aromaticity does not factor into the
    // calculation:
    m1 = SmilesToMol("C1CCCCC1");
    fp1 = LayeredFingerprintMol(*m1, 0x7, 1, 5, 256);
    fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 == (*fp2));

    delete fp1;
    delete fp2;
    delete m1;
    delete m2;
  }

  {
    RWMol *m1 = SmilesToMol("c1ccccc1");
    RWMol *m2 = SmartsToMol("c:c:c");
    ExplicitBitVect *fp1 = LayeredFingerprintMol(*m1, 0xFFFF, 1, 5, 512);
    ExplicitBitVect *fp2 = LayeredFingerprintMol(*m2, 0x5, 1, 5, 512);
    TEST_ASSERT(fp2->getNumOnBits());
    ExplicitBitVect fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 == (*fp2));

    delete fp1;
    delete m1;
    m1 = SmilesToMol("C1CCCCC1");
    fp1 = LayeredFingerprintMol(*m1, 0xFFFF, 1, 5, 512);
    fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 == (*fp2));
    delete fp2;
    fp2 = LayeredFingerprintMol(*m2, 0x7, 1, 5, 512);
    fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 == (*fp2));

    delete fp2;
    fp2 = LayeredFingerprintMol(*m2, 0x25, 1, 5, 512);
    fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 != (*fp2));

    delete fp2;
    fp2 = LayeredFingerprintMol(*m2, 0x7, 1, 5, 512);
    delete fp1;
    delete m1;
    // atom type information is factored in:
    m1 = SmilesToMol("c1ncncn1");
    fp1 = LayeredFingerprintMol(*m1, 0xFFFF, 1, 5, 512);
    fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 != (*fp2));

    delete fp2;
    delete m2;
    // but queries switch us back to generic types, so we match again:
    m2 = SmartsToMol("[C,N]:[C,N]:[C,N]");
    fp2 = LayeredFingerprintMol(*m2, 0x7, 1, 5, 512);
    TEST_ASSERT(fp2->getNumOnBits());
    fp3 = (*fp1) & (*fp2);
    TEST_ASSERT(fp3 == (*fp2));

    delete fp1;
    delete fp2;
    delete m1;
    delete m2;
  }

  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void test1MorganFPs() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test Morgan Fingerprints." << std::endl;

  {
    ROMol *mol;
    SparseIntVect<std::uint32_t> *fp;

    mol = SmilesToMol("CCCCC");
    fp = MorganFingerprints::getFingerprint(*mol, 0);
    TEST_ASSERT(fp->getNonzeroElements().size() == 2);
    delete fp;

    fp = MorganFingerprints::getFingerprint(*mol, 0, nullptr, nullptr, false,
                                            true, false);
    TEST_ASSERT(fp->getNonzeroElements().size() == 2);
    for (auto iter = fp->getNonzeroElements().begin();
         iter != fp->getNonzeroElements().end(); ++iter) {
      TEST_ASSERT(iter->second == 1);  // check that count == 1
    }
    delete fp;

    fp = MorganFingerprints::getHashedFingerprint(*mol, 0);
    TEST_ASSERT(fp->getNonzeroElements().size() == 2);
    delete fp;

    fp = MorganFingerprints::getFingerprint(*mol, 1);
    TEST_ASSERT(fp->getNonzeroElements().size() == 5);
    delete fp;
    fp = MorganFingerprints::getHashedFingerprint(*mol, 1);
    TEST_ASSERT(fp->getNonzeroElements().size() == 5);
    delete fp;

    fp = MorganFingerprints::getFingerprint(*mol, 2);
    TEST_ASSERT(fp->getNonzeroElements().size() == 7);
    delete fp;

    fp = MorganFingerprints::getFingerprint(*mol, 3);
    TEST_ASSERT(fp->getNonzeroElements().size() == 7);
    delete fp;

    delete mol;
  }
  {
    ROMol *mol;
    SparseIntVect<std::uint32_t> *fp;

    mol = SmilesToMol("O=C(O)CC1CC1");
    fp = MorganFingerprints::getFingerprint(*mol, 0);
    TEST_ASSERT(fp->getNonzeroElements().size() == 6);
    delete fp;
    fp = MorganFingerprints::getFingerprint(*mol, 1);
    TEST_ASSERT(fp->getNonzeroElements().size() == 12);
    delete fp;
    fp = MorganFingerprints::getFingerprint(*mol, 2);
    TEST_ASSERT(fp->getNonzeroElements().size() == 16);
    delete fp;
    fp = MorganFingerprints::getFingerprint(*mol, 3);
    TEST_ASSERT(fp->getNonzeroElements().size() == 17);
    delete fp;

    delete mol;
  }

  {
    // test that the results aren't order dependent, i.e. that we're
    // "canonicalizing" the fps correctly
    ROMol *mol, *mol2;
    SparseIntVect<std::uint32_t> *fp, *fp2;

    mol = SmilesToMol("O=C(O)CC1CC1");
    mol2 = SmilesToMol("OC(=O)CC1CC1");
    fp = MorganFingerprints::getFingerprint(*mol, 0);
    fp2 = MorganFingerprints::getFingerprint(*mol2, 0);
    TEST_ASSERT(fp->getNonzeroElements().size() == 6);
    TEST_ASSERT(fp2->getNonzeroElements().size() == 6);
    TEST_ASSERT(*fp == *fp2);
    delete fp;
    delete fp2;

    fp = MorganFingerprints::getFingerprint(*mol, 1);
    fp2 = MorganFingerprints::getFingerprint(*mol2, 1);
    TEST_ASSERT(fp->getNonzeroElements().size() == 12);
    TEST_ASSERT(fp2->getNonzeroElements().size() == 12);
    TEST_ASSERT(*fp == *fp2);
    delete fp;
    delete fp2;

    fp = MorganFingerprints::getFingerprint(*mol, 2);
    fp2 = MorganFingerprints::getFingerprint(*mol2, 2);
    TEST_ASSERT(fp->getNonzeroElements().size() == 16);
    TEST_ASSERT(fp2->getNonzeroElements().size() == 16);
    TEST_ASSERT(*fp == *fp2);
    delete fp;
    delete fp2;

    fp = MorganFingerprints::getFingerprint(*mol, 3);
    fp2 = MorganFingerprints::getFingerprint(*mol2, 3);
    TEST_ASSERT(fp->getNonzeroElements().size() == 17);
    TEST_ASSERT(fp2->getNonzeroElements().size() == 17);
    TEST_ASSERT(*fp == *fp2);
    delete fp;
    delete fp2;

    delete mol;
    delete mol2;
  }

  {
    // symmetry test:
    ROMol *mol;
    SparseIntVect<std::uint32_t> *fp;

    mol = SmilesToMol("OCCCCO");
    fp = MorganFingerprints::getFingerprint(*mol, 2);
    TEST_ASSERT(fp->getNonzeroElements().size() == 7);
    SparseIntVect<std::uint32_t>::StorageType::const_iterator iter;
    for (iter = fp->getNonzeroElements().begin();
         iter != fp->getNonzeroElements().end(); ++iter) {
      TEST_ASSERT(iter->second == 2 || iter->second == 4);
    }

    delete fp;
    delete mol;
  }

  {
    // chirality test:
    ROMol *mol;
    SparseIntVect<std::uint32_t> *fp;

    mol = SmilesToMol("CC(F)(Cl)C(F)(Cl)C");
    fp = MorganFingerprints::getFingerprint(*mol, 0);
    TEST_ASSERT(fp->getNonzeroElements().size() == 4);
    delete fp;
    fp = MorganFingerprints::getFingerprint(*mol, 1);
    TEST_ASSERT(fp->getNonzeroElements().size() == 8);
    delete mol;
    delete fp;

    mol = SmilesToMol("CC(F)(Cl)[C@](F)(Cl)C");
    fp = MorganFingerprints::getFingerprint(*mol, 0);
    TEST_ASSERT(fp->getNonzeroElements().size() == 4);
    delete fp;
    fp = MorganFingerprints::getFingerprint(*mol, 1);
    TEST_ASSERT(fp->getNonzeroElements().size() == 8);
    delete fp;
    fp = MorganFingerprints::getFingerprint(*mol, 0, nullptr, nullptr, true);
    TEST_ASSERT(fp->getNonzeroElements().size() == 4);
    delete fp;
    fp = MorganFingerprints::getFingerprint(*mol, 1, nullptr, nullptr, true);
    TEST_ASSERT(fp->getNonzeroElements().size() == 9);
    delete fp;
    delete mol;
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void test2MorganFPsFromAtoms() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog)
      << "    Test Morgan Fingerprints using fromAtoms argument." << std::endl;

  {
    ROMol *mol;
    SparseIntVect<std::uint32_t> *fp;
    std::vector<std::uint32_t> atoms;
    atoms.push_back(0);

    mol = SmilesToMol("CCCCC");
    fp = MorganFingerprints::getFingerprint(*mol, 0);
    TEST_ASSERT(fp->getNonzeroElements().size() == 2);
    delete fp;

    fp = MorganFingerprints::getFingerprint(
        *mol, 0, (std::vector<std::uint32_t> *)nullptr, &atoms);
    TEST_ASSERT(fp->getNonzeroElements().size() == 1);
    delete fp;

    fp = MorganFingerprints::getFingerprint(
        *mol, 1, (std::vector<std::uint32_t> *)nullptr, &atoms);
    TEST_ASSERT(fp->getNonzeroElements().size() == 2);
    delete fp;

    // tests issue 3415636
    fp = MorganFingerprints::getFingerprint(
        *mol, 2, (std::vector<std::uint32_t> *)nullptr, &atoms);
    TEST_ASSERT(fp->getNonzeroElements().size() == 3);
    delete fp;

    delete mol;
  }

  {
    ROMol *mol;
    SparseIntVect<std::uint32_t> *fp;
    std::vector<std::uint32_t> atoms;

    mol = SmilesToMol("CCCCC");
    fp = MorganFingerprints::getFingerprint(
        *mol, 0, (std::vector<std::uint32_t> *)nullptr, &atoms);
    TEST_ASSERT(fp->getNonzeroElements().size() == 0);
    delete fp;

    fp = MorganFingerprints::getFingerprint(
        *mol, 1, (std::vector<std::uint32_t> *)nullptr, &atoms);
    TEST_ASSERT(fp->getNonzeroElements().size() == 0);
    delete fp;

    delete mol;
  }

  {
    ROMol *mol;
    SparseIntVect<std::uint32_t> *fp;
    std::vector<std::uint32_t> atoms;
    atoms.push_back(0);

    mol = SmilesToMol("C(CC)CO");

    fp = MorganFingerprints::getFingerprint(
        *mol, 0, (std::vector<std::uint32_t> *)nullptr, &atoms);
    TEST_ASSERT(fp->getNonzeroElements().size() == 1);
    delete fp;

    fp = MorganFingerprints::getFingerprint(
        *mol, 1, (std::vector<std::uint32_t> *)nullptr, &atoms);
    TEST_ASSERT(fp->getNonzeroElements().size() == 2);
    delete fp;

    fp = MorganFingerprints::getFingerprint(
        *mol, 2, (std::vector<std::uint32_t> *)nullptr, &atoms);
    TEST_ASSERT(fp->getNonzeroElements().size() == 3);
    delete fp;

    // tests issue 3415636
    fp = MorganFingerprints::getFingerprint(
        *mol, 3, (std::vector<std::uint32_t> *)nullptr, &atoms);
    TEST_ASSERT(fp->getNonzeroElements().size() == 3);
    delete fp;

    delete mol;
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void test3MorganFPs() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test Morgan Fingerprints as bit vects."
                        << std::endl;

  {
    ROMol *mol;
    ExplicitBitVect *fp;

    mol = SmilesToMol("CCCCC");
    fp = MorganFingerprints::getFingerprintAsBitVect(*mol, 0, 2048);
    TEST_ASSERT(fp->getNumOnBits() == 2);
    delete fp;
    fp = MorganFingerprints::getFingerprintAsBitVect(*mol, 1, 2048);
    TEST_ASSERT(fp->getNumOnBits() == 5);
    delete fp;
    fp = MorganFingerprints::getFingerprintAsBitVect(*mol, 2, 2048);
    TEST_ASSERT(fp->getNumOnBits() == 7);
    delete fp;
    fp = MorganFingerprints::getFingerprintAsBitVect(*mol, 3, 2048);
    TEST_ASSERT(fp->getNumOnBits() == 7);
    delete fp;

    delete mol;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void test4MorganFPs() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog)
      << "    Test Morgan Fingerprints with feature invariants." << std::endl;

  {
    ROMol *mol;
    mol = SmilesToMol("Cc1ccccc1");
    TEST_ASSERT(mol);
    std::vector<std::uint32_t> invars(mol->getNumAtoms());
    MorganFingerprints::getFeatureInvariants(*mol, invars);
    TEST_ASSERT(invars[0] == 0);
    TEST_ASSERT(invars[1] != 0);
    TEST_ASSERT(invars[1] == invars[2]);
    TEST_ASSERT(invars[1] == invars[3]);
    TEST_ASSERT(invars[1] == invars[4]);
    TEST_ASSERT(invars[1] == invars[5]);
    TEST_ASSERT(invars[1] == invars[6]);
    delete mol;
  }
  {
    ROMol *mol;
    mol = SmilesToMol("FCCCl");
    TEST_ASSERT(mol);
    std::vector<std::uint32_t> invars(mol->getNumAtoms());
    MorganFingerprints::getFeatureInvariants(*mol, invars);
    TEST_ASSERT(invars[1] == invars[2]);
    TEST_ASSERT(invars[1] == 0);
    TEST_ASSERT(invars[0] == invars[3]);
    TEST_ASSERT(invars[0] != 0);
    delete mol;
  }
  {
    ROMol *mol;
    mol = SmilesToMol("Cc1ncccc1O");
    TEST_ASSERT(mol);
    std::vector<std::uint32_t> invars(mol->getNumAtoms());

    std::vector<const ROMol *> patterns(2);
    RWMol *p;
    p = SmartsToMol("[A]");
    patterns[0] = static_cast<const ROMol *>(p);
    p = SmartsToMol("[a]");
    patterns[1] = static_cast<const ROMol *>(p);

    MorganFingerprints::getFeatureInvariants(*mol, invars, &patterns);
    TEST_ASSERT(invars[0] != 0);
    TEST_ASSERT(invars[1] != 0);
    TEST_ASSERT(invars[0] != invars[1]);
    TEST_ASSERT(invars[1] == invars[2]);
    TEST_ASSERT(invars[0] == invars[7]);
    delete mol;
    delete patterns[0];
    delete patterns[1];
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void test5MorganFPs() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test additional Morgan fingerprints options."
                        << std::endl;

  {
    ROMol *m1, *m2;
    ExplicitBitVect *fp1, *fp2;
    std::vector<std::uint32_t> invars(3);
    invars[0] = 1;
    invars[1] = 1;
    invars[2] = 1;

    m1 = SmilesToMol("CCC");
    TEST_ASSERT(m1);
    m2 = SmilesToMol("CC=C");
    TEST_ASSERT(m2);

    fp1 = MorganFingerprints::getFingerprintAsBitVect(*m1, 2, 2048, &invars,
                                                      nullptr, false, true);
    invars[0] = 1;
    invars[1] = 1;
    invars[2] = 1;
    fp2 = MorganFingerprints::getFingerprintAsBitVect(*m2, 2, 2048, &invars,
                                                      nullptr, false, true);
    TEST_ASSERT((*fp1) != (*fp2));
    delete fp1;
    delete fp2;

    invars[0] = 1;
    invars[1] = 1;
    invars[2] = 1;
    fp1 = MorganFingerprints::getFingerprintAsBitVect(*m1, 2, 2048, &invars,
                                                      nullptr, false, false);
    invars[0] = 1;
    invars[1] = 1;
    invars[2] = 1;
    fp2 = MorganFingerprints::getFingerprintAsBitVect(*m2, 2, 2048, &invars,
                                                      nullptr, false, false);
    TEST_ASSERT((*fp1) == (*fp2));
    delete fp1;
    delete fp2;

    delete m1;
    delete m2;
  }

  {
    ROMol *m1, *m2, *m3;
    ExplicitBitVect *fp1, *fp2, *fp3;

    m1 = SmilesToMol("C[C@H](F)Cl");
    TEST_ASSERT(m1);
    m2 = SmilesToMol("C[C@@H](F)Cl");
    TEST_ASSERT(m2);
    m3 = SmilesToMol("CC(F)Cl");
    TEST_ASSERT(m3);

    fp1 = MorganFingerprints::getFingerprintAsBitVect(*m1, 2, 2048, nullptr,
                                                      nullptr, false, true);
    fp2 = MorganFingerprints::getFingerprintAsBitVect(*m2, 2, 2048, nullptr,
                                                      nullptr, false, true);
    fp3 = MorganFingerprints::getFingerprintAsBitVect(*m3, 2, 2048, nullptr,
                                                      nullptr, false, true);
    TEST_ASSERT((*fp1) == (*fp2));
    TEST_ASSERT((*fp1) == (*fp3));
    TEST_ASSERT((*fp2) == (*fp3));
    delete fp1;
    delete fp2;
    delete fp3;

    fp1 = MorganFingerprints::getFingerprintAsBitVect(*m1, 2, 2048, nullptr,
                                                      nullptr, true, true);
    fp2 = MorganFingerprints::getFingerprintAsBitVect(*m2, 2, 2048, nullptr,
                                                      nullptr, true, true);
    fp3 = MorganFingerprints::getFingerprintAsBitVect(*m3, 2, 2048, nullptr,
                                                      nullptr, true, true);
    TEST_ASSERT((*fp1) != (*fp2));
    TEST_ASSERT((*fp1) != (*fp3));
    TEST_ASSERT((*fp2) != (*fp3));
    delete fp1;
    delete fp2;
    delete fp3;

    delete m1;
    delete m2;
    delete m3;
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testIssue2875658() {
  BOOST_LOG(rdInfoLog) << "testing issue 2875658" << std::endl;

  RWMol *m;
  ExplicitBitVect *fp1, *fp2;

  m = SmilesToMol("c1ccccc1");
  fp1 = RDKFingerprintMol(*m, 1, 7, 2048, 4);
  delete m;
  m = SmilesToMol("c1cccnc1");
  fp2 = RDKFingerprintMol(*m, 1, 7, 2048, 4);
  delete m;

#if BOOST_VERSION / 100 >= 1040
  // bug fixes in the uniform_int<> distribution in version 1.40
  // necessitate this
  TEST_ASSERT(fp1->getNumOnBits() == 24);
  TEST_ASSERT((*fp1)[11]);
  TEST_ASSERT((*fp1)[857]);
  TEST_ASSERT((*fp1)[1786]);
  TEST_ASSERT((*fp1)[2020]);

  TEST_ASSERT(fp2->getNumOnBits() == 64);
  TEST_ASSERT((*fp2)[11]);
  TEST_ASSERT((*fp2)[179]);
  TEST_ASSERT((*fp2)[1878]);
  TEST_ASSERT((*fp2)[2020]);
#else
  TEST_ASSERT(fp1->getNumOnBits() == 24);
  TEST_ASSERT((*fp1)[23]);
  TEST_ASSERT((*fp1)[434]);
  TEST_ASSERT((*fp1)[1445]);
  TEST_ASSERT((*fp1)[2031]);

  TEST_ASSERT(fp2->getNumOnBits() == 62);
  TEST_ASSERT((*fp2)[23]);
  TEST_ASSERT((*fp2)[173]);
  TEST_ASSERT((*fp2)[1847]);
  TEST_ASSERT((*fp2)[1975]);
#endif
  delete fp1;
  delete fp2;
}

void testAtomCodes() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test Atom Codes." << std::endl;

  ROMol *mol;
  std::uint32_t tgt;
  mol = SmilesToMol("C=C");
  TEST_ASSERT(AtomPairs::getAtomCode(mol->getAtomWithIdx(0)) ==
              AtomPairs::getAtomCode(mol->getAtomWithIdx(1)));
  tgt = 1 | (1 | 1 << AtomPairs::numPiBits) << AtomPairs::numBranchBits;
  TEST_ASSERT(AtomPairs::getAtomCode(mol->getAtomWithIdx(0)) == tgt);
  tgt = 1 << AtomPairs::numBranchBits |
        1 << (AtomPairs::numBranchBits + AtomPairs::numPiBits);
  TEST_ASSERT(AtomPairs::getAtomCode(mol->getAtomWithIdx(0), 1) == tgt);

  delete mol;
  mol = SmilesToMol("C#CO");
  tgt = 1 | 2 << AtomPairs::numBranchBits |
        1 << (AtomPairs::numBranchBits + AtomPairs::numPiBits);
  TEST_ASSERT(AtomPairs::getAtomCode(mol->getAtomWithIdx(0)) == tgt);
  tgt = 2 | 2 << AtomPairs::numBranchBits |
        1 << (AtomPairs::numBranchBits + AtomPairs::numPiBits);
  TEST_ASSERT(AtomPairs::getAtomCode(mol->getAtomWithIdx(1)) == tgt);
  tgt = 1 | 0 << AtomPairs::numBranchBits |
        3 << (AtomPairs::numBranchBits + AtomPairs::numPiBits);
  TEST_ASSERT(AtomPairs::getAtomCode(mol->getAtomWithIdx(2)) == tgt);

  delete mol;
  mol = SmilesToMol("CC(O)C(O)(O)C");
  tgt = 1 | 0 << AtomPairs::numBranchBits |
        1 << (AtomPairs::numBranchBits + AtomPairs::numPiBits);
  TEST_ASSERT(AtomPairs::getAtomCode(mol->getAtomWithIdx(1), 2) == tgt);
  tgt = 2 | 0 << AtomPairs::numBranchBits |
        1 << (AtomPairs::numBranchBits + AtomPairs::numPiBits);
  TEST_ASSERT(AtomPairs::getAtomCode(mol->getAtomWithIdx(3), 2) == tgt);

  delete mol;
  mol = SmilesToMol("C=CC(=O)O");
  tgt = 0 | 0 << AtomPairs::numBranchBits |
        3 << (AtomPairs::numBranchBits + AtomPairs::numPiBits);
  TEST_ASSERT(AtomPairs::getAtomCode(mol->getAtomWithIdx(4), 1) == tgt);
  tgt = 3 | 1 << AtomPairs::numBranchBits |
        1 << (AtomPairs::numBranchBits + AtomPairs::numPiBits);
  TEST_ASSERT(AtomPairs::getAtomCode(mol->getAtomWithIdx(2)) == tgt);

  delete mol;
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testAtomPairs() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test Atom Pairs." << std::endl;

  ROMol *mol;
  SparseIntVect<std::int32_t> *fp;
  std::uint32_t tgt;
  std::uint32_t c1, c2, c3;

  mol = SmilesToMol("CCCCC");
  c1 = AtomPairs::getAtomCode(mol->getAtomWithIdx(0));
  c2 = AtomPairs::getAtomCode(mol->getAtomWithIdx(1));
  c3 = AtomPairs::getAtomCode(mol->getAtomWithIdx(2));
  tgt = 1 | (std::min(c1, c2) | std::max(c1, c2) << AtomPairs::codeSize)
                << AtomPairs::numPathBits;
  TEST_ASSERT(AtomPairs::getAtomPairCode(c1, c2, 1) == tgt);
  TEST_ASSERT(AtomPairs::getAtomPairCode(c2, c1, 1) == tgt);
  tgt = 2 | (std::min(c1, c3) | std::max(c1, c3) << AtomPairs::codeSize)
                << AtomPairs::numPathBits;
  TEST_ASSERT(AtomPairs::getAtomPairCode(c1, c3, 2) == tgt);
  TEST_ASSERT(AtomPairs::getAtomPairCode(c3, c1, 2) == tgt);

  delete mol;
  mol = SmilesToMol("CCC");
  fp = AtomPairs::getAtomPairFingerprint(*mol);
  TEST_ASSERT(fp->getTotalVal() == 3);
  TEST_ASSERT(fp->getNonzeroElements().size() == 2);

  c1 = AtomPairs::getAtomCode(mol->getAtomWithIdx(0));
  c2 = AtomPairs::getAtomCode(mol->getAtomWithIdx(1));
  c3 = AtomPairs::getAtomCode(mol->getAtomWithIdx(2));
  TEST_ASSERT(fp->getVal(AtomPairs::getAtomPairCode(c1, c2, 1)) == 2);
  TEST_ASSERT(fp->getVal(AtomPairs::getAtomPairCode(c1, c3, 2)) == 1);

  delete mol;
  delete fp;
  mol = SmilesToMol("CC=O.Cl");
  fp = AtomPairs::getAtomPairFingerprint(*mol);
  TEST_ASSERT(fp->getTotalVal() == 3);
  TEST_ASSERT(fp->getNonzeroElements().size() == 3);

  c1 = AtomPairs::getAtomCode(mol->getAtomWithIdx(0));
  c2 = AtomPairs::getAtomCode(mol->getAtomWithIdx(1));
  c3 = AtomPairs::getAtomCode(mol->getAtomWithIdx(2));
  TEST_ASSERT(fp->getVal(AtomPairs::getAtomPairCode(c1, c2, 1)) == 1);
  TEST_ASSERT(fp->getVal(AtomPairs::getAtomPairCode(c1, c2, 1)) == 1);
  TEST_ASSERT(fp->getVal(AtomPairs::getAtomPairCode(c2, c3, 1)) == 1);

  delete mol;
  delete fp;
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testAtomPairs2() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test Atom Pairs part 2." << std::endl;

  {
    ROMol *mol;
    SparseIntVect<std::int32_t> *fp;

    mol = SmilesToMol("CCC");
    fp = AtomPairs::getAtomPairFingerprint(*mol, 1, 2);
    TEST_ASSERT(fp->getTotalVal() == 3);
    TEST_ASSERT(fp->getNonzeroElements().size() == 2);

    delete fp;
    fp = AtomPairs::getAtomPairFingerprint(*mol, 2, 2);
    TEST_ASSERT(fp->getTotalVal() == 1);
    TEST_ASSERT(fp->getNonzeroElements().size() == 1);
    delete fp;
    delete mol;
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testHashedAtomPairs() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test Hashed Atom Pairs." << std::endl;

  {
    ROMol *mol;
    mol = SmilesToMol("c1ccccc1");
    SparseIntVect<std::int32_t> *fp1;
    fp1 = AtomPairs::getHashedAtomPairFingerprint(*mol);
    SparseIntVect<std::int32_t> *fp2;
    fp2 = AtomPairs::getHashedAtomPairFingerprint(*mol);
    TEST_ASSERT(DiceSimilarity(*fp1, *fp2) == 1.0);
    TEST_ASSERT(*fp1 == *fp2);

    delete mol;
    delete fp2;
    mol = SmilesToMol("c1ccccn1");
    fp2 = AtomPairs::getHashedAtomPairFingerprint(*mol);
    RANGE_CHECK(0.0, DiceSimilarity(*fp1, *fp2), 1.0);

    delete mol;
    delete fp1;
    delete fp2;
  }

  {
    ROMol *mol;
    mol = SmilesToMol("c1ccccc1");
    SparseIntVect<std::int32_t> *fp1;
    fp1 = AtomPairs::getHashedAtomPairFingerprint(*mol, 2048);
    SparseIntVect<std::int32_t> *fp2;
    fp2 = AtomPairs::getHashedAtomPairFingerprint(*mol, 2048, 1, 3);
    TEST_ASSERT(DiceSimilarity(*fp1, *fp2) == 1.0);
    TEST_ASSERT(*fp1 == *fp2);

    delete fp2;
    fp2 = AtomPairs::getHashedAtomPairFingerprint(*mol, 2048, 1, 2);
    RANGE_CHECK(0.0, DiceSimilarity(*fp1, *fp2), 1.0);

    delete mol;
    delete fp1;
    delete fp2;
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testTorsions() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test Topological Torsions." << std::endl;

  ROMol *mol;
  SparseIntVect<boost::int64_t> *fp;
  boost::uint64_t tgt;
  boost::uint64_t c1, c2, c3, c4;
  std::vector<std::uint32_t> codes;

  mol = SmilesToMol("CCCC");
  c1 = AtomPairs::getAtomCode(mol->getAtomWithIdx(0)) - 1;
  c2 = AtomPairs::getAtomCode(mol->getAtomWithIdx(1)) - 2;
  c3 = AtomPairs::getAtomCode(mol->getAtomWithIdx(2)) - 2;
  c4 = AtomPairs::getAtomCode(mol->getAtomWithIdx(3)) - 1;
  tgt = c1 | (c2 | (c3 | c4 << AtomPairs::codeSize) << AtomPairs::codeSize)
                 << AtomPairs::codeSize;
  codes.clear();
  codes.push_back(static_cast<unsigned int>(c1));
  codes.push_back(static_cast<unsigned int>(c2));
  codes.push_back(static_cast<unsigned int>(c3));
  codes.push_back(static_cast<unsigned int>(c4));
  TEST_ASSERT(AtomPairs::getTopologicalTorsionCode(codes) == tgt);

  fp = AtomPairs::getTopologicalTorsionFingerprint(*mol);
  TEST_ASSERT(fp->getTotalVal() == 1);
  TEST_ASSERT(fp->getNonzeroElements().size() == 1);

  delete mol;
  delete fp;
  mol = SmilesToMol("CCCCO.Cl");
  fp = AtomPairs::getTopologicalTorsionFingerprint(*mol);
  TEST_ASSERT(fp->getTotalVal() == 2);
  TEST_ASSERT(fp->getNonzeroElements().size() == 2);

  delete fp;
  fp = AtomPairs::getTopologicalTorsionFingerprint(*mol, 3);
  TEST_ASSERT(fp->getTotalVal() == 3);
  TEST_ASSERT(fp->getNonzeroElements().size() == 3);

  delete mol;
  delete fp;
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testHashedTorsions() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test Hashed torsions." << std::endl;

  {
    ROMol *mol;
    mol = SmilesToMol("c1ccccc1");
    SparseIntVect<boost::int64_t> *fp1;
    fp1 = AtomPairs::getHashedTopologicalTorsionFingerprint(*mol);
    SparseIntVect<boost::int64_t> *fp2;
    fp2 = AtomPairs::getHashedTopologicalTorsionFingerprint(*mol);
    TEST_ASSERT(DiceSimilarity(*fp1, *fp2) == 1.0);
    TEST_ASSERT(*fp1 == *fp2);

    delete mol;
    delete fp2;
    mol = SmilesToMol("c1ccccn1");
    fp2 = AtomPairs::getHashedTopologicalTorsionFingerprint(*mol);
    RANGE_CHECK(0.0, DiceSimilarity(*fp1, *fp2), 1.0);

    delete mol;
    delete fp1;
    delete fp2;
  }

  {
    ROMol *mol;
    mol = SmilesToMol("c1ccccc1");
    SparseIntVect<boost::int64_t> *fp1;
    fp1 = AtomPairs::getHashedTopologicalTorsionFingerprint(*mol, 2048, 6);
    SparseIntVect<boost::int64_t> *fp2;
    fp2 = AtomPairs::getHashedTopologicalTorsionFingerprint(*mol, 2048, 6);
    TEST_ASSERT(DiceSimilarity(*fp1, *fp2) == 1.0);
    TEST_ASSERT(*fp1 == *fp2);

    delete mol;
    delete fp2;
    mol = SmilesToMol("c1ccccn1");
    fp2 = AtomPairs::getHashedTopologicalTorsionFingerprint(*mol, 2048, 6);
    RANGE_CHECK(0.0, DiceSimilarity(*fp1, *fp2), 1.0);

    delete mol;
    delete fp1;
    delete fp2;
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testBulkTorsions() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test Bulk Topological Torsions." << std::endl;

  std::string fName = getenv("RDBASE");
  fName += "/Projects/DbCLI/testData/pubchem.200.sdf";
  SDMolSupplier suppl(fName);
  while (!suppl.atEnd()) {
    ROMol *mol = suppl.next();
    SparseIntVect<boost::int64_t> *fp;
    fp = AtomPairs::getTopologicalTorsionFingerprint(*mol);
    TEST_ASSERT(fp->getTotalVal() > 1);
    delete mol;
    delete fp;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testRootedAtomPairs() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test Rooted Atom Pairs." << std::endl;

  ROMol *mol;
  SparseIntVect<std::int32_t> *fp1, *fp2;
  std::vector<std::uint32_t> roots;

  mol = SmilesToMol("OCCCCC");
  fp1 = AtomPairs::getAtomPairFingerprint(*mol);
  SparseIntVect<std::int32_t>::StorageType nz1 = fp1->getNonzeroElements();
  TEST_ASSERT(nz1.size() > 0);

  roots.push_back(0);
  fp2 = AtomPairs::getAtomPairFingerprint(*mol, &roots);
  SparseIntVect<std::int32_t>::StorageType nz2 = fp2->getNonzeroElements();
  TEST_ASSERT(nz2.size() > 0);
  TEST_ASSERT(nz2.size() < nz1.size());

  for (SparseIntVect<std::int32_t>::StorageType::const_iterator bIt =
           nz2.begin();
       bIt != nz2.end(); ++bIt) {
    TEST_ASSERT(bIt->second <= fp2->getVal(bIt->first));
  }

  delete mol;
  delete fp1;
  delete fp2;

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testIgnoreAtomPairs() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test ignoring atoms in Atom Pairs."
                        << std::endl;

  {
    ROMol *mol;
    SparseIntVect<std::int32_t> *fp1, *fp2;
    std::vector<std::uint32_t> roots;

    mol = SmilesToMol("OCCCCC");
    fp1 = AtomPairs::getAtomPairFingerprint(*mol, 1, 5);
    SparseIntVect<std::int32_t>::StorageType nz1 = fp1->getNonzeroElements();
    TEST_ASSERT(nz1.size() > 0);

    roots.push_back(0);
    fp2 = AtomPairs::getAtomPairFingerprint(*mol, 1, 5, nullptr, &roots);
    SparseIntVect<std::int32_t>::StorageType nz2 = fp2->getNonzeroElements();
    TEST_ASSERT(nz2.size() == nz1.size() - 5);

    for (SparseIntVect<std::int32_t>::StorageType::const_iterator bIt =
             nz2.begin();
         bIt != nz2.end(); ++bIt) {
      TEST_ASSERT(bIt->second <= fp2->getVal(bIt->first));
    }

    delete mol;
    delete fp1;
    delete fp2;
  }
  {
    ROMol *mol;
    SparseIntVect<std::int32_t> *fp2;
    std::vector<std::uint32_t> roots;

    mol = SmilesToMol("OCCCCC");
    roots.push_back(0);
    fp2 = AtomPairs::getAtomPairFingerprint(*mol, 1, 5, &roots, &roots);
    SparseIntVect<std::int32_t>::StorageType nz2 = fp2->getNonzeroElements();
    TEST_ASSERT(nz2.size() == 0);

    delete mol;
    delete fp2;
  }

  {
    ROMol *mol;
    SparseIntVect<std::int32_t> *fp1, *fp2;
    std::vector<std::uint32_t> roots;

    mol = SmilesToMol("OCCCCC");
    fp1 = AtomPairs::getHashedAtomPairFingerprint(*mol, 4096, 1, 5);
    SparseIntVect<std::int32_t>::StorageType nz1 = fp1->getNonzeroElements();
    TEST_ASSERT(nz1.size() > 0);

    roots.push_back(0);
    fp2 = AtomPairs::getHashedAtomPairFingerprint(*mol, 4096, 1, 5, nullptr,
                                                  &roots);
    SparseIntVect<std::int32_t>::StorageType nz2 = fp2->getNonzeroElements();
    TEST_ASSERT(nz2.size() < nz1.size());

    for (SparseIntVect<std::int32_t>::StorageType::const_iterator bIt =
             nz2.begin();
         bIt != nz2.end(); ++bIt) {
      TEST_ASSERT(bIt->second <= fp2->getVal(bIt->first));
    }

    delete mol;
    delete fp1;
    delete fp2;
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testRootedTorsions() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test Rooted Topological Torsions." << std::endl;

  ROMol *mol;
  SparseIntVect<boost::int64_t> *fp1, *fp2;
  std::vector<std::uint32_t> roots;

  mol = SmilesToMol("OCCCC");
  roots.push_back(0);

  fp1 = AtomPairs::getTopologicalTorsionFingerprint(*mol);
  SparseIntVect<boost::int64_t>::StorageType nz1 = fp1->getNonzeroElements();
  TEST_ASSERT(nz1.size() > 0);

  fp2 = AtomPairs::getTopologicalTorsionFingerprint(*mol, 4, &roots);
  SparseIntVect<boost::int64_t>::StorageType nz2 = fp2->getNonzeroElements();
  TEST_ASSERT(nz2.size() > 0);
  TEST_ASSERT(nz2.size() < nz1.size());

  for (SparseIntVect<boost::int64_t>::StorageType::const_iterator bIt =
           nz2.begin();
       bIt != nz2.end(); ++bIt) {
    TEST_ASSERT(bIt->second <= fp2->getVal(bIt->first));
  }

  delete mol;
  delete fp1;
  delete fp2;
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testIgnoreTorsions() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test ignoring atoms in Topological Torsions."
                        << std::endl;

  {
    ROMol *mol;
    SparseIntVect<boost::int64_t> *fp1, *fp2;
    std::vector<std::uint32_t> roots;

    mol = SmilesToMol("OCCCC");
    roots.push_back(0);

    fp1 = AtomPairs::getTopologicalTorsionFingerprint(*mol);
    SparseIntVect<boost::int64_t>::StorageType nz1 = fp1->getNonzeroElements();
    TEST_ASSERT(nz1.size() == 2);

    fp2 = AtomPairs::getTopologicalTorsionFingerprint(*mol, 4, nullptr, &roots);
    SparseIntVect<boost::int64_t>::StorageType nz2 = fp2->getNonzeroElements();
    TEST_ASSERT(nz2.size() == 1);

    for (SparseIntVect<boost::int64_t>::StorageType::const_iterator bIt =
             nz2.begin();
         bIt != nz2.end(); ++bIt) {
      TEST_ASSERT(bIt->second <= fp2->getVal(bIt->first));
    }

    delete mol;
    delete fp1;
    delete fp2;
  }
  {
    ROMol *mol;
    SparseIntVect<boost::int64_t> *fp2;
    std::vector<std::uint32_t> roots;

    mol = SmilesToMol("OCCCC");
    roots.push_back(1);

    fp2 = AtomPairs::getTopologicalTorsionFingerprint(*mol, 4, nullptr, &roots);
    SparseIntVect<boost::int64_t>::StorageType nz2 = fp2->getNonzeroElements();
    TEST_ASSERT(nz2.size() == 0);

    delete mol;
    delete fp2;
  }

  {
    ROMol *mol;
    SparseIntVect<boost::int64_t> *fp2;
    std::vector<std::uint32_t> roots;

    mol = SmilesToMol("OCCCC");
    roots.push_back(0);

    fp2 = AtomPairs::getTopologicalTorsionFingerprint(*mol, 4, &roots, &roots);
    SparseIntVect<boost::int64_t>::StorageType nz2 = fp2->getNonzeroElements();
    TEST_ASSERT(nz2.size() == 0);

    delete mol;
    delete fp2;
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testMorganAtomInfo() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test atom info from morgan fingerprints."
                        << std::endl;

  {
    ROMol *mol;
    SparseIntVect<std::uint32_t> *fp;
    MorganFingerprints::BitInfoMap bitInfo;
    SparseIntVect<std::uint32_t>::StorageType nze;

    mol = SmilesToMol("CCCCC");
    fp = MorganFingerprints::getFingerprint(*mol, 0, nullptr, nullptr, false,
                                            true, true, false, &bitInfo);
    nze = fp->getNonzeroElements();
    TEST_ASSERT(nze.size() == 2);
    TEST_ASSERT(bitInfo.size() == 2);
    for (SparseIntVect<std::uint32_t>::StorageType::const_iterator iter =
             nze.begin();
         iter != nze.end(); ++iter) {
      TEST_ASSERT(iter->second == rdcast<int>(bitInfo[iter->first].size()));
    }
    for (MorganFingerprints::BitInfoMap::const_iterator iter = bitInfo.begin();
         iter != bitInfo.end(); ++iter) {
      TEST_ASSERT(iter->second.begin()->second == 0);
    }

    delete fp;

    bitInfo.clear();
    fp = MorganFingerprints::getFingerprint(*mol, 1, nullptr, nullptr, false,
                                            true, true, false, &bitInfo);
    TEST_ASSERT(fp->getNonzeroElements().size() == 5);
    for (SparseIntVect<std::uint32_t>::StorageType::const_iterator iter =
             nze.begin();
         iter != nze.end(); ++iter) {
      TEST_ASSERT(iter->second == rdcast<int>(bitInfo[iter->first].size()));
    }
    for (MorganFingerprints::BitInfoMap::const_iterator iter = bitInfo.begin();
         iter != bitInfo.end(); ++iter) {
      TEST_ASSERT(iter->second.begin()->second == 0 ||
                  iter->second.begin()->second == 1);
    }
    delete fp;

    delete mol;
  }

  {
    ROMol *mol;
    ExplicitBitVect *fp;
    MorganFingerprints::BitInfoMap bitInfo;

    mol = SmilesToMol("CCCCC");
    fp = MorganFingerprints::getFingerprintAsBitVect(
        *mol, 0, 2048, nullptr, nullptr, false, true, false, &bitInfo);
    TEST_ASSERT(fp->getNumOnBits() == 2);
    TEST_ASSERT(bitInfo.size() == 2);
    for (MorganFingerprints::BitInfoMap::const_iterator iter = bitInfo.begin();
         iter != bitInfo.end(); ++iter) {
      TEST_ASSERT(iter->first < 2048);
      TEST_ASSERT(fp->getBit(iter->first));
    }
    for (MorganFingerprints::BitInfoMap::const_iterator iter = bitInfo.begin();
         iter != bitInfo.end(); ++iter) {
      TEST_ASSERT(iter->second.begin()->second == 0);
    }

    delete fp;
    bitInfo.clear();
    fp = MorganFingerprints::getFingerprintAsBitVect(
        *mol, 1, 2048, nullptr, nullptr, false, true, false, &bitInfo);
    TEST_ASSERT(fp->getNumOnBits() == 5);
    TEST_ASSERT(bitInfo.size() == 5);
    for (MorganFingerprints::BitInfoMap::const_iterator iter = bitInfo.begin();
         iter != bitInfo.end(); ++iter) {
      TEST_ASSERT(iter->first < 2048);
      TEST_ASSERT(fp->getBit(iter->first));
    }
    for (MorganFingerprints::BitInfoMap::const_iterator iter = bitInfo.begin();
         iter != bitInfo.end(); ++iter) {
      TEST_ASSERT(iter->second.begin()->second == 0 ||
                  iter->second.begin()->second == 1);
    }
    delete fp;

    delete mol;
  }

  {  // this was github issue #295

    ROMol *mol;
    MorganFingerprints::BitInfoMap bitInfo1, bitInfo2;

    mol = SmilesToMol("CCCCC");

    ExplicitBitVect *fp;
    fp = MorganFingerprints::getFingerprintAsBitVect(
        *mol, 2, 2048, nullptr, nullptr, false, true, false, &bitInfo1);
    delete fp;

    SparseIntVect<std::uint32_t> *iv;
    iv = MorganFingerprints::getHashedFingerprint(
        *mol, 2, 2048, nullptr, nullptr, false, true, false, &bitInfo2);
    delete iv;

    TEST_ASSERT(bitInfo1.size() == bitInfo2.size());

    for (MorganFingerprints::BitInfoMap::const_iterator iter1 =
             bitInfo1.begin();
         iter1 != bitInfo1.end(); ++iter1) {
      TEST_ASSERT(iter1->first < 2048);
      TEST_ASSERT(bitInfo2.find(iter1->first) != bitInfo2.end());
    }

    delete mol;
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testMorganAtomInfoRedundantEnv() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test atom info from morgan fingerprints "
                           "including Info Redundant Environments."
                        << std::endl;

  {
    ROMol *mol;
    SparseIntVect<std::uint32_t> *fp;
    MorganFingerprints::BitInfoMap bitInfo;
    SparseIntVect<std::uint32_t>::StorageType nze;

    mol = SmilesToMol("CCCC(N)(O)");

    fp = MorganFingerprints::getFingerprint(*mol, 2, nullptr, nullptr, false,
                                            true, true, false, &bitInfo, false);

    TEST_ASSERT(bitInfo.size() == 14);

    delete fp;

    bitInfo.clear();
    fp = MorganFingerprints::getFingerprint(*mol, 2, nullptr, nullptr, false,
                                            true, true, false, &bitInfo, true);
    TEST_ASSERT(bitInfo.size() == 17);

    delete fp;

    delete mol;
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testRDKitFPOptions() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdInfoLog) << "testing RDKit fingerprint options" << std::endl;
  {
    std::string smi = "C1=CC=CC=C1";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    smi = "C1=CC=CC=N1";
    RWMol *m2 = SmilesToMol(smi);
    TEST_ASSERT(m2);
    ExplicitBitVect *fp1 = RDKFingerprintMol(*m1);
    ExplicitBitVect *fp2 = RDKFingerprintMol(*m2);
    TEST_ASSERT(*fp1 != *fp2);
    delete m1;
    delete m2;
    delete fp1;
    delete fp2;
  }
  {
    UINT_VECT invars(6, 1);
    std::string smi = "C1=CC=CC=C1";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    smi = "C1=CC=CC=N1";
    RWMol *m2 = SmilesToMol(smi);
    TEST_ASSERT(m2);
    ExplicitBitVect *fp1 = RDKFingerprintMol(*m1, 1, 7, 2048, 2, true, 0, 128,
                                             true, true, &invars);
    ExplicitBitVect *fp2 = RDKFingerprintMol(*m2, 1, 7, 2048, 2, true, 0, 128,
                                             true, true, &invars);
    TEST_ASSERT(*fp1 == *fp2);
    delete m1;
    delete m2;
    delete fp1;
    delete fp2;
  }
  {
    UINT_VECT invars(6, 1);
    std::string smi = "C1=CC=CC=C1";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    smi = "C1CCCCN1";
    RWMol *m2 = SmilesToMol(smi);
    TEST_ASSERT(m2);
    ExplicitBitVect *fp1 = RDKFingerprintMol(*m1, 1, 7, 2048, 2, true, 0, 128,
                                             true, false, &invars);
    ExplicitBitVect *fp2 = RDKFingerprintMol(*m2, 1, 7, 2048, 2, true, 0, 128,
                                             true, false, &invars);
    TEST_ASSERT(*fp1 == *fp2);
    delete m1;
    delete m2;
    delete fp1;
    delete fp2;
  }
  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void testPairsAndTorsionsOptions() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdInfoLog) << "testing atom pair and torsions options" << std::endl;
  {
    std::string smi = "C1=CC=CC=C1";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    smi = "C1=CC=CC=N1";
    RWMol *m2 = SmilesToMol(smi);
    TEST_ASSERT(m2);
    SparseIntVect<std::int32_t> *fp1 = AtomPairs::getAtomPairFingerprint(*m1);
    SparseIntVect<std::int32_t> *fp2 = AtomPairs::getAtomPairFingerprint(*m2);
    TEST_ASSERT(*fp1 != *fp2);
    delete fp1;
    delete fp2;

    UINT_VECT invars(6, 1);
    fp1 = AtomPairs::getAtomPairFingerprint(
        *m1, (const std::vector<std::uint32_t> *)nullptr,
        (const std::vector<std::uint32_t> *)nullptr, &invars);
    fp2 = AtomPairs::getAtomPairFingerprint(
        *m1, (const std::vector<std::uint32_t> *)nullptr,
        (const std::vector<std::uint32_t> *)nullptr, &invars);

    TEST_ASSERT(*fp1 == *fp2);
    delete m1;
    delete m2;
    delete fp1;
    delete fp2;
  }
  {
    std::string smi = "C1=CC=CC=C1";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    smi = "C1=CC=CC=N1";
    RWMol *m2 = SmilesToMol(smi);
    TEST_ASSERT(m2);
    SparseIntVect<std::int32_t> *fp1 =
        AtomPairs::getHashedAtomPairFingerprint(*m1, 1024, 1, 5);
    SparseIntVect<std::int32_t> *fp2 =
        AtomPairs::getHashedAtomPairFingerprint(*m2, 1024, 1, 5);
    TEST_ASSERT(*fp1 != *fp2);
    delete fp1;
    delete fp2;

    UINT_VECT invars(6, 1);
    fp1 = AtomPairs::getHashedAtomPairFingerprint(
        *m1, 1024, 1, 5, (const std::vector<std::uint32_t> *)nullptr,
        (const std::vector<std::uint32_t> *)nullptr, &invars);
    fp2 = AtomPairs::getHashedAtomPairFingerprint(
        *m2, 1024, 1, 5, (const std::vector<std::uint32_t> *)nullptr,
        (const std::vector<std::uint32_t> *)nullptr, &invars);

    TEST_ASSERT(*fp1 == *fp2);
    delete m1;
    delete m2;
    delete fp1;
    delete fp2;
  }
  {
    std::string smi = "C1=CC=CC=C1";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    smi = "C1=CC=CC=N1";
    RWMol *m2 = SmilesToMol(smi);
    TEST_ASSERT(m2);
    ExplicitBitVect *fp1 =
        AtomPairs::getHashedAtomPairFingerprintAsBitVect(*m1, 1024, 1, 5);
    ExplicitBitVect *fp2 =
        AtomPairs::getHashedAtomPairFingerprintAsBitVect(*m2, 1024, 1, 5);
    TEST_ASSERT(*fp1 != *fp2);
    delete fp1;
    delete fp2;

    UINT_VECT invars(6, 1);
    fp1 = AtomPairs::getHashedAtomPairFingerprintAsBitVect(
        *m1, 1024, 1, 5, (const std::vector<std::uint32_t> *)nullptr,
        (const std::vector<std::uint32_t> *)nullptr, &invars);
    fp2 = AtomPairs::getHashedAtomPairFingerprintAsBitVect(
        *m2, 1024, 1, 5, (const std::vector<std::uint32_t> *)nullptr,
        (const std::vector<std::uint32_t> *)nullptr, &invars);

    TEST_ASSERT(*fp1 == *fp2);
    delete m1;
    delete m2;
    delete fp1;
    delete fp2;
  }
  {
    std::string smi = "C1=CC=CC=C1";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    smi = "C1=CC=CC=N1";
    RWMol *m2 = SmilesToMol(smi);
    TEST_ASSERT(m2);
    SparseIntVect<boost::int64_t> *fp1 =
        AtomPairs::getTopologicalTorsionFingerprint(*m1);
    SparseIntVect<boost::int64_t> *fp2 =
        AtomPairs::getTopologicalTorsionFingerprint(*m2);
    TEST_ASSERT(*fp1 != *fp2);
    delete fp1;
    delete fp2;

    UINT_VECT invars(6, 1);
    fp1 = AtomPairs::getTopologicalTorsionFingerprint(
        *m1, 4, (const std::vector<std::uint32_t> *)nullptr,
        (const std::vector<std::uint32_t> *)nullptr, &invars);
    fp2 = AtomPairs::getTopologicalTorsionFingerprint(
        *m2, 4, (const std::vector<std::uint32_t> *)nullptr,
        (const std::vector<std::uint32_t> *)nullptr, &invars);

    TEST_ASSERT(*fp1 == *fp2);
    delete m1;
    delete m2;
    delete fp1;
    delete fp2;
  }
  {
    std::string smi = "C1=CC=CC=C1";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    smi = "C1=CC=CC=N1";
    RWMol *m2 = SmilesToMol(smi);
    TEST_ASSERT(m2);
    SparseIntVect<boost::int64_t> *fp1 =
        AtomPairs::getHashedTopologicalTorsionFingerprint(*m1);
    SparseIntVect<boost::int64_t> *fp2 =
        AtomPairs::getHashedTopologicalTorsionFingerprint(*m2);

    TEST_ASSERT(*fp1 != *fp2);
    delete fp1;
    delete fp2;

    UINT_VECT invars(6, 1);
    fp1 = AtomPairs::getHashedTopologicalTorsionFingerprint(
        *m1, 1024, 4, (const std::vector<std::uint32_t> *)nullptr,
        (const std::vector<std::uint32_t> *)nullptr, &invars);
    fp2 = AtomPairs::getHashedTopologicalTorsionFingerprint(
        *m2, 1024, 4, (const std::vector<std::uint32_t> *)nullptr,
        (const std::vector<std::uint32_t> *)nullptr, &invars);
    TEST_ASSERT(*fp1 == *fp2);
    delete m1;
    delete m2;
    delete fp1;
    delete fp2;
  }
  {
    std::string smi = "C1=CC=CC=C1";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    smi = "C1=CC=CC=N1";
    RWMol *m2 = SmilesToMol(smi);
    TEST_ASSERT(m2);
    ExplicitBitVect *fp1 =
        AtomPairs::getHashedTopologicalTorsionFingerprintAsBitVect(*m1);
    ExplicitBitVect *fp2 =
        AtomPairs::getHashedTopologicalTorsionFingerprintAsBitVect(*m2);

    TEST_ASSERT(*fp1 != *fp2);
    delete fp1;
    delete fp2;

    UINT_VECT invars(6, 1);
    fp1 = AtomPairs::getHashedTopologicalTorsionFingerprintAsBitVect(
        *m1, 1024, 4, (const std::vector<std::uint32_t> *)nullptr,
        (const std::vector<std::uint32_t> *)nullptr, &invars);
    fp2 = AtomPairs::getHashedTopologicalTorsionFingerprintAsBitVect(
        *m2, 1024, 4, (const std::vector<std::uint32_t> *)nullptr,
        (const std::vector<std::uint32_t> *)nullptr, &invars);
    TEST_ASSERT(*fp1 == *fp2);
    delete m1;
    delete m2;
    delete fp1;
    delete fp2;
  }

  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void testRDKitFromAtoms() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdInfoLog)
      << "testing RDKit fingerprints rooted at particular atoms" << std::endl;
  {
    std::string smi = "CCCCCC";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    std::vector<std::uint32_t> fromAtoms;
    fromAtoms.push_back(0);
    ExplicitBitVect *fp1 = RDKFingerprintMol(*m1, 1, 4, 2048, 1, true, 0, 128,
                                             true, true, nullptr, &fromAtoms);
    TEST_ASSERT(fp1->getNumOnBits() == 4);
    delete m1;
    delete fp1;
  }
  {
    std::string smi = "CCCCCO";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    std::vector<std::uint32_t> fromAtoms;
    fromAtoms.push_back(0);
    fromAtoms.push_back(5);
    ExplicitBitVect *fp1 = RDKFingerprintMol(*m1, 1, 4, 2048, 1, true, 0, 128,
                                             true, true, nullptr, &fromAtoms);
    TEST_ASSERT(fp1->getNumOnBits() == 8);
    delete m1;
    delete fp1;
  }
  {
    std::string smi = "CCCCCO";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    std::vector<std::uint32_t> fromAtoms;
    fromAtoms.push_back(0);
    fromAtoms.push_back(5);
    ExplicitBitVect *fp1 = RDKFingerprintMol(*m1, 1, 4, 2048, 1, true, 0, 128,
                                             false, true, nullptr, &fromAtoms);
    TEST_ASSERT(fp1->getNumOnBits() == 8);
    delete m1;
    delete fp1;
  }
  {
    std::string smi = "CCCCCO";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    std::vector<std::uint32_t> fromAtoms;
    fromAtoms.push_back(0);
    ExplicitBitVect *fp1 = LayeredFingerprintMol(
        *m1, 0xFFFFFFFF, 1, 4, 2048, nullptr, nullptr, true, &fromAtoms);
    TEST_ASSERT(fp1->getNumOnBits() == 20);
    delete m1;
    delete fp1;
  }
  {
    std::string smi = "CCCCCO";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    std::vector<std::uint32_t> fromAtoms;
    fromAtoms.push_back(0);
    fromAtoms.push_back(5);
    ExplicitBitVect *fp1 = LayeredFingerprintMol(
        *m1, 0xFFFFFFFF, 1, 4, 2048, nullptr, nullptr, true, &fromAtoms);
    TEST_ASSERT(fp1->getNumOnBits() == 24);
    delete m1;
    delete fp1;
  }
  {
    std::string smi = "CCCCCO";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    std::vector<std::uint32_t> fromAtoms;
    fromAtoms.push_back(0);
    fromAtoms.push_back(5);
    ExplicitBitVect *fp1 = LayeredFingerprintMol(
        *m1, 0xFFFFFFFF, 1, 4, 2048, nullptr, nullptr, false, &fromAtoms);
    TEST_ASSERT(fp1->getNumOnBits() == 24);
    delete m1;
    delete fp1;
  }
  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void testMACCS() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdInfoLog) << "testing MACCS key calculation" << std::endl;
  {
    std::string smi = "CNO";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    ExplicitBitVect *fp1 = MACCSFingerprints::getFingerprintAsBitVect(*m1);
    TEST_ASSERT(fp1->getNumOnBits() == 15);
    unsigned int _onBits[] = {24,  68,  69,  71,  93,  94,  102, 124,
                              131, 139, 151, 158, 160, 161, 164};
    std::vector<unsigned int> onBits(
        _onBits, _onBits + sizeof(_onBits) / sizeof(*_onBits));
    for (auto ob : onBits) {
      TEST_ASSERT((*fp1)[ob]);
    }
    delete m1;
    delete fp1;
  }
  {
    std::string smi = "CCC";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    ExplicitBitVect *fp1 = MACCSFingerprints::getFingerprintAsBitVect(*m1);
    TEST_ASSERT(fp1->getNumOnBits() == 5);
    unsigned int _onBits[] = {74, 114, 149, 155, 160};
    std::vector<unsigned int> onBits(
        _onBits, _onBits + sizeof(_onBits) / sizeof(*_onBits));
    for (auto ob : onBits) {
      TEST_ASSERT((*fp1)[ob]);
    }
    delete m1;
    delete fp1;
  }
  {
    std::string smi = "CC.CO";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    ExplicitBitVect *fp1 = MACCSFingerprints::getFingerprintAsBitVect(*m1);
    TEST_ASSERT(fp1->getNumOnBits() == 8);
    unsigned int _onBits[] = {93, 139, 141, 149, 157, 160, 164, 166};
    std::vector<unsigned int> onBits(
        _onBits, _onBits + sizeof(_onBits) / sizeof(*_onBits));
    for (auto ob : onBits) {
      TEST_ASSERT((*fp1)[ob]);
    }
    delete m1;
    delete fp1;
  }
  {
    // check that bit 44 "OTHER" gets properly set:
    std::string smi = "CC[SeH]";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    ExplicitBitVect *fp1 = MACCSFingerprints::getFingerprintAsBitVect(*m1);
    TEST_ASSERT((*fp1)[44]);
    delete m1;
    delete fp1;
  }
  {
    // check bits 124 and 130 part 1
    std::string smi = "CNNCOOC";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    ExplicitBitVect *fp1 = MACCSFingerprints::getFingerprintAsBitVect(*m1);
    TEST_ASSERT((*fp1)[124]);
    TEST_ASSERT((*fp1)[130]);
    delete m1;
    delete fp1;
  }
  {
    // check bits 124 and 130 part 2
    std::string smi = "CNNCC";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    ExplicitBitVect *fp1 = MACCSFingerprints::getFingerprintAsBitVect(*m1);
    TEST_ASSERT((*fp1)[124]);
    TEST_ASSERT(!(*fp1)[130]);
    delete m1;
    delete fp1;
  }
  {
    // check bits 124 and 130 part 3
    std::string smi = "CNCCC";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    ExplicitBitVect *fp1 = MACCSFingerprints::getFingerprintAsBitVect(*m1);
    TEST_ASSERT(!(*fp1)[124]);
    TEST_ASSERT(!(*fp1)[130]);
    delete m1;
    delete fp1;
  }
  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void testRDKitAtomBits() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdInfoLog) << "testing RDKit fingerprints reporting atomBits"
                       << std::endl;
  {
    std::string smi = "CCCCCC";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    std::vector<std::vector<std::uint32_t>> atomBits(m1->getNumAtoms());
    ExplicitBitVect *fp1 =
        RDKFingerprintMol(*m1, 1, 4, 2048, 1, true, 0, 128, true, true, nullptr,
                          nullptr, &atomBits);
    TEST_ASSERT(fp1->getNumOnBits() == 4);
    for (unsigned int i = 0; i < m1->getNumAtoms(); ++i) {
      TEST_ASSERT(atomBits[i].size() == 4);
    }
    delete m1;
    delete fp1;
  }
  {
    std::string smi = "CCCO";
    RWMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    std::vector<std::vector<std::uint32_t>> atomBits(m1->getNumAtoms());
    ExplicitBitVect *fp1 =
        RDKFingerprintMol(*m1, 1, 2, 2048, 1, true, 0, 128, true, true, nullptr,
                          nullptr, &atomBits);
    TEST_ASSERT(fp1->getNumOnBits() == 4);
    TEST_ASSERT(atomBits[0].size() == 2);
    TEST_ASSERT(atomBits[1].size() == 3);
    TEST_ASSERT(atomBits[2].size() == 4);
    TEST_ASSERT(atomBits[3].size() == 2);
    delete m1;
    delete fp1;
  }
  BOOST_LOG(rdInfoLog) << "done" << std::endl;
}

void testChiralPairs() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test Atom Pairs including info about chirality."
                        << std::endl;

  ROMol *m1, *m2, *m3;

  m1 = SmilesToMol("CC[CH](F)Cl");
  TEST_ASSERT(m1);
  m2 = SmilesToMol("CC[C@H](F)Cl");
  TEST_ASSERT(m1);
  m3 = SmilesToMol("CC[C@@H](F)Cl");
  TEST_ASSERT(m1);

  {
    SparseIntVect<int> *fp1, *fp2, *fp3;
    fp1 = AtomPairs::getAtomPairFingerprint(*m1, 1, 5);
    TEST_ASSERT(fp1->getTotalVal() == 10);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 10);
    fp2 = AtomPairs::getAtomPairFingerprint(*m2, 1, 5);
    TEST_ASSERT(fp2->getTotalVal() == 10);
    TEST_ASSERT(fp2->getNonzeroElements().size() == 10);
    fp3 = AtomPairs::getAtomPairFingerprint(*m3, 1, 5);
    TEST_ASSERT(fp3->getTotalVal() == 10);
    TEST_ASSERT(fp3->getNonzeroElements().size() == 10);

    TEST_ASSERT((*fp1) == (*fp2));
    TEST_ASSERT((*fp1) == (*fp3));
    TEST_ASSERT((*fp2) == (*fp3));

    delete fp1;
    delete fp2;
    delete fp3;

    fp1 = AtomPairs::getAtomPairFingerprint(*m1, 1, 5, nullptr, nullptr,
                                            nullptr, true);
    TEST_ASSERT(fp1->getTotalVal() == 10);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 10);
    fp2 = AtomPairs::getAtomPairFingerprint(*m2, 1, 5, nullptr, nullptr,
                                            nullptr, true);
    TEST_ASSERT(fp2->getTotalVal() == 10);
    TEST_ASSERT(fp2->getNonzeroElements().size() == 10);
    fp3 = AtomPairs::getAtomPairFingerprint(*m3, 1, 5, nullptr, nullptr,
                                            nullptr, true);
    TEST_ASSERT(fp3->getTotalVal() == 10);
    TEST_ASSERT(fp3->getNonzeroElements().size() == 10);

    TEST_ASSERT((*fp1) != (*fp2));
    TEST_ASSERT((*fp1) != (*fp3));
    TEST_ASSERT((*fp2) != (*fp3));

    delete fp1;
    delete fp2;
    delete fp3;
  }

  {
    SparseIntVect<int> *fp1, *fp2, *fp3;
    fp1 = AtomPairs::getHashedAtomPairFingerprint(*m1, 4096, 1, 5);
    TEST_ASSERT(fp1->getTotalVal() == 10);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 10);
    fp2 = AtomPairs::getHashedAtomPairFingerprint(*m2, 4096, 1, 5);
    TEST_ASSERT(fp2->getTotalVal() == 10);
    TEST_ASSERT(fp2->getNonzeroElements().size() == 10);
    fp3 = AtomPairs::getHashedAtomPairFingerprint(*m3, 4096, 1, 5);
    TEST_ASSERT(fp3->getTotalVal() == 10);
    TEST_ASSERT(fp3->getNonzeroElements().size() == 10);

    TEST_ASSERT((*fp1) == (*fp2));
    TEST_ASSERT((*fp1) == (*fp3));
    TEST_ASSERT((*fp2) == (*fp3));

    delete fp1;
    delete fp2;
    delete fp3;

    fp1 = AtomPairs::getHashedAtomPairFingerprint(*m1, 4096, 1, 5, nullptr,
                                                  nullptr, nullptr, true);
    TEST_ASSERT(fp1->getTotalVal() == 10);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 10);
    fp2 = AtomPairs::getHashedAtomPairFingerprint(*m2, 4096, 1, 5, nullptr,
                                                  nullptr, nullptr, true);
    TEST_ASSERT(fp2->getTotalVal() == 10);
    TEST_ASSERT(fp2->getNonzeroElements().size() == 10);
    fp3 = AtomPairs::getHashedAtomPairFingerprint(*m3, 4096, 1, 5, nullptr,
                                                  nullptr, nullptr, true);
    TEST_ASSERT(fp3->getTotalVal() == 10);
    TEST_ASSERT(fp3->getNonzeroElements().size() == 10);

    TEST_ASSERT((*fp1) != (*fp2));
    TEST_ASSERT((*fp1) != (*fp3));
    TEST_ASSERT((*fp2) != (*fp3));

    delete fp1;
    delete fp2;
    delete fp3;
  }

  delete m1;
  delete m2;
  delete m3;
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}
void testChiralTorsions() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog)
      << "    Test Topological Torsions including info about chirality."
      << std::endl;

  ROMol *m1, *m2, *m3;

  m1 = SmilesToMol("CC[CH](F)Cl");
  TEST_ASSERT(m1);
  m2 = SmilesToMol("CC[C@H](F)Cl");
  TEST_ASSERT(m1);
  m3 = SmilesToMol("CC[C@@H](F)Cl");
  TEST_ASSERT(m1);

  {
    SparseIntVect<boost::int64_t> *fp1, *fp2, *fp3;
    fp1 = AtomPairs::getTopologicalTorsionFingerprint(*m1);
    TEST_ASSERT(fp1->getTotalVal() == 2);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 2);
    fp2 = AtomPairs::getTopologicalTorsionFingerprint(*m2);
    TEST_ASSERT(fp2->getTotalVal() == 2);
    TEST_ASSERT(fp2->getNonzeroElements().size() == 2);
    fp3 = AtomPairs::getTopologicalTorsionFingerprint(*m3);
    TEST_ASSERT(fp3->getTotalVal() == 2);
    TEST_ASSERT(fp3->getNonzeroElements().size() == 2);

    TEST_ASSERT((*fp1) == (*fp2));
    TEST_ASSERT((*fp1) == (*fp3));
    TEST_ASSERT((*fp2) == (*fp3));

    delete fp1;
    delete fp2;
    delete fp3;

    fp1 = AtomPairs::getTopologicalTorsionFingerprint(*m1, 4, nullptr, nullptr,
                                                      nullptr, true);
    TEST_ASSERT(fp1->getTotalVal() == 2);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 2);
    fp2 = AtomPairs::getTopologicalTorsionFingerprint(*m2, 4, nullptr, nullptr,
                                                      nullptr, true);
    TEST_ASSERT(fp2->getTotalVal() == 2);
    TEST_ASSERT(fp2->getNonzeroElements().size() == 2);
    fp3 = AtomPairs::getTopologicalTorsionFingerprint(*m3, 4, nullptr, nullptr,
                                                      nullptr, true);
    TEST_ASSERT(fp3->getTotalVal() == 2);
    TEST_ASSERT(fp3->getNonzeroElements().size() == 2);

    TEST_ASSERT((*fp1) != (*fp2));
    TEST_ASSERT((*fp1) != (*fp3));
    TEST_ASSERT((*fp2) != (*fp3));

    delete fp1;
    delete fp2;
    delete fp3;
  }

  {
    SparseIntVect<boost::int64_t> *fp1, *fp2, *fp3;
    fp1 = AtomPairs::getHashedTopologicalTorsionFingerprint(*m1, 4096);
    TEST_ASSERT(fp1->getTotalVal() == 2);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 2);
    fp2 = AtomPairs::getHashedTopologicalTorsionFingerprint(*m2, 4096);
    TEST_ASSERT(fp2->getTotalVal() == 2);
    TEST_ASSERT(fp2->getNonzeroElements().size() == 2);
    fp3 = AtomPairs::getHashedTopologicalTorsionFingerprint(*m3, 4096);
    TEST_ASSERT(fp3->getTotalVal() == 2);
    TEST_ASSERT(fp3->getNonzeroElements().size() == 2);

    TEST_ASSERT((*fp1) == (*fp2));
    TEST_ASSERT((*fp1) == (*fp3));
    TEST_ASSERT((*fp2) == (*fp3));

    delete fp1;
    delete fp2;
    delete fp3;

    fp1 = AtomPairs::getHashedTopologicalTorsionFingerprint(
        *m1, 4096, 4, nullptr, nullptr, nullptr, true);
    TEST_ASSERT(fp1->getTotalVal() == 2);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 2);
    fp2 = AtomPairs::getHashedTopologicalTorsionFingerprint(
        *m2, 4096, 4, nullptr, nullptr, nullptr, true);
    TEST_ASSERT(fp2->getTotalVal() == 2);
    TEST_ASSERT(fp2->getNonzeroElements().size() == 2);
    fp3 = AtomPairs::getHashedTopologicalTorsionFingerprint(
        *m3, 4096, 4, nullptr, nullptr, nullptr, true);
    TEST_ASSERT(fp3->getTotalVal() == 2);
    TEST_ASSERT(fp3->getNonzeroElements().size() == 2);

    TEST_ASSERT((*fp1) != (*fp2));
    TEST_ASSERT((*fp1) != (*fp3));
    TEST_ASSERT((*fp2) != (*fp3));

    delete fp1;
    delete fp2;
    delete fp3;
  }

  delete m1;
  delete m2;
  delete m3;
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue25() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog)
      << "    Test GitHub Issue 25: fingerprint backwards compatibility."
      << std::endl;

  {
    ROMol *m1 = SmilesToMol("CCCCO");
    TEST_ASSERT(m1);
    SparseIntVect<boost::int64_t> *fp1;
    fp1 = AtomPairs::getTopologicalTorsionFingerprint(*m1);
    TEST_ASSERT(fp1);
    TEST_ASSERT(fp1->getTotalVal() == 2);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 2);
    TEST_ASSERT((*fp1)[4437590048LL] == 1);
    TEST_ASSERT((*fp1)[12893306913LL] == 1);
    delete fp1;
    delete m1;
  }
  {
    ROMol *m1 = SmilesToMol("CCCCO");
    TEST_ASSERT(m1);
    SparseIntVect<boost::int64_t> *fp1;
    fp1 = AtomPairs::getHashedTopologicalTorsionFingerprint(*m1, 1000);
    TEST_ASSERT(fp1);
    TEST_ASSERT(fp1->getTotalVal() == 2);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 2);
    TEST_ASSERT((*fp1)[24] == 1);
    TEST_ASSERT((*fp1)[288] == 1);
    delete fp1;
    delete m1;
  }
  {
    ROMol *m1 = SmilesToMol("CCO");
    TEST_ASSERT(m1);
    SparseIntVect<std::int32_t> *fp1;
    fp1 = AtomPairs::getAtomPairFingerprint(*m1);
    TEST_ASSERT(fp1);
    TEST_ASSERT(fp1->getTotalVal() == 3);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 3);
    TEST_ASSERT((*fp1)[558113] == 1);
    TEST_ASSERT((*fp1)[1590306] == 1);
    TEST_ASSERT((*fp1)[1590337] == 1);
    delete fp1;
    delete m1;
  }
  {
    ROMol *m1 = SmilesToMol("CCO");
    TEST_ASSERT(m1);
    SparseIntVect<std::int32_t> *fp1;
    fp1 = AtomPairs::getHashedAtomPairFingerprint(*m1);
    TEST_ASSERT(fp1);
    TEST_ASSERT(fp1->getTotalVal() == 3);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 3);
    TEST_ASSERT((*fp1)[1375] == 1);
    TEST_ASSERT((*fp1)[1423] == 1);
    TEST_ASSERT((*fp1)[1503] == 1);
    delete fp1;
    delete m1;
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue151() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog)
      << "    Test GitHub Issue 151: PatternFingerprint problems" << std::endl;

  {
    ROMol *qm = SmilesToMol("CCCn1c2ccccc2c2ccccc21");
    TEST_ASSERT(qm);
    ROMol *m =
        SmilesToMol("O=C1NCc2c1c1c3cc(Br)ccc3n3c1c1c2c2ccccc2n1CC(CO)C3");
    TEST_ASSERT(m);
    ExplicitBitVect *qbv = PatternFingerprintMol(*qm, 2048);
    ExplicitBitVect *mbv = PatternFingerprintMol(*m, 2048);
    MatchVectType mv;
    TEST_ASSERT(SubstructMatch(*m, *qm, mv));
    TEST_ASSERT(AllProbeBitsMatch(*qbv, *mbv));

    delete qbv;
    delete mbv;
    delete qm;
    delete m;
  }
  {
    ROMol *qm = SmilesToMol("c1ccc2c(c1)[nH]c1ccccc12");
    TEST_ASSERT(qm);
    ROMol *m =
        SmilesToMol("O=C1NCc2c1c1c3cc(Br)ccc3n3c1c1c2c2ccccc2n1CC(CO)C3");
    TEST_ASSERT(m);
    ExplicitBitVect *qbv = PatternFingerprintMol(*qm, 2048);
    ExplicitBitVect *mbv = PatternFingerprintMol(*m, 2048);
    MatchVectType mv;
    TEST_ASSERT(SubstructMatch(*m, *qm, mv));
    TEST_ASSERT(AllProbeBitsMatch(*qbv, *mbv));

    delete qbv;
    delete mbv;
    delete qm;
    delete m;
  }
  {
    ROMol *qm = SmilesToMol("CC(C)c1nnc(N)[nH]1");
    TEST_ASSERT(qm);
    ROMol *m = SmilesToMol("CC(C)c1nc2NCCCn2n1");
    TEST_ASSERT(m);
    ExplicitBitVect *qbv = PatternFingerprintMol(*qm, 2048);
    ExplicitBitVect *mbv = PatternFingerprintMol(*m, 2048);
    MatchVectType mv;
    TEST_ASSERT(SubstructMatch(*m, *qm, mv));
    TEST_ASSERT(AllProbeBitsMatch(*qbv, *mbv));

    delete qbv;
    delete mbv;
    delete qm;
    delete m;
  }
  {
    ROMol *qm = SmilesToMol("CC(C)c1nnc(N)[nH]1");
    TEST_ASSERT(qm);
    ROMol *m = SmilesToMol(
        "CN1c2nc(C3CCN(S(=O)(=O)c4ccc(Cl)cc4Cl)CC3)nn2S(=O)(=O)c2ccccc21");
    TEST_ASSERT(m);
    ExplicitBitVect *qbv = PatternFingerprintMol(*qm, 2048);
    ExplicitBitVect *mbv = PatternFingerprintMol(*m, 2048);
    MatchVectType mv;
    TEST_ASSERT(SubstructMatch(*m, *qm, mv));
    TEST_ASSERT(AllProbeBitsMatch(*qbv, *mbv));

    delete qbv;
    delete mbv;
    delete qm;
    delete m;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void test3DAtomPairs() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test 3D atom pairs." << std::endl;

  std::string fName = getenv("RDBASE");
  fName += "/Code/GraphMol/Fingerprints/testData/triangle.sdf";
  SDMolSupplier suppl(fName);
  {
    ROMol *mol = suppl.next();
    SparseIntVect<std::int32_t> *fp;
    // do the 3D version
    fp = AtomPairs::getHashedAtomPairFingerprint(
        *mol, 2048, 1, AtomPairs::maxPathLen - 1, nullptr, nullptr, nullptr,
        false, false);
    TEST_ASSERT(fp->getTotalVal() == 3);
    TEST_ASSERT(fp->getNonzeroElements().size() == 1);
    delete fp;
    // now do the 2D version
    fp = AtomPairs::getHashedAtomPairFingerprint(
        *mol, 2048, 1, AtomPairs::maxPathLen - 1, nullptr, nullptr, nullptr,
        false, true);
    TEST_ASSERT(fp->getTotalVal() == 3);
    TEST_ASSERT(fp->getNonzeroElements().size() == 1);
    delete fp;
    fp = nullptr;

    // we should get a conformer exception if there are no conformers:
    mol->clearConformers();
    bool ok = false;
    try {
      fp = AtomPairs::getHashedAtomPairFingerprint(
          *mol, 2048, 1, AtomPairs::maxPathLen - 1, nullptr, nullptr, nullptr,
          false, false);
    } catch (ConformerException &) {
      ok = true;
    }
    TEST_ASSERT(ok);
    if (fp != nullptr) {
      delete fp;
    }
    delete mol;
  }
  {
    ROMol *mol = suppl.next();
    SparseIntVect<std::int32_t> *fp;
    // do the 3D version
    fp = AtomPairs::getHashedAtomPairFingerprint(
        *mol, 2048, 1, AtomPairs::maxPathLen - 1, nullptr, nullptr, nullptr,
        false, false);
    TEST_ASSERT(fp->getTotalVal() == 3);
    TEST_ASSERT(fp->getNonzeroElements().size() == 2);
    delete fp;
    // now do the 2D version
    fp = AtomPairs::getHashedAtomPairFingerprint(
        *mol, 2048, 1, AtomPairs::maxPathLen - 1, nullptr, nullptr, nullptr,
        false, true);
    TEST_ASSERT(fp->getTotalVal() == 3);
    TEST_ASSERT(fp->getNonzeroElements().size() == 1);
    delete fp;
    delete mol;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue195() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test GitHub Issue 195: GenMACCSKeys() raises "
                           "an exception with an empty molecule"
                        << std::endl;

  {
    auto *m1 = new ROMol();
    ExplicitBitVect *fp1 = MACCSFingerprints::getFingerprintAsBitVect(*m1);
    TEST_ASSERT(fp1->getNumOnBits() == 0);
    delete fp1;
    delete m1;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue258() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog)
      << "    Test GitHub Issue 258: Bad pattern fingerprint for query molecule"
      << std::endl;

  {
    ROMol *qm = SmartsToMol("n2c(-[#6])ccc2-[#6]", 0, true);
    TEST_ASSERT(qm);
    ROMol *m = SmilesToMol("Clc1c(cccc1)-n2c(c(cc2C)C=NNC(=O)CSc3ncccn3)C");
    TEST_ASSERT(m);

    ExplicitBitVect *qbv = PatternFingerprintMol(*qm, 2048);
    ExplicitBitVect *mbv = PatternFingerprintMol(*m, 2048);
    MatchVectType mv;
    TEST_ASSERT(SubstructMatch(*m, *qm, mv));
    TEST_ASSERT(AllProbeBitsMatch(*qbv, *mbv));

    delete qm;
    delete m;
    delete qbv;
    delete mbv;
  }
  {
    ROMol *qm = SmartsToMol("n2c(cc(c2-[#6]))-[#6]", 0, true);
    TEST_ASSERT(qm);
    ROMol *m = SmilesToMol("Clc1c(cccc1)-n2c(c(cc2C)C=NNC(=O)CSc3ncccn3)C");
    TEST_ASSERT(m);

    ExplicitBitVect *qbv = PatternFingerprintMol(*qm, 2048);
    ExplicitBitVect *mbv = PatternFingerprintMol(*m, 2048);
    MatchVectType mv;
    TEST_ASSERT(SubstructMatch(*m, *qm, mv));
    TEST_ASSERT(AllProbeBitsMatch(*qbv, *mbv));

    delete qm;
    delete m;
    delete qbv;
    delete mbv;
  }
  {
    ROMol *qm = SmartsToMol(
        "n2(-[#6]:1:[!#1]:[#6]:[#6]:[#6]:[#6]:1)c(cc(c2-[#6;X4]))-[#6;X4]", 0,
        true);
    TEST_ASSERT(qm);
    ROMol *m = SmilesToMol("n2(-c:1:c:c:c:c:c:1)c(cc(c2-C))-C", 0, true);
    TEST_ASSERT(m);

    ExplicitBitVect *qbv = PatternFingerprintMol(*qm, 2048);
    ExplicitBitVect *mbv = PatternFingerprintMol(*m, 2048);

#if 0
    ExplicitBitVect dv=(*qbv)^((*qbv)&(*mbv));
    IntVect iv;
    dv.getOnBits(iv);
    std::cerr<<"\n\n";
    std::copy(iv.begin(),iv.end(),std::ostream_iterator<int>(std::cerr,", "));
    std::cerr<<std::endl;
#endif
    MatchVectType mv;
    TEST_ASSERT(SubstructMatch(*m, *qm, mv));
    TEST_ASSERT(AllProbeBitsMatch(*qbv, *mbv));

    delete qm;
    delete m;
    delete qbv;
    delete mbv;
  }
  {
    ROMol *qm = SmartsToMol(
        "n2(-[#6]:1:[!#1]:[#6]:[#6]:[#6]:[#6]:1)c(cc(c2-[#6;X4]))-[#6;X4]", 0,
        true);
    TEST_ASSERT(qm);
    ROMol *m = SmilesToMol("Clc1c(cccc1)-n2c(c(cc2C)C=NNC(=O)CSc3ncccn3)C");
    TEST_ASSERT(m);

    ExplicitBitVect *qbv = PatternFingerprintMol(*qm, 2048);
    ExplicitBitVect *mbv = PatternFingerprintMol(*m, 2048);

    MatchVectType mv;
    TEST_ASSERT(SubstructMatch(*m, *qm, mv));
    TEST_ASSERT(AllProbeBitsMatch(*qbv, *mbv));

    delete qm;
    delete m;
    delete qbv;
    delete mbv;
  }
  {
    ROMol *qm = SmartsToMol(
        "n2(-[#6]:1:[!#1]:[#6]:[#6]:[#6]:[#6]:1)c(cc(c2-[#6;X4])-[#1])-[#6;X4]",
        0, true);
    TEST_ASSERT(qm);
    ROMol *m = SmilesToMol("Clc1c(cccc1)-n2c(c(cc2C)C=NNC(=O)CSc3ncccn3)C");
    TEST_ASSERT(m);

    ExplicitBitVect *qbv = PatternFingerprintMol(*qm, 2048);
    ExplicitBitVect *mbv = PatternFingerprintMol(*m, 2048);
    MatchVectType mv;
    TEST_ASSERT(SubstructMatch(*m, *qm, mv));
    TEST_ASSERT(AllProbeBitsMatch(*qbv, *mbv));

    delete qm;
    delete m;
    delete qbv;
    delete mbv;
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

#ifdef RDK_TEST_MULTITHREADED
namespace {
void runblock(const std::vector<ROMol *> &mols, unsigned int count,
              unsigned int idx,
              const std::vector<ExplicitBitVect *> &referenceData,
              unsigned int nReps) {
  for (unsigned int j = 0; j < nReps; j++) {
    for (unsigned int i = 0; i < mols.size(); ++i) {
      if (i % count != idx) {
        continue;
      }
      ROMol *mol = mols[i];
      ExplicitBitVect *lbv = PatternFingerprintMol(*mol, 2048);
      if (referenceData.size() && referenceData[i]) {
        TEST_ASSERT((*lbv) == (*referenceData[i]));
      }
      delete lbv;
    }
  }
};
}  // namespace
#include <thread>
#include <future>
void testMultithreadedPatternFP() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test multithreading with the pattern FP"
                        << std::endl;

  std::string fName = getenv("RDBASE");
  fName += "/Data/NCI/first_200.props.sdf";
  SDMolSupplier suppl(fName);
  std::cerr << "reading molecules" << std::endl;
  std::vector<ROMol *> mols;
  std::vector<ExplicitBitVect *> referenceData;
  while (!suppl.atEnd() && mols.size() < 100) {
    ROMol *mol = nullptr;
    try {
      mol = suppl.next();
    } catch (...) {
      continue;
    }
    if (!mol) {
      continue;
    }
    mols.push_back(mol);
  }
  std::vector<std::future<void>> tg;

  std::cerr << "pass 1" << std::endl;
  unsigned int count = 4;
  for (unsigned int i = 0; i < count; ++i) {
    std::cerr << " launch :" << i << std::endl;
    std::cerr.flush();
    tg.emplace_back(std::async(std::launch::async, runblock, mols, count, i,
                               referenceData, 10));
  }
  for (auto &fut : tg) {
    fut.get();
  }
  tg.clear();

  for (const auto *mol : mols) {
    ExplicitBitVect *bv = PatternFingerprintMol(*mol, 2048);
    referenceData.push_back(bv);
  }
  std::cerr << "pass 2" << std::endl;
  for (unsigned int i = 0; i < count; ++i) {
    std::cerr << " launch :" << i << std::endl;
    std::cerr.flush();
    tg.emplace_back(std::async(std::launch::async, runblock, mols, count, i,
                               referenceData, 300));
  }
  for (auto &fut : tg) {
    fut.get();
  }

  for (unsigned int i = 0; i < mols.size(); ++i) {
    delete mols[i];
    delete referenceData[i];
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}
#else
void testMultithreadedPatternFP() {}
#endif

void testGitHubIssue334() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test GitHub Issue 334: explicit Hs in SMILES "
                           "modifies atom pair (and topological torsion) FP."
                        << std::endl;

  {
    ROMol *m1 = SmilesToMol("N#C");
    TEST_ASSERT(m1);
    SparseIntVect<std::int32_t> *fp1;
    fp1 = AtomPairs::getAtomPairFingerprint(*m1);
    TEST_ASSERT(fp1);
    delete m1;

    m1 = SmilesToMol("N#[CH]");
    SparseIntVect<std::int32_t> *fp2;
    fp2 = AtomPairs::getAtomPairFingerprint(*m1);
    TEST_ASSERT(fp2);
    delete m1;

    TEST_ASSERT(fp1->getTotalVal() == fp2->getTotalVal());
    TEST_ASSERT(fp1->getNonzeroElements().size() ==
                fp2->getNonzeroElements().size());
    TEST_ASSERT(*fp1 == *fp2);
    delete fp1;
    delete fp2;
  }
  {
    ROMol *m1 = SmilesToMol("N#C");
    TEST_ASSERT(m1);
    SparseIntVect<boost::int64_t> *fp1;
    fp1 = AtomPairs::getTopologicalTorsionFingerprint(*m1);
    TEST_ASSERT(fp1);
    delete m1;

    m1 = SmilesToMol("N#[CH]");
    SparseIntVect<boost::int64_t> *fp2;
    fp2 = AtomPairs::getTopologicalTorsionFingerprint(*m1);
    TEST_ASSERT(fp2);
    delete m1;

    TEST_ASSERT(fp1->getTotalVal() == fp2->getTotalVal());
    TEST_ASSERT(fp1->getNonzeroElements().size() ==
                fp2->getNonzeroElements().size());
    TEST_ASSERT(*fp1 == *fp2);
    delete fp1;
    delete fp2;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue695() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test GitHub Issue 695: Include cis/trans "
                           "stereochemistry when useChirality=true with the "
                           "morgan fingerprints"
                        << std::endl;

  {
    ROMol *m1 = SmilesToMol("CC=CC");
    TEST_ASSERT(m1);
    SparseIntVect<std::uint32_t> *fp;
    SparseIntVect<std::uint32_t>::StorageType::const_iterator iter;

    fp = MorganFingerprints::getFingerprint(*m1, 1, nullptr, nullptr, false);
    TEST_ASSERT(fp);
    TEST_ASSERT(fp->getNonzeroElements().size() == 4);
    iter = fp->getNonzeroElements().find(736731344);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(2246703798);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(2246728737);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(3545353036);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    delete fp;

    fp = MorganFingerprints::getFingerprint(*m1, 1, nullptr, nullptr, true);
    TEST_ASSERT(fp);
    TEST_ASSERT(fp->getNonzeroElements().size() == 4);
    iter = fp->getNonzeroElements().find(736731344);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(2246703798);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(2246728737);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(3545353036);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);

    delete fp;

    delete m1;
  }
  {
    ROMol *m1 = SmilesToMol("C/C=C/C");
    TEST_ASSERT(m1);
    SparseIntVect<std::uint32_t> *fp;
    SparseIntVect<std::uint32_t>::StorageType::const_iterator iter;

    fp = MorganFingerprints::getFingerprint(*m1, 1, nullptr, nullptr, false);
    TEST_ASSERT(fp);
    TEST_ASSERT(fp->getNonzeroElements().size() == 4);
    iter = fp->getNonzeroElements().find(736731344);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(2246703798);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(2246728737);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(3545353036);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    delete fp;

    fp = MorganFingerprints::getFingerprint(*m1, 1, nullptr, nullptr, true);
    TEST_ASSERT(fp);
    TEST_ASSERT(fp->getNonzeroElements().size() == 4);

#if 0
    for (iter = fp->getNonzeroElements().begin();
         iter != fp->getNonzeroElements().end(); ++iter) {
      std::cerr << "   " << iter->first << ": " << iter->second << std::endl;
    }
    std::cerr << "  ------------ " << std::endl;
#endif

    iter = fp->getNonzeroElements().find(736735794);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(2246703798);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(2246728737);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(3545353036);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    delete fp;

    delete m1;
  }
  {
    ROMol *m1 = SmilesToMol("C/C=C\\C");
    TEST_ASSERT(m1);
    SparseIntVect<std::uint32_t> *fp;
    SparseIntVect<std::uint32_t>::StorageType::const_iterator iter;

    fp = MorganFingerprints::getFingerprint(*m1, 1, nullptr, nullptr, false);
    TEST_ASSERT(fp);
    TEST_ASSERT(fp->getNonzeroElements().size() == 4);
    iter = fp->getNonzeroElements().find(736731344);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(2246703798);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(2246728737);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(3545353036);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    delete fp;

    fp = MorganFingerprints::getFingerprint(*m1, 1, nullptr, nullptr, true);
#if 0
    for (iter = fp->getNonzeroElements().begin();
         iter != fp->getNonzeroElements().end(); ++iter) {
      std::cerr << "   " << iter->first << ": " << iter->second << std::endl;
    }
    std::cerr << "  ------------ " << std::endl;
#endif
    TEST_ASSERT(fp);
    TEST_ASSERT(fp->getNonzeroElements().size() == 4);
    iter = fp->getNonzeroElements().find(736735858);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(2246703798);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(2246728737);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    iter = fp->getNonzeroElements().find(3545353036);
    TEST_ASSERT(iter != fp->getNonzeroElements().end() && iter->second == 2);
    delete fp;

    delete m1;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue811() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test GitHub Issue 811: rooted atom fingerprint "
                           "non identical for the same molecules #811"
                        << std::endl;
  {
    std::string dirName = getenv("RDBASE");
    dirName += "/Code/GraphMol/Fingerprints/testData/";

    ROMol *m1 = MolFileToMol(dirName + "github811a.mol");
    TEST_ASSERT(m1);
    ROMol *m2 = MolFileToMol(dirName + "github811b.mol");
    TEST_ASSERT(m2);

    SparseIntVect<boost::int64_t> *fp1, *fp2;

    std::vector<std::uint32_t> roots;
    roots.push_back(1);

    fp1 = AtomPairs::getTopologicalTorsionFingerprint(*m1, 7, &roots);
    SparseIntVect<boost::int64_t>::StorageType nz1 = fp1->getNonzeroElements();
    TEST_ASSERT(nz1.size() == 4);
    fp2 = AtomPairs::getTopologicalTorsionFingerprint(*m2, 7, &roots);
    SparseIntVect<boost::int64_t>::StorageType nz2 = fp2->getNonzeroElements();
    TEST_ASSERT(nz2.size() == 4);

    TEST_ASSERT(*fp1 == *fp2);

    delete fp1;
    delete fp2;
    delete m1;
    delete m2;
  }
  {
    ROMol *m1 = SmilesToMol("C1CC1");
    TEST_ASSERT(m1);

    SparseIntVect<boost::int64_t> *fp1;

    fp1 = AtomPairs::getTopologicalTorsionFingerprint(*m1);
    SparseIntVect<boost::int64_t>::StorageType nz1 = fp1->getNonzeroElements();
    TEST_ASSERT(nz1.size() == 1);
    delete fp1;
    delete m1;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testRDKFPUnfolded() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test unfolded version of RDKFP   " << std::endl;
  {
    ROMol *m1 = SmilesToMol("c1ccccc1N");
    TEST_ASSERT(m1);
    SparseIntVect<boost::uint64_t> *fp1;
    SparseIntVect<boost::uint64_t>::StorageType::const_iterator iter;

    fp1 = getUnfoldedRDKFingerprintMol(*m1);
    TEST_ASSERT(fp1);
#if 0
    for (iter = fp1->getNonzeroElements().begin();
         iter != fp1->getNonzeroElements().end(); ++iter) {
      std::cerr << "   " << iter->first << ": " << iter->second << std::endl;
    }
    std::cerr << "  ------------ " << std::endl;
#endif
    TEST_ASSERT(fp1->getNonzeroElements().size() == 19);
    iter = fp1->getNonzeroElements().find(374073638);
    TEST_ASSERT(iter != fp1->getNonzeroElements().end() && iter->second == 6);
    iter = fp1->getNonzeroElements().find(464351883);
    TEST_ASSERT(iter != fp1->getNonzeroElements().end() && iter->second == 2);
    iter = fp1->getNonzeroElements().find(1949583554);
    TEST_ASSERT(iter != fp1->getNonzeroElements().end() && iter->second == 6);
    iter = fp1->getNonzeroElements().find(4105342207);
    TEST_ASSERT(iter != fp1->getNonzeroElements().end() && iter->second == 1);
    iter = fp1->getNonzeroElements().find(794080973);
    TEST_ASSERT(iter != fp1->getNonzeroElements().end() && iter->second == 1);
    iter = fp1->getNonzeroElements().find(3826517238);
    TEST_ASSERT(iter != fp1->getNonzeroElements().end() && iter->second == 2);
    delete fp1;
    delete m1;
  }
  {
    ROMol *m1 = SmilesToMol("Cl");
    TEST_ASSERT(m1);
    SparseIntVect<boost::uint64_t> *fp1;
    SparseIntVect<boost::uint64_t>::StorageType::const_iterator iter;

    fp1 = getUnfoldedRDKFingerprintMol(*m1);
    TEST_ASSERT(fp1);
    TEST_ASSERT(fp1->getNonzeroElements().size() == 0);
    delete fp1;
    delete m1;
  }
  {
    ROMol *m1 = SmilesToMol("CCCO");
    TEST_ASSERT(m1);
    SparseIntVect<boost::uint64_t> *fp1;
    SparseIntVect<boost::uint64_t>::StorageType::const_iterator iter;
    std::map<boost::uint64_t, std::vector<std::vector<int>>> bitInfo;
    std::map<boost::uint64_t, std::vector<std::vector<int>>>::const_iterator
        iter2;

    fp1 = getUnfoldedRDKFingerprintMol(*m1, 1, 7, true, true, true, nullptr,
                                       nullptr, nullptr, &bitInfo);
    TEST_ASSERT(fp1);

#if 0
    for (iter = fp1->getNonzeroElements().begin();
         iter != fp1->getNonzeroElements().end(); ++iter) {
      std::cerr << "   " << iter->first << ": " << iter->second << std::endl;
    }
    std::cerr << "  ------------ " << std::endl;
#endif
#if 0
    for (iter2 = bitInfo.begin();
         iter2 != bitInfo.end(); ++iter2) {
      std::cerr << "   " << iter2->first << ": ";
      for (unsigned i=0; i<iter2->second.size(); i++){
        std::cerr << " [ ";
        for (unsigned j=0; j<iter2->second.at(i).size(); j++){
          std::cerr << iter2->second.at(i).at(j) << " ";
        }
        std::cerr << "], ";
      }
      std::cerr << std::endl;
    }
    std::cerr << "  ------------ " << std::endl;
#endif

    TEST_ASSERT(fp1->getNonzeroElements().size() == 5);
    iter = fp1->getNonzeroElements().find(1524090560);
    TEST_ASSERT(iter != fp1->getNonzeroElements().end() && iter->second == 1);
    iter = fp1->getNonzeroElements().find(1940446997);
    TEST_ASSERT(iter != fp1->getNonzeroElements().end() && iter->second == 1);
    iter = fp1->getNonzeroElements().find(3977409745);
    TEST_ASSERT(iter != fp1->getNonzeroElements().end() && iter->second == 1);
    iter = fp1->getNonzeroElements().find(4274652475);
    TEST_ASSERT(iter != fp1->getNonzeroElements().end() && iter->second == 1);
    iter = fp1->getNonzeroElements().find(4275705116);
    TEST_ASSERT(iter != fp1->getNonzeroElements().end() && iter->second == 2);

    iter2 = bitInfo.find(4275705116);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0][0] == 0);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second.size() == 2 &&
                iter2->second[1][0] == 1);
    iter2 = bitInfo.find(4274652475);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0][0] == 2);
    iter2 = bitInfo.find(3977409745);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0].size() == 3 &&
                iter2->second[0][0] == 0);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0].size() == 3 &&
                iter2->second[0][1] == 1);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0].size() == 3 &&
                iter2->second[0][2] == 2);
    iter2 = bitInfo.find(1524090560);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0].size() == 2 &&
                iter2->second[0][0] == 1);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0].size() == 2 &&
                iter2->second[0][1] == 2);
    delete fp1;
    delete m1;
  }
}

void testRDKFPBitInfo() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test bitinfo of RDKFP   " << std::endl;

  {
    ROMol *m1 = SmilesToMol("CCCO");
    TEST_ASSERT(m1);
    ExplicitBitVect *fp1;
    std::map<std::uint32_t, std::vector<std::vector<int>>> bitInfo;
    std::map<std::uint32_t, std::vector<std::vector<int>>>::const_iterator
        iter2;

    fp1 = RDKFingerprintMol(*m1, 1, 7, 2048, 2, true, 0.0, 128, true, true,
                            nullptr, nullptr, nullptr, &bitInfo);
    TEST_ASSERT(fp1);

#if 0
    for (iter2 = bitInfo.begin();
         iter2 != bitInfo.end(); ++iter2) {
      std::cerr << "   " << iter2->first << ": ";
      for (unsigned i=0; i<iter2->second.size(); i++){
        std::cerr << " [ ";
        for (unsigned j=0; j<iter2->second.at(i).size(); j++){
          std::cerr << iter2->second.at(i).at(j) << " ";
        }
        std::cerr << "], ";
      }
      std::cerr << std::endl;
    }
    std::cerr << "  ------------ " << std::endl;
#endif

    iter2 = bitInfo.find(1772);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0][0] == 0);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second.size() == 2 &&
                iter2->second[1][0] == 1);
    iter2 = bitInfo.find(562);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0][0] == 2);
    iter2 = bitInfo.find(1118);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0].size() == 3 &&
                iter2->second[0][0] == 0);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0].size() == 3 &&
                iter2->second[0][1] == 1);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0].size() == 3 &&
                iter2->second[0][2] == 2);
    iter2 = bitInfo.find(1183);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0].size() == 2 &&
                iter2->second[0][0] == 1);
    TEST_ASSERT(iter2 != bitInfo.end() && iter2->second[0].size() == 2 &&
                iter2->second[0][1] == 2);
    delete fp1;
    delete m1;
  }
}

void testGitHubIssue874() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog)
      << "    Single atoms setting radius 1 bits in Morgan fingerprints  "
      << std::endl;
  {
    std::string smiles = "Cl";
    ROMol *m1 = SmilesToMol(smiles);
    TEST_ASSERT(m1);
    TEST_ASSERT(m1->getNumAtoms() == 1);

    SparseIntVect<std::uint32_t> *fp;
    fp = MorganFingerprints::getFingerprint(*m1, 0);
    TEST_ASSERT(fp->getNonzeroElements().size() == 1);
    delete fp;
    fp = MorganFingerprints::getFingerprint(*m1, 1);
    TEST_ASSERT(fp->getNonzeroElements().size() == 1);
    delete fp;

    delete m1;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue879() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "Github #879: Pattern fingerprint should set bits "
                           "for single-atom fragments."
                        << std::endl;
  {
    std::string smiles = "Cl";
    ROMol *m1 = SmilesToMol(smiles);
    TEST_ASSERT(m1);
    TEST_ASSERT(m1->getNumAtoms() == 1);

    ExplicitBitVect *bv = PatternFingerprintMol(*m1, 2048);
    TEST_ASSERT(bv);
    TEST_ASSERT(bv->getNumOnBits() == 2);
    delete bv;
    delete m1;
  }
  {
    std::string smiles = "Cl.[Na]";
    ROMol *m1 = SmilesToMol(smiles);
    TEST_ASSERT(m1);
    TEST_ASSERT(m1->getNumAtoms() == 2);

    ExplicitBitVect *bv = PatternFingerprintMol(*m1, 2048);
    TEST_ASSERT(bv);
    TEST_ASSERT(bv->getNumOnBits() == 4);
    delete bv;
    delete m1;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue1496() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "Github #1496: Pattern fingerprint setting bad bits "
                           "for degree zero atoms"
                        << std::endl;
  {
    std::string smiles = "C";
    ROMol *m1 = SmilesToMol(smiles);
    TEST_ASSERT(m1);
    TEST_ASSERT(m1->getNumAtoms() == 1);
    ExplicitBitVect *bv1 = PatternFingerprintMol(*m1, 2048);
    TEST_ASSERT(bv1);

    std::string smarts = "[#6]";
    ROMol *m2 = SmartsToMol(smarts);
    TEST_ASSERT(m2);
    TEST_ASSERT(m2->getNumAtoms() == 1);
    ExplicitBitVect *bv2 = PatternFingerprintMol(*m2, 2048);
    TEST_ASSERT(bv2);
    TEST_ASSERT(bv1->getNumOnBits() >= bv2->getNumOnBits())
    TEST_ASSERT(AllProbeBitsMatch(*bv2, *bv1));

    delete m1;
    delete bv1;
    delete m2;
    delete bv2;
  }
  {
    std::string smiles = "CC";
    ROMol *m1 = SmilesToMol(smiles);
    TEST_ASSERT(m1);
    TEST_ASSERT(m1->getNumAtoms() == 2);
    ExplicitBitVect *bv1 = PatternFingerprintMol(*m1, 2048);
    TEST_ASSERT(bv1);

    std::string smarts = "[#6]";
    ROMol *m2 = SmartsToMol(smarts);
    TEST_ASSERT(m2);
    TEST_ASSERT(m2->getNumAtoms() == 1);
    ExplicitBitVect *bv2 = PatternFingerprintMol(*m2, 2048);
    TEST_ASSERT(bv2);
    TEST_ASSERT(bv1->getNumOnBits() > bv2->getNumOnBits())
    TEST_ASSERT(AllProbeBitsMatch(*bv2, *bv1));

    delete m1;
    delete bv1;
    delete m2;
    delete bv2;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue1793() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "Github #1793: Fingerprint segfaults with "
                           "branchedPaths=False and useHs=False"
                        << std::endl;
  {
    std::string smiles = "CC";
    ROMol *m1 = SmilesToMol(smiles);
    TEST_ASSERT(m1);
    TEST_ASSERT(m1->getNumAtoms() == 2);

    unsigned int minPath = 1;
    unsigned int maxPath = 7;
    unsigned int fpSize = 2048;
    unsigned int nBitsPerHash = 2;
    double tgtDensity = 0.0;
    unsigned int minSize = 128;
    bool useHs = false;
    bool branchedPaths = false;

    ExplicitBitVect *bv1 =
        RDKFingerprintMol(*m1, minPath, maxPath, fpSize, nBitsPerHash, useHs,
                          tgtDensity, minSize, branchedPaths);
    TEST_ASSERT(bv1);
    delete m1;
    delete bv1;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue1993() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog)
      << "Github #1993: fingerprinters that use R/S labels should force a call "
         "to assignStereochemistry() if it hasn't already been called"
      << std::endl;
  {
    std::string smiles = "CC(F)(Cl)CC";
    std::unique_ptr<ROMol> m1(SmilesToMol(smiles));
    TEST_ASSERT(m1);
    TEST_ASSERT(m1->getNumAtoms() == 6);
    m1->clearProp(common_properties::_StereochemDone);
    std::unique_ptr<ROMol> m2(new ROMol(*m1));
    m2->getAtomWithIdx(1)->setChiralTag(Atom::CHI_TETRAHEDRAL_CW);
    std::unique_ptr<ROMol> m3(new ROMol(*m1));
    m3->getAtomWithIdx(1)->setChiralTag(Atom::CHI_TETRAHEDRAL_CCW);

    {  // mfp, no chirality
      bool useChirality = false;
      std::unique_ptr<SparseIntVect<std::uint32_t>> fp1(
          MorganFingerprints::getFingerprint(*m1, 1, nullptr, nullptr,
                                             useChirality));
      TEST_ASSERT(fp1);
      std::unique_ptr<SparseIntVect<std::uint32_t>> fp2(
          MorganFingerprints::getFingerprint(*m2, 1, nullptr, nullptr,
                                             useChirality));
      TEST_ASSERT(fp2);
      std::unique_ptr<SparseIntVect<std::uint32_t>> fp3(
          MorganFingerprints::getFingerprint(*m3, 1, nullptr, nullptr,
                                             useChirality));
      TEST_ASSERT(fp3);

      TEST_ASSERT((*fp1) == (*fp2));
      TEST_ASSERT((*fp1) == (*fp3));
      TEST_ASSERT((*fp2) == (*fp3));
    }

    {  // mfp, with chirality
      bool useChirality = true;
      std::unique_ptr<SparseIntVect<std::uint32_t>> fp1(
          MorganFingerprints::getFingerprint(*m1, 1, nullptr, nullptr,
                                             useChirality));
      TEST_ASSERT(fp1);
      std::unique_ptr<SparseIntVect<std::uint32_t>> fp2(
          MorganFingerprints::getFingerprint(*m2, 1, nullptr, nullptr,
                                             useChirality));
      TEST_ASSERT(fp2);
      std::unique_ptr<SparseIntVect<std::uint32_t>> fp3(
          MorganFingerprints::getFingerprint(*m3, 1, nullptr, nullptr,
                                             useChirality));
      TEST_ASSERT(fp3);

      TEST_ASSERT((*fp1) != (*fp2));
      TEST_ASSERT((*fp1) != (*fp3));
      TEST_ASSERT((*fp2) != (*fp3));
    }

    {  // ap, no chirality
      bool useChirality = false;
      std::unique_ptr<SparseIntVect<std::int32_t>> fp1(
          AtomPairs::getAtomPairFingerprint(*m1, nullptr, nullptr, nullptr,
                                            useChirality));
      TEST_ASSERT(fp1);
      std::unique_ptr<SparseIntVect<std::int32_t>> fp2(
          AtomPairs::getAtomPairFingerprint(*m2, nullptr, nullptr, nullptr,
                                            useChirality));
      TEST_ASSERT(fp2);
      std::unique_ptr<SparseIntVect<std::int32_t>> fp3(
          AtomPairs::getAtomPairFingerprint(*m3, nullptr, nullptr, nullptr,
                                            useChirality));
      TEST_ASSERT(fp3);

      TEST_ASSERT((*fp1) == (*fp2));
      TEST_ASSERT((*fp1) == (*fp3));
      TEST_ASSERT((*fp2) == (*fp3));
    }
    {  // ap, with chirality
      bool useChirality = true;
      std::unique_ptr<SparseIntVect<std::int32_t>> fp1(
          AtomPairs::getAtomPairFingerprint(*m1, nullptr, nullptr, nullptr,
                                            useChirality));
      TEST_ASSERT(fp1);
      std::unique_ptr<SparseIntVect<std::int32_t>> fp2(
          AtomPairs::getAtomPairFingerprint(*m2, nullptr, nullptr, nullptr,
                                            useChirality));
      TEST_ASSERT(fp2);
      std::unique_ptr<SparseIntVect<std::int32_t>> fp3(
          AtomPairs::getAtomPairFingerprint(*m3, nullptr, nullptr, nullptr,
                                            useChirality));
      TEST_ASSERT(fp3);

      TEST_ASSERT((*fp1) != (*fp2));
      TEST_ASSERT((*fp1) != (*fp3));
      TEST_ASSERT((*fp2) != (*fp3));
    }
    {  // ap, no chirality
      bool useChirality = false;
      unsigned int minLength = 1, maxLength = 10;
      std::unique_ptr<SparseIntVect<std::int32_t>> fp1(
          AtomPairs::getHashedAtomPairFingerprint(*m1, 2048, minLength,
                                                  maxLength, nullptr, nullptr,
                                                  nullptr, useChirality));
      TEST_ASSERT(fp1);
      std::unique_ptr<SparseIntVect<std::int32_t>> fp2(
          AtomPairs::getHashedAtomPairFingerprint(*m2, 2048, minLength,
                                                  maxLength, nullptr, nullptr,
                                                  nullptr, useChirality));
      TEST_ASSERT(fp2);
      std::unique_ptr<SparseIntVect<std::int32_t>> fp3(
          AtomPairs::getHashedAtomPairFingerprint(*m3, 2048, minLength,
                                                  maxLength, nullptr, nullptr,
                                                  nullptr, useChirality));
      TEST_ASSERT(fp3);

      TEST_ASSERT((*fp1) == (*fp2));
      TEST_ASSERT((*fp1) == (*fp3));
      TEST_ASSERT((*fp2) == (*fp3));
    }
    {  // ap, with chirality
      bool useChirality = true;
      unsigned int minLength = 1, maxLength = 10;
      std::unique_ptr<SparseIntVect<std::int32_t>> fp1(
          AtomPairs::getHashedAtomPairFingerprint(*m1, 2048, minLength,
                                                  maxLength, nullptr, nullptr,
                                                  nullptr, useChirality));
      TEST_ASSERT(fp1);
      std::unique_ptr<SparseIntVect<std::int32_t>> fp2(
          AtomPairs::getHashedAtomPairFingerprint(*m2, 2048, minLength,
                                                  maxLength, nullptr, nullptr,
                                                  nullptr, useChirality));
      TEST_ASSERT(fp2);
      std::unique_ptr<SparseIntVect<std::int32_t>> fp3(
          AtomPairs::getHashedAtomPairFingerprint(*m3, 2048, minLength,
                                                  maxLength, nullptr, nullptr,
                                                  nullptr, useChirality));
      TEST_ASSERT(fp3);

      TEST_ASSERT((*fp1) != (*fp2));
      TEST_ASSERT((*fp1) != (*fp3));
      TEST_ASSERT((*fp2) != (*fp3));
    }

    {  // tt, no chirality
      bool useChirality = false;
      std::unique_ptr<SparseIntVect<boost::int64_t>> fp1(
          AtomPairs::getTopologicalTorsionFingerprint(*m1, 4, nullptr, nullptr,
                                                      nullptr, useChirality));
      TEST_ASSERT(fp1);
      std::unique_ptr<SparseIntVect<boost::int64_t>> fp2(
          AtomPairs::getTopologicalTorsionFingerprint(*m2, 4, nullptr, nullptr,
                                                      nullptr, useChirality));
      TEST_ASSERT(fp2);
      std::unique_ptr<SparseIntVect<boost::int64_t>> fp3(
          AtomPairs::getTopologicalTorsionFingerprint(*m3, 4, nullptr, nullptr,
                                                      nullptr, useChirality));
      TEST_ASSERT(fp3);

      TEST_ASSERT((*fp1) == (*fp2));
      TEST_ASSERT((*fp1) == (*fp3));
      TEST_ASSERT((*fp2) == (*fp3));
    }
    {  // tt, with chirality
      bool useChirality = true;
      std::unique_ptr<SparseIntVect<boost::int64_t>> fp1(
          AtomPairs::getTopologicalTorsionFingerprint(*m1, 4, nullptr, nullptr,
                                                      nullptr, useChirality));
      TEST_ASSERT(fp1);
      std::unique_ptr<SparseIntVect<boost::int64_t>> fp2(
          AtomPairs::getTopologicalTorsionFingerprint(*m2, 4, nullptr, nullptr,
                                                      nullptr, useChirality));
      TEST_ASSERT(fp2);
      std::unique_ptr<SparseIntVect<boost::int64_t>> fp3(
          AtomPairs::getTopologicalTorsionFingerprint(*m3, 4, nullptr, nullptr,
                                                      nullptr, useChirality));
      TEST_ASSERT(fp3);

      TEST_ASSERT((*fp1) != (*fp2));
      TEST_ASSERT((*fp1) != (*fp3));
      TEST_ASSERT((*fp2) != (*fp3));
    }
    {  // tt, no chirality
      bool useChirality = false;
      std::unique_ptr<SparseIntVect<boost::int64_t>> fp1(
          AtomPairs::getHashedTopologicalTorsionFingerprint(
              *m1, 2048, 4, nullptr, nullptr, nullptr, useChirality));
      TEST_ASSERT(fp1);
      std::unique_ptr<SparseIntVect<boost::int64_t>> fp2(
          AtomPairs::getHashedTopologicalTorsionFingerprint(
              *m2, 2048, 4, nullptr, nullptr, nullptr, useChirality));
      TEST_ASSERT(fp2);
      std::unique_ptr<SparseIntVect<boost::int64_t>> fp3(
          AtomPairs::getHashedTopologicalTorsionFingerprint(
              *m3, 2048, 4, nullptr, nullptr, nullptr, useChirality));
      TEST_ASSERT(fp3);

      TEST_ASSERT((*fp1) == (*fp2));
      TEST_ASSERT((*fp1) == (*fp3));
      TEST_ASSERT((*fp2) == (*fp3));
    }
    {  // tt, with chirality
      bool useChirality = true;
      std::unique_ptr<SparseIntVect<boost::int64_t>> fp1(
          AtomPairs::getHashedTopologicalTorsionFingerprint(
              *m1, 2048, 4, nullptr, nullptr, nullptr, useChirality));
      TEST_ASSERT(fp1);
      std::unique_ptr<SparseIntVect<boost::int64_t>> fp2(
          AtomPairs::getHashedTopologicalTorsionFingerprint(
              *m2, 2048, 4, nullptr, nullptr, nullptr, useChirality));
      TEST_ASSERT(fp2);
      std::unique_ptr<SparseIntVect<boost::int64_t>> fp3(
          AtomPairs::getHashedTopologicalTorsionFingerprint(
              *m3, 2048, 4, nullptr, nullptr, nullptr, useChirality));
      TEST_ASSERT(fp3);

      TEST_ASSERT((*fp1) != (*fp2));
      TEST_ASSERT((*fp1) != (*fp3));
      TEST_ASSERT((*fp2) != (*fp3));
    }
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue2115() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog)
      << "Github #2115: BitInfo not complete for RDKFingerprint" << std::endl;
  {
    auto mol = "c1ccccc1O"_smiles;
    TEST_ASSERT(mol);

    unsigned int minPath = 1;
    unsigned int maxPath = 7;
    unsigned int fpSize = 2048;
    unsigned int nBitsPerHash = 2;
    bool useHs = true;
    double tgtDensity = 0.0;
    unsigned int minSize = 128;
    bool branchedPaths = true;
    bool useBondOrder = true;
    std::vector<std::uint32_t> *atomInvariants = nullptr;
    const std::vector<std::uint32_t> *fromAtoms = nullptr;
    std::vector<std::vector<std::uint32_t>> *atomBits = nullptr;
    std::map<std::uint32_t, std::vector<std::vector<int>>> bitInfo;

    std::unique_ptr<ExplicitBitVect> fp1(
        RDKFingerprintMol(*mol, minPath, maxPath, fpSize, nBitsPerHash, useHs,
                          tgtDensity, minSize, branchedPaths, useBondOrder,
                          atomInvariants, fromAtoms, atomBits, &bitInfo));
    TEST_ASSERT(fp1->getNumOnBits() == bitInfo.size());
  }

  {  // test that for atomBits too
    auto m1("CCCO"_smiles);
    TEST_ASSERT(m1);
    std::vector<std::vector<std::uint32_t>> atomBits(m1->getNumAtoms());
    unsigned int minPath = 1;
    unsigned int maxPath = 2;
    unsigned int fpSize = 2048;
    unsigned int nBitsPerHash = 2;
    bool useHs = true;
    double tgtDensity = 0.0;
    unsigned int minSize = 128;
    bool branchedPaths = true;
    bool useBondOrder = true;
    std::vector<std::uint32_t> *atomInvariants = nullptr;
    const std::vector<std::uint32_t> *fromAtoms = nullptr;

    std::unique_ptr<ExplicitBitVect> fp1(RDKFingerprintMol(
        *m1, minPath, maxPath, fpSize, nBitsPerHash, useHs, tgtDensity, minSize,
        branchedPaths, useBondOrder, atomInvariants, fromAtoms, &atomBits));
    TEST_ASSERT(fp1->getNumOnBits() == 8);
    TEST_ASSERT(atomBits[0].size() == 4);
    TEST_ASSERT(atomBits[1].size() == 6);
    TEST_ASSERT(atomBits[2].size() == 8);
    TEST_ASSERT(atomBits[3].size() == 4);
  }

  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue3723() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog)
      << "Github #3723: Fingerprint crash for mols with Zero order bonds"
      << std::endl;

  auto molblock = R"CTAB(mol
     RDKit          3D

  7  6  0  0  0  0  0  0  0  0999 V2000
   -0.0922   -0.0921   -0.0922 Al  0  0  0  0  0  3  0  0  0  0  0  0
    0.0770   -0.1091   -2.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576   -0.1093   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0560    0.0769   -0.1091 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207    1.8576   -0.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1091   -2.0561    0.0770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1093   -0.1207    1.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  1  1  0
  6  1  1  0
  7  1  1  0
M  ZBO  3   1   0   3   0   5   0
M  HYD  4   1   0   2   3   4   3   6   3
M  END)CTAB";
  std::unique_ptr<ROMol> mol{MolBlockToMol(molblock)};

  TEST_ASSERT(AtomPairs::getAtomCode(mol->getAtomWithIdx(0), 0, false) == 486);
}

int main(int argc, char *argv[]) {
  (void)argc;
  (void)argv;
  RDLog::InitLogs();
  test1();
  test2();
  test3();
  test1alg2();
  test2alg2();
  test4Trends();
  test1Layers();
  test2Layers();
  test3Layers();
  test1MorganFPs();
  test2MorganFPsFromAtoms();
  test3MorganFPs();
  test4MorganFPs();
  test5MorganFPs();
  // test5BackwardsCompatibility();
  // testIssue2875658();
  testAtomCodes();
  testAtomPairs();
  testAtomPairs2();
  testTorsions();
  testBulkTorsions();
  testHashedAtomPairs();
  testHashedTorsions();
  testRootedAtomPairs();
  testIgnoreAtomPairs();
  testRootedTorsions();
  testIgnoreTorsions();
  testMorganAtomInfo();
  testMorganAtomInfoRedundantEnv();
  testRDKitFPOptions();
  testPairsAndTorsionsOptions();
  testMACCS();
  testRDKitFromAtoms();
  testRDKitAtomBits();
  testChiralPairs();
  testChiralTorsions();
  testGitHubIssue25();
  testGitHubIssue151();
  test3DAtomPairs();
  testGitHubIssue195();
  testMultithreadedPatternFP();
  testGitHubIssue258();
  testGitHubIssue334();
  testGitHubIssue695();
  testGitHubIssue811();
  testRDKFPUnfolded();
  testRDKFPBitInfo();
  testGitHubIssue874();
  testGitHubIssue879();
  testGitHubIssue1496();
  testGitHubIssue1793();
  testGitHubIssue1993();
  testGitHubIssue2115();
  testGitHubIssue3723();

  return 0;
}