//
//  Copyright (C) 2001-2017 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.
//
//

// std bits
#include <RDGeneral/test.h>
#include <iostream>

// RD bits
#include <GraphMol/RDKitBase.h>
#include <GraphMol/RDKitQueries.h>
#include <GraphMol/Chirality.h>
#include "SubstructMatch.h"
#include "SubstructUtils.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>

using namespace RDKit;

void test1() {
  std::cout << " ----------------- Test 1" << std::endl;
  MatchVectType matchV;
  std::vector<MatchVectType> matches;
  unsigned int n;

  RWMol *m, *q1;
  bool updateLabel = true;
  bool takeOwnership = true;
  m = new RWMol();
  m->addAtom(new Atom(8), updateLabel, takeOwnership);
  m->addAtom(new Atom(6), updateLabel, takeOwnership);
  m->addAtom(new Atom(6), updateLabel, takeOwnership);
  m->addBond(0, 1, Bond::SINGLE);
  m->addBond(1, 2, Bond::SINGLE);

  q1 = new RWMol();
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addBond(0, 1, Bond::SINGLE);
  n = SubstructMatch(*m, *q1, matches, false);
  CHECK_INVARIANT(n == 2, "");
  CHECK_INVARIANT(matches.size() == n, "");
  CHECK_INVARIANT(matches[0].size() == 2, "");
  TEST_ASSERT(matches[0][0].first == 0);
  TEST_ASSERT(matches[0][0].second == 1 || matches[0][0].second == 2);
  TEST_ASSERT(matches[0][1].first == 1);
  TEST_ASSERT(matches[0][1].second != matches[0][0].second);

  TEST_ASSERT(matches[1][1].second == 1 || matches[0][1].second == 2);
  TEST_ASSERT(matches[1][0].first == 0);
  TEST_ASSERT(matches[1][0].second == 1 || matches[1][0].second == 2);
  TEST_ASSERT(matches[1][0].second != matches[0][0].second);
  TEST_ASSERT(matches[1][0].second == matches[0][1].second);
  TEST_ASSERT(matches[1][1].first == 1);
  TEST_ASSERT(matches[1][1].second != matches[1][0].second);
  TEST_ASSERT(matches[1][1].second == matches[0][0].second);

  n = SubstructMatch(*m, *q1, matches, true);
  CHECK_INVARIANT(n == 1, "");
  CHECK_INVARIANT(matches.size() == n, "");
  CHECK_INVARIANT(matches[0].size() == 2, "");
  TEST_ASSERT(matches[0][0].first == 0);
  TEST_ASSERT(matches[0][0].second == 1 || matches[0][0].second == 2);
  TEST_ASSERT(matches[0][1].first == 1);
  TEST_ASSERT(matches[0][1].second != matches[0][0].second);
  TEST_ASSERT(matches[0][1].second == 1 || matches[0][1].second == 2);

  CHECK_INVARIANT(SubstructMatch(*m, *q1, matchV), "");
  CHECK_INVARIANT(matchV.size() == 2, "");

  // make sure we reset the match vectors.
  // build a query we won't match:
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addBond(1, 2, Bond::SINGLE);
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addBond(2, 3, Bond::SINGLE);

  TEST_ASSERT(!SubstructMatch(*m, *q1, matchV));
  TEST_ASSERT(matchV.size() == 0);

  n = SubstructMatch(*m, *q1, matches, false);
  TEST_ASSERT(n == 0);
  TEST_ASSERT(matches.size() == 0);

  delete m;
  delete q1;
  std::cout << "Done\n" << std::endl;
}

void test2() {
  std::cout << " ----------------- Test 2" << std::endl;
  MatchVectType matchV;
  std::vector<MatchVectType> matches;
  unsigned int n;

  RWMol *m, *q1;
  m = new RWMol();
  bool updateLabel = true;
  bool takeOwnership = true;
  m->addAtom(new Atom(6), updateLabel, takeOwnership);
  m->addAtom(new Atom(6), updateLabel, takeOwnership);
  m->addAtom(new Atom(8), updateLabel, takeOwnership);
  m->addBond(0, 1, Bond::SINGLE);
  m->addBond(1, 2, Bond::SINGLE);

  q1 = new RWMol();
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(8), updateLabel, takeOwnership);
  q1->addBond(0, 1, Bond::SINGLE);

  n = SubstructMatch(*m, *q1, matchV);
  TEST_ASSERT(n);
  TEST_ASSERT(matchV.size() == 2);
  TEST_ASSERT(matchV[0].first == 0);
  TEST_ASSERT(matchV[0].second == 1);
  TEST_ASSERT(matchV[1].first == 1);
  TEST_ASSERT(matchV[1].second == 2);

  n = SubstructMatch(*m, *q1, matches, false);
  CHECK_INVARIANT(n == 1, "");
  CHECK_INVARIANT(matches.size() == n, "");
  CHECK_INVARIANT(matches[0].size() == 2, "");
  n = SubstructMatch(*m, *q1, matches, true);
  CHECK_INVARIANT(n == 1, "");
  CHECK_INVARIANT(matches.size() == n, "");
  CHECK_INVARIANT(matches[0].size() == 2, "");

  CHECK_INVARIANT(SubstructMatch(*m, *q1, matchV), "");
  CHECK_INVARIANT(matchV.size() == 2, "");

  delete m;
  m = new RWMol();
  m->addAtom(new Atom(6), updateLabel, takeOwnership);
  m->addAtom(new Atom(6), updateLabel, takeOwnership);
  m->addAtom(new Atom(8), updateLabel, takeOwnership);
  m->addBond(0, 1, Bond::SINGLE);
  m->addBond(1, 2, Bond::DOUBLE);

  matches.clear();
  n = SubstructMatch(*m, *q1, matches, false);
  CHECK_INVARIANT(n == 0, "");
  CHECK_INVARIANT(matches.size() == n, "");
  n = SubstructMatch(*m, *q1, matches, true);
  CHECK_INVARIANT(n == 0, "");
  CHECK_INVARIANT(matches.size() == n, "");
  CHECK_INVARIANT(!SubstructMatch(*m, *q1, matchV), "");
  delete m;
  delete q1;

  std::cout << "Done\n" << std::endl;
}

void test3() {
  std::cout << " ----------------- Test 3" << std::endl;
  MatchVectType matchV;
  std::vector<MatchVectType> matches;
  unsigned int n;

  RWMol *m, *q1;
  m = new RWMol();
  bool updateLabel = true;
  bool takeOwnership = true;
  m->addAtom(new Atom(6), updateLabel, takeOwnership);
  m->addAtom(new Atom(6), updateLabel, takeOwnership);
  m->addAtom(new Atom(8), updateLabel, takeOwnership);
  m->addBond(0, 1, Bond::SINGLE);
  m->addBond(1, 2, Bond::SINGLE);

  q1 = new RWMol();
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(8), updateLabel, takeOwnership);
  q1->addBond(0, 1, Bond::UNSPECIFIED);
  n = SubstructMatch(*m, *q1, matches, false);
  CHECK_INVARIANT(n == 1, "");
  CHECK_INVARIANT(matches.size() == n, "");
  CHECK_INVARIANT(matches[0].size() == 2, "");
  n = SubstructMatch(*m, *q1, matches, true);
  CHECK_INVARIANT(n == 1, "");
  CHECK_INVARIANT(matches.size() == n, "");
  CHECK_INVARIANT(matches[0].size() == 2, "");

  CHECK_INVARIANT(SubstructMatch(*m, *q1, matchV), "");
  CHECK_INVARIANT(matchV.size() == 2, "");

  delete m;
  m = new RWMol();
  m->addAtom(new Atom(6), updateLabel, takeOwnership);
  m->addAtom(new Atom(6), updateLabel, takeOwnership);
  m->addAtom(new Atom(8), updateLabel, takeOwnership);
  m->addBond(0, 1, Bond::SINGLE);
  m->addBond(1, 2, Bond::DOUBLE);

  matches.clear();
  n = SubstructMatch(*m, *q1, matches, false);
  CHECK_INVARIANT(n == 1, "");
  CHECK_INVARIANT(matches.size() == n, "");
  CHECK_INVARIANT(matches[0].size() == 2, "");
  n = SubstructMatch(*m, *q1, matches, true);
  CHECK_INVARIANT(n == 1, "");
  CHECK_INVARIANT(matches.size() == n, "");
  CHECK_INVARIANT(matches[0].size() == 2, "");

  CHECK_INVARIANT(SubstructMatch(*m, *q1, matchV), "");
  CHECK_INVARIANT(matchV.size() == 2, "");

  delete q1;
  q1 = new RWMol();
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addBond(0, 1, Bond::UNSPECIFIED);
  n = SubstructMatch(*m, *q1, matches, false);
  TEST_ASSERT(n == 2);
  TEST_ASSERT(matches.size() == n);
  TEST_ASSERT(matches[0].size() == 2);
  TEST_ASSERT(matches[1].size() == 2);
  TEST_ASSERT(matches[0][0].second != matches[1][0].second);
  TEST_ASSERT(matches[0][1].second != matches[1][1].second);
  n = SubstructMatch(*m, *q1, matches, true);
  TEST_ASSERT(n == 1);
  TEST_ASSERT(matches.size() == n);

  delete m;
  delete q1;
  std::cout << "Done\n" << std::endl;
}

void test4() {
  std::cout << " ----------------- Test 4" << std::endl;
  MatchVectType matchV;
  std::vector<MatchVectType> matches;
  int n;
  bool updateLabel = true;
  bool takeOwnership = true;

  RWMol *m, *q1, *q2;
  auto *a6 = new Atom(6);
  auto *a8 = new Atom(8);
  m = new RWMol();
  m->addAtom(a6);
  m->addAtom(a6);
  m->addAtom(a8);
  m->addAtom(a6);
  m->addAtom(a6);
  m->addBond(1, 0, Bond::SINGLE);
  m->addBond(1, 2, Bond::SINGLE);
  m->addBond(1, 3, Bond::SINGLE);
  m->addBond(2, 4, Bond::SINGLE);

  // this will be the recursive query
  q1 = new RWMol();
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(8), updateLabel, takeOwnership);
  q1->addBond(0, 1, Bond::UNSPECIFIED);

  // here's the main query
  q2 = new RWMol();
  auto *qA = new QueryAtom(6);
  auto *rsq = new RecursiveStructureQuery(q1);
  qA->expandQuery(rsq, Queries::COMPOSITE_AND);
  // std::cout << "post expand: " << qA->getQuery() << std::endl;
  q2->addAtom(qA, true, true);
  // std::cout << "mol: " << q2->getAtomWithIdx(0)->getQuery() << std::endl;
  q2->addAtom(new QueryAtom(6), true, true);
  q2->addBond(0, 1, Bond::UNSPECIFIED);

  bool found = SubstructMatch(*m, *q2, matchV);
  CHECK_INVARIANT(found, "");
  CHECK_INVARIANT(matchV.size() == 2, "");
  TEST_ASSERT(matchV[0].first == 0);
  TEST_ASSERT(matchV[0].second == 1);
  TEST_ASSERT(matchV[1].first == 1);
  TEST_ASSERT(matchV[1].second == 0 || matchV[1].second == 3);
  n = SubstructMatch(*m, *q2, matches, true);
  TEST_ASSERT(n == 2);
  TEST_ASSERT(matches.size() == (size_t)n);
  TEST_ASSERT(matches[0].size() == 2);
  TEST_ASSERT(matches[1].size() == 2);
  TEST_ASSERT(matches[0][0].second == matches[1][0].second);
  TEST_ASSERT(matches[0][1].second != matches[1][1].second);
  delete m;
  delete a6;
  delete a8;
  delete q2;

  std::cout << "Done\n" << std::endl;
}

void test5() {
  std::cout << " ----------------- Test 5" << std::endl;
  MatchVectType matchV;
  std::vector<MatchVectType> matches;
  int n;
  bool updateLabel = true;
  bool takeOwnership = true;

  RWMol *m, *q1, *q2;
  auto *a6 = new Atom(6);
  auto *a8 = new Atom(8);
  // CC(OC)C
  m = new RWMol();
  m->addAtom(a6);
  m->addAtom(a6);
  m->addAtom(a8);
  m->addAtom(a6);
  m->addAtom(a6);
  m->addBond(0, 1, Bond::SINGLE);
  m->addBond(1, 2, Bond::SINGLE);
  m->addBond(1, 4, Bond::SINGLE);
  m->addBond(2, 3, Bond::SINGLE);

  // this will be the recursive query
  q1 = new RWMol();
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(8), updateLabel, takeOwnership);
  q1->addBond(0, 1, Bond::UNSPECIFIED);

  // here's the main query
  q2 = new RWMol();
  auto *qA = new QueryAtom();
  auto *rsq = new RecursiveStructureQuery(q1);
  qA->setQuery(rsq);
  q2->addAtom(qA, true, true);
  q2->addAtom(new QueryAtom(6), true, true);
  q2->addBond(0, 1, Bond::UNSPECIFIED);

  bool found = SubstructMatch(*m, *q2, matchV);
  CHECK_INVARIANT(found, "");
  CHECK_INVARIANT(matchV.size() == 2, "");
  n = SubstructMatch(*m, *q2, matches, true);
  CHECK_INVARIANT(n == 2, "");
  CHECK_INVARIANT(matches[0].size() == 2, "");
  delete m;
  delete a6;
  delete a8;
  delete q2;

  std::cout << "Done\n" << std::endl;
}
void test5QueryRoot() {
  std::cout << " ----------------- Test 5 QueryRoot" << std::endl;
  MatchVectType matchV;
  std::vector<MatchVectType> matches;
  int n;
  bool updateLabel = true;
  bool takeOwnership = true;

  RWMol *m, *q1, *q2;
  auto *a6 = new Atom(6);
  auto *a8 = new Atom(8);
  // CC(OC)C
  m = new RWMol();
  m->addAtom(a6);
  m->addAtom(a6);
  m->addAtom(a8);
  m->addAtom(a6);
  m->addAtom(a6);
  m->addBond(0, 1, Bond::SINGLE);
  m->addBond(1, 2, Bond::SINGLE);
  m->addBond(1, 4, Bond::SINGLE);
  m->addBond(2, 3, Bond::SINGLE);

  // this will be the recursive query
  q1 = new RWMol();
  q1->addAtom(new QueryAtom(8), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addBond(0, 1, Bond::UNSPECIFIED);
  q1->setProp(common_properties::_queryRootAtom, 1);

  // here's the main query
  q2 = new RWMol();
  auto *qA = new QueryAtom();
  auto *rsq = new RecursiveStructureQuery(q1);
  qA->setQuery(rsq);
  q2->addAtom(qA, true, true);
  q2->addAtom(new QueryAtom(6), true, true);
  q2->addBond(0, 1, Bond::UNSPECIFIED);

  bool found = SubstructMatch(*m, *q2, matchV);
  CHECK_INVARIANT(found, "");
  CHECK_INVARIANT(matchV.size() == 2, "");
  n = SubstructMatch(*m, *q2, matches, true);
  CHECK_INVARIANT(n == 2, "");
  CHECK_INVARIANT(matches[0].size() == 2, "");
  delete m;
  delete a6;
  delete a8;
  delete q2;

  std::cout << "Done\n" << std::endl;
}

void test6() {
  std::cout << " ----------------- Test 6 (Issue71 related)" << std::endl;
  MatchVectType matchV;
  std::vector<MatchVectType> matches;
  int n;
  bool updateLabel = true;
  bool takeOwnership = true;

  RWMol *m, *q1;
  auto *a6 = new Atom(6);

  m = new RWMol();
  m->addAtom(a6);
  m->addAtom(a6);
  m->addAtom(a6);
  m->addBond(0, 1, Bond::SINGLE);
  m->addBond(1, 2, Bond::SINGLE);
  m->addBond(0, 2, Bond::SINGLE);

  q1 = new RWMol();
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addBond(0, 1, Bond::UNSPECIFIED);
  q1->addBond(1, 2, Bond::UNSPECIFIED);

  bool found = SubstructMatch(*m, *q1, matchV);
  CHECK_INVARIANT(found, "");
  CHECK_INVARIANT(matchV.size() == 3, "");
  n = SubstructMatch(*m, *q1, matches, true);
  CHECK_INVARIANT(n == 1, "");
  CHECK_INVARIANT(matches[0].size() == 3, "");

  // close the loop and try again (we should still match)
  q1->addBond(0, 2, Bond::UNSPECIFIED);
  found = SubstructMatch(*m, *q1, matchV);
  CHECK_INVARIANT(found, "");
  CHECK_INVARIANT(matchV.size() == 3, "");
  n = SubstructMatch(*m, *q1, matches, true);
  CHECK_INVARIANT(n == 1, "");
  CHECK_INVARIANT(matches[0].size() == 3, "");
  delete m;
  delete a6;
  delete q1;

  std::cout << "Done\n" << std::endl;
}

void test7() {
  std::cout << " ----------------- Test 7 (leak check)" << std::endl;
  MatchVectType matchV;
  int n;

  RWMol *m, *q1;
  auto *a6 = new Atom(6);
  bool updateLabel = true;
  bool takeOwnership = true;

  m = new RWMol();
  m->addAtom(a6);
  m->addAtom(a6);
  m->addAtom(a6);
  m->addBond(0, 1, Bond::SINGLE);
  m->addBond(1, 2, Bond::SINGLE);
  m->addBond(0, 2, Bond::SINGLE);

  q1 = new RWMol();
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addBond(0, 1, Bond::UNSPECIFIED);
  q1->addBond(1, 2, Bond::UNSPECIFIED);

  bool found = SubstructMatch(*m, *q1, matchV);
  CHECK_INVARIANT(found, "");
  CHECK_INVARIANT(matchV.size() == 3, "");
  std::vector<MatchVectType> matches;
  for (int i = 0; i < 300000; i++) {
    n = SubstructMatch(*m, *q1, matches, true, true);
    CHECK_INVARIANT(n == 1, "");
    CHECK_INVARIANT(matches[0].size() == 3, "");
    if (!(i % 500)) {
      std::cout << i << std::endl;
    }
  }
  delete m;
  delete a6;
  delete q1;

  std::cout << "Done\n" << std::endl;
}

#ifdef CACHE_ARMOLGRAPHS
void test8() {
  std::cout << " ----------------- Test 8 (molgraph cache)" << std::endl;
  MatchVectType matchV;
  int n;

  RWMol *m, *q1;
  Atom *a6 = new Atom(6);

  m = new RWMol();
  m->addAtom(a6);
  m->addAtom(a6);
  m->addAtom(a6);
  m->addBond(0, 1, Bond::SINGLE);
  m->addBond(1, 2, Bond::SINGLE);
  m->addBond(0, 2, Bond::SINGLE);

  q1 = new RWMol();
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
  q1->addBond(0, 1, Bond::UNSPECIFIED);
  q1->addBond(1, 2, Bond::UNSPECIFIED);

  bool found = SubstructMatch(*m, *q1, matchV);
  CHECK_INVARIANT(found, "");
  CHECK_INVARIANT(matchV.size() == 3, "");
  std::vector<MatchVectType> matches;
  for (int i = 0; i < 30000; i++) {
    n = SubstructMatch(*m, *q1, matches, true, true);
    CHECK_INVARIANT(n == 1, "");
    CHECK_INVARIANT(matches[0].size() == 3, "");
    if (!(i % 500)) std::cout << i << std::endl;
  }
  delete m;
  delete a6;
  delete q1;

  std::cout << "Done\n" << std::endl;
}
#endif

void test9() {
  std::cout << " ----------------- Test 9 (chiral searches)" << std::endl;
  MatchVectType matchV;
  std::vector<MatchVectType> matches;
  int n;

  RWMol *m, *q1;
  auto *a6 = new Atom(6);

  m = new RWMol();
  bool updateLabel = true;
  bool takeOwnership = true;
  m->addAtom(a6);
  m->addAtom(new Atom(6), updateLabel, takeOwnership);
  m->addAtom(new Atom(7), updateLabel, takeOwnership);
  m->addAtom(new Atom(8), updateLabel, takeOwnership);
  m->addAtom(new Atom(9), updateLabel, takeOwnership);
  m->addBond(0, 1, Bond::SINGLE);
  m->addBond(0, 2, Bond::SINGLE);
  m->addBond(0, 3, Bond::SINGLE);
  m->addBond(0, 4, Bond::SINGLE);
  m->getAtomWithIdx(0)->setChiralTag(Atom::CHI_TETRAHEDRAL_CW);

  q1 = new RWMol();
  q1->addAtom(a6);
  q1->addAtom(new Atom(6));
  q1->addAtom(new Atom(7));
  q1->addAtom(new Atom(8));
  q1->addAtom(new Atom(9));
  q1->addBond(0, 1, Bond::SINGLE);
  q1->addBond(0, 2, Bond::SINGLE);
  q1->addBond(0, 3, Bond::SINGLE);
  q1->addBond(0, 4, Bond::SINGLE);
  q1->getAtomWithIdx(0)->setChiralTag(Atom::CHI_TETRAHEDRAL_CCW);

  MolOps::sanitizeMol(*m);
  MolOps::assignStereochemistry(*m);
  MolOps::sanitizeMol(*q1);
  MolOps::assignStereochemistry(*q1);

  bool found;
  // test with default options (no chirality):
  found = SubstructMatch(*m, *q1, matchV);
  TEST_ASSERT(found);
  n = SubstructMatch(*m, *q1, matches, true);
  TEST_ASSERT(n == 1);

  // test with chirality
  found = SubstructMatch(*m, *q1, matchV, true, true);
  TEST_ASSERT(!found);
  n = SubstructMatch(*m, *q1, matches, true, true, true);
  TEST_ASSERT(n == 0);

  // self matches:
  found = SubstructMatch(*m, *m, matchV, true, true);
  TEST_ASSERT(found);
  n = SubstructMatch(*m, *m, matches, true, true, true);
  TEST_ASSERT(n == 1);
  found = SubstructMatch(*q1, *q1, matchV, true, true);
  TEST_ASSERT(found);
  n = SubstructMatch(*q1, *q1, matches, true, true, true);
  TEST_ASSERT(n == 1);
  delete m;
  delete a6;
  delete q1;

  std::cout << "Done\n" << std::endl;
}

void testRecursiveSerialNumbers() {
  std::cout << " ----------------- Testing serial numbers on recursive queries"
            << std::endl;
  MatchVectType matchV;
  std::vector<MatchVectType> matches;
  int n;
  bool updateLabel = true;
  bool takeOwnership = true;

  RWMol *m, *q1, *q2;
  auto *a6 = new Atom(6);
  auto *a8 = new Atom(8);
  m = new RWMol();
  m->addAtom(a6);
  m->addAtom(a6);
  m->addAtom(a8);
  m->addAtom(a6);
  m->addAtom(a6);
  m->addBond(1, 0, Bond::SINGLE);
  m->addBond(1, 2, Bond::SINGLE);
  m->addBond(1, 3, Bond::SINGLE);
  m->addBond(2, 4, Bond::SINGLE);

  {
    // this will be the recursive query
    q1 = new RWMol();
    q1->addAtom(new QueryAtom(6), updateLabel, takeOwnership);
    q1->addAtom(new QueryAtom(8), updateLabel, takeOwnership);
    q1->addBond(0, 1, Bond::UNSPECIFIED);

    // here's the main query
    q2 = new RWMol();
    auto *qA = new QueryAtom(6);
    auto *rsq = new RecursiveStructureQuery(new RWMol(*q1), 1);
    qA->expandQuery(rsq, Queries::COMPOSITE_AND);
    // std::cout << "post expand: " << qA->getQuery() << std::endl;
    q2->addAtom(qA, true, true);
    // std::cout << "mol: " << q2->getAtomWithIdx(0)->getQuery() << std::endl;
    q2->addAtom(new QueryAtom(8), true, true);
    q2->addBond(0, 1, Bond::UNSPECIFIED);

    qA = new QueryAtom(6);
    rsq = new RecursiveStructureQuery(new RWMol(*q1), 1);
    qA->expandQuery(rsq, Queries::COMPOSITE_AND);
    q2->addAtom(qA, true, true);
    q2->addBond(1, 2, Bond::UNSPECIFIED);

    bool found = SubstructMatch(*m, *q2, matchV);
    CHECK_INVARIANT(found, "");
    CHECK_INVARIANT(matchV.size() == 3, "");
    n = SubstructMatch(*m, *q2, matches, true);
    TEST_ASSERT(n == 1);
    TEST_ASSERT(matches.size() == 1);
    TEST_ASSERT(matches[0].size() == 3);
    delete q1;
    delete q2;
  }
  delete m;
  delete a6;
  delete a8;
  std::cout << "Done\n" << std::endl;
}

#ifdef RDK_TEST_MULTITHREADED
#include <RDGeneral/BoostStartInclude.h>
#include <thread>
#include <future>
#include <boost/dynamic_bitset.hpp>
#include <RDGeneral/BoostEndInclude.h>
namespace {
void runblock(const std::vector<ROMol *> &mols, const ROMol *query,
              const boost::dynamic_bitset<> &hits, unsigned int count,
              unsigned int idx) {
  for (unsigned int j = 0; j < 100; j++) {
    for (unsigned int i = 0; i < mols.size(); ++i) {
      if (i % count != idx) {
        continue;
      }
      ROMol *mol = mols[i];

      MatchVectType matchV;
      bool found = SubstructMatch(*mol, *query, matchV);

      TEST_ASSERT(found == hits[i]);
    }
  }
};
}  // namespace
void testMultiThread() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test multithreading" << 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;
  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;
  ROMol *query = SmartsToMol("[#6;$([#6]([#6])[!#6])]");
  boost::dynamic_bitset<> hits(mols.size());
  for (unsigned int i = 0; i < mols.size(); ++i) {
    MatchVectType matchV;
    hits[i] = SubstructMatch(*mols[i], *query, matchV);
  }
  unsigned int count = 4;
#if 1
  std::cerr << " hits: " << hits << std::endl;
  std::cerr << "processing" << 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, query, hits, count, i));
  }
  for (auto &fut : tg) {
    fut.get();
  }
  tg.clear();
  std::cerr << " done" << std::endl;
  delete query;

  query = SmartsToMol("[#6]([#6])[!#6]");
  for (unsigned int i = 0; i < mols.size(); ++i) {
    MatchVectType matchV;
    hits[i] = SubstructMatch(*mols[i], *query, matchV);
  }
  std::cerr << " hits2: " << hits << std::endl;
  std::cerr << "processing2" << std::endl;
  for (unsigned int i = 0; i < count; ++i) {
    std::cerr << " launch2 :" << i << std::endl;
    std::cerr.flush();
    tg.emplace_back(
        std::async(std::launch::async, runblock, mols, query, hits, count, i));
  }
  for (auto &fut : tg) {
    fut.get();
  }
  tg.clear();
  std::cerr << " done" << std::endl;
  delete query;
#endif

  std::cerr << " preprocessing 3" << std::endl;
  query = SmartsToMol("[$([O,S]-[!$(*=O)])]");
  for (unsigned int i = 0; i < mols.size(); ++i) {
    MatchVectType matchV;
    hits[i] = SubstructMatch(*mols[i], *query, matchV);
  }
  std::cerr << " hits3: " << hits << std::endl;
  std::cerr << "processing3" << std::endl;
  for (unsigned int i = 0; i < count; ++i) {
    std::cerr << " launch3 :" << i << std::endl;
    std::cerr.flush();
    tg.emplace_back(
        std::async(std::launch::async, runblock, mols, query, hits, count, i));
  }
  for (auto &fut : tg) {
    fut.get();
  }
  std::cerr << " done" << std::endl;
  delete query;

  for (auto &mol : mols) {
    delete mol;
  }

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

void testChiralMatch() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test chiral matching" << std::endl;

  {
    std::string qSmi = "Cl[C@](C)(F)Br";
    std::string mSmi = "Cl[C@](C)(F)Br";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "Cl[C@](C)(F)Br";
    std::string mSmi = "Cl[C@@](C)(F)Br";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }
  {
    std::string qSmi = "Cl[C@](C)(F)Br";
    std::string mSmi = "Cl[C@@](F)(C)Br";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "Cl[C@](C)(F)Br";
    std::string mSmi = "Cl[C@](F)(C)Br";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }
  {
    std::string qSmi = "Cl[C@](C)(F)Br";
    std::string mSmi = "Cl[C@@](Br)(C)F";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }
  {
    std::string qSmi = "Cl[C@](C)(F)Br";
    std::string mSmi = "Cl[C@](Br)(C)F";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }

  {
    std::string qSmi = "C[C@](O)(F)Br";
    std::string mSmi = "O[C@](F)(Br)CC[C@](O)(F)Br";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }

  {
    std::string qSmi = "C[C@](O)(F)Br";
    std::string mSmi = "O[C@](F)(Br)CC[C@@](O)(F)Br";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }

  {
    std::string qSmi = "C[C@](O)(F)Br";
    std::string mSmi = "O[C@](F)(Br)CC(C[C@](O)(F)Br)C[C@](O)(F)Br";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    std::vector<MatchVectType> matches;
    int count = SubstructMatch(*mol, *query, matches, true, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(count == 2);
  }

  {
    std::string qSmi = "C[C@](O)(F)Br";
    std::string mSmi = "O[C@@](F)(Br)CC(C[C@](O)(F)Br)C[C@](O)(F)Br";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    std::vector<MatchVectType> matches;
    int count = SubstructMatch(*mol, *query, matches, true, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(count == 3);
  }
  {
    std::string qSmi = "C[C@](O)(F)Br";
    std::string mSmi = "O[C@](F)(Br)CC(C[C@@](O)(F)Br)C[C@](O)(F)Br";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    std::vector<MatchVectType> matches;
    int count = SubstructMatch(*mol, *query, matches, true, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(count == 1);
  }
  {
    std::string qSmi = "C[C@](O)(F)Br";
    std::string mSmi = "O[C@](F)(Br)CC(C[C@@](O)(F)Br)C[C@@](O)(F)Br";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    std::vector<MatchVectType> matches;
    // std::cerr<<"\n\n------------------------------------------\n"<<qSmi<<"
    // "<<mSmi<<"\n"<<std::endl;
    int count = SubstructMatch(*mol, *query, matches, true, true, true);
    // std::cerr<<"res: "<<count<<std::endl;
    delete mol;
    delete query;
    TEST_ASSERT(count == 0);
  }
  {
    std::string qSmi = "Cl[C@](*)(F)Br";
    std::string mSmi = "Cl[C@](C)(F)Br";
    ROMol *query = SmartsToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "Cl[C@@](*)(F)Br";
    std::string mSmi = "Cl[C@](C)(F)Br";
    ROMol *query = SmartsToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }
  {
    std::string qSmi = "Cl[C@](*)(*)Br";
    std::string mSmi = "Cl[C@](C)(F)Br";
    ROMol *query = SmartsToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "Cl[C@@](*)(*)Br";
    std::string mSmi = "Cl[C@](C)(F)Br";
    ROMol *query = SmartsToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "[C@](C)(F)Br";
    std::string mSmi = "Cl[C@](C)(F)Br";
    ROMol *query = SmartsToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }
  {
    std::string qSmi = "[C@@](C)(F)Br";
    std::string mSmi = "Cl[C@](C)(F)Br";
    ROMol *query = SmartsToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "C[C@](F)Br";
    std::string mSmi = "Cl[C@](C)(F)Br";
    ROMol *query = SmartsToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }
  {
    std::string qSmi = "C[C@@](F)Br";
    std::string mSmi = "Cl[C@](C)(F)Br";
    ROMol *query = SmartsToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "Cl[C@](F)Br";
    std::string mSmi = "Cl[C@](C)(F)Br";
    ROMol *query = SmartsToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "Cl[C@](C)F";
    std::string mSmi = "Cl[C@](C)(F)Br";
    ROMol *query = SmartsToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }

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

void testCisTransMatch() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test cis/trans matching" << std::endl;

  {
    std::string qSmi = "CC=CC";
    std::string mSmi = "CC=CC";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "CC=CC";
    std::string mSmi = "C/C=C/C";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "C/C=C/C";
    std::string mSmi = "CC=CC";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }
  {
    std::string qSmi = "C/C=C/C";
    std::string mSmi = "C/C=C\\C";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }
  {
    std::string qSmi = "C/C=C/C";
    std::string mSmi = "C/C=C/C";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "C/C=C/C";
    std::string mSmi = "C/C=C(/F)C";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }
  {
    std::string qSmi = "C/C=C/C";
    std::string mSmi = "C/C=C(\\F)C";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "C/C=C/C";
    std::string mSmi = "C/C(F)=C(\\F)C";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "C/C=C/C";
    std::string mSmi = "CC(/F)=C(\\F)C";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(matched);
  }
  {
    std::string qSmi = "C/C=C/C";
    std::string mSmi = "CC(\\F)=C(\\F)C";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }

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

void testCisTransMatch2() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test cis/trans matching part 2" << std::endl;

  {
    std::string qSmi = "CC=CC";
    std::string mSmi = "CCC=CC";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));

    TEST_ASSERT(query->getBondWithIdx(1)->getBondType() == Bond::DOUBLE);
    query->getBondWithIdx(1)->getStereoAtoms().push_back(0);
    query->getBondWithIdx(1)->getStereoAtoms().push_back(3);
    query->getBondWithIdx(1)->setStereo(Bond::STEREOCIS);
    TEST_ASSERT(!SubstructMatch(*mol, *query, matchV, true, true));
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, false));

    TEST_ASSERT(mol->getBondWithIdx(2)->getBondType() == Bond::DOUBLE);
    mol->getBondWithIdx(2)->getStereoAtoms().push_back(1);
    mol->getBondWithIdx(2)->getStereoAtoms().push_back(4);
    mol->getBondWithIdx(2)->setStereo(Bond::STEREOCIS);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));

    mol->getBondWithIdx(2)->setStereo(Bond::STEREOTRANS);
    TEST_ASSERT(!SubstructMatch(*mol, *query, matchV, true, true));
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, false));

    query->getBondWithIdx(1)->setStereo(Bond::STEREONONE);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));
    query->getBondWithIdx(1)->setStereo(Bond::STEREOANY);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));
    delete mol;
    delete query;
  }
  {
    std::string qSmi = "CC=CC";
    std::string mSmi = "CC=C(C)F";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));

    TEST_ASSERT(query->getBondWithIdx(1)->getBondType() == Bond::DOUBLE);
    query->getBondWithIdx(1)->getStereoAtoms().push_back(0);
    query->getBondWithIdx(1)->getStereoAtoms().push_back(3);
    query->getBondWithIdx(1)->setStereo(Bond::STEREOCIS);
    TEST_ASSERT(!SubstructMatch(*mol, *query, matchV, true, true));
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, false));

    TEST_ASSERT(mol->getBondWithIdx(1)->getBondType() == Bond::DOUBLE);
    mol->getBondWithIdx(1)->getStereoAtoms().push_back(0);
    mol->getBondWithIdx(1)->getStereoAtoms().push_back(3);
    mol->getBondWithIdx(1)->setStereo(Bond::STEREOCIS);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));

    mol->getBondWithIdx(1)->setStereo(Bond::STEREOTRANS);
    TEST_ASSERT(!SubstructMatch(*mol, *query, matchV, true, true));
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, false));

    query->getBondWithIdx(1)->setStereo(Bond::STEREONONE);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));
    query->getBondWithIdx(1)->setStereo(Bond::STEREOANY);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));
    delete mol;
    delete query;
  }
  {
    std::string qSmi = "CC=CC";
    std::string mSmi = "CCC=C(C)F";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));
    TEST_ASSERT(query->getBondWithIdx(1)->getBondType() == Bond::DOUBLE);
    query->getBondWithIdx(1)->getStereoAtoms().push_back(0);
    query->getBondWithIdx(1)->getStereoAtoms().push_back(3);
    query->getBondWithIdx(1)->setStereo(Bond::STEREOCIS);
    TEST_ASSERT(!SubstructMatch(*mol, *query, matchV, true, true));
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, false));

    TEST_ASSERT(mol->getBondWithIdx(2)->getBondType() == Bond::DOUBLE);
    mol->getBondWithIdx(2)->getStereoAtoms().push_back(1);
    mol->getBondWithIdx(2)->getStereoAtoms().push_back(4);
    mol->getBondWithIdx(2)->setStereo(Bond::STEREOCIS);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));

    mol->getBondWithIdx(2)->setStereo(Bond::STEREOTRANS);
    TEST_ASSERT(!SubstructMatch(*mol, *query, matchV, true, true));
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, false));

    query->getBondWithIdx(1)->setStereo(Bond::STEREONONE);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));
    query->getBondWithIdx(1)->setStereo(Bond::STEREOANY);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));
    delete mol;
    delete query;
  }
  {  // now make it harder: the stereoatoms don't match, but the stereochemistry
     // does
    std::string qSmi = "CC=CC";
    std::string mSmi = "CCC=C(C)F";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));

    TEST_ASSERT(query->getBondWithIdx(1)->getBondType() == Bond::DOUBLE);
    query->getBondWithIdx(1)->getStereoAtoms().push_back(0);
    query->getBondWithIdx(1)->getStereoAtoms().push_back(3);
    query->getBondWithIdx(1)->setStereo(Bond::STEREOCIS);
    TEST_ASSERT(!SubstructMatch(*mol, *query, matchV, true, true));
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, false));

    TEST_ASSERT(mol->getBondWithIdx(2)->getBondType() == Bond::DOUBLE);
    mol->getBondWithIdx(2)->getStereoAtoms().push_back(1);
    mol->getBondWithIdx(2)->getStereoAtoms().push_back(5);
    mol->getBondWithIdx(2)->setStereo(Bond::STEREOTRANS);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));

    mol->getBondWithIdx(2)->setStereo(Bond::STEREOCIS);
    TEST_ASSERT(!SubstructMatch(*mol, *query, matchV, true, true));
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, false));

    query->getBondWithIdx(1)->setStereo(Bond::STEREONONE);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));
    query->getBondWithIdx(1)->setStereo(Bond::STEREOANY);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));
    delete mol;
    delete query;
  }
  {  // now make it harder: the stereoatoms don't match on either end, but the
     // stereochemistry does
    std::string qSmi = "CC=CC";
    std::string mSmi = "CCC(F)=C(C)F";
    ROMol *query = SmilesToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));

    TEST_ASSERT(query->getBondWithIdx(1)->getBondType() == Bond::DOUBLE);
    query->getBondWithIdx(1)->getStereoAtoms().push_back(0);
    query->getBondWithIdx(1)->getStereoAtoms().push_back(3);
    query->getBondWithIdx(1)->setStereo(Bond::STEREOCIS);
    TEST_ASSERT(!SubstructMatch(*mol, *query, matchV, true, true));
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, false));

    TEST_ASSERT(mol->getBondWithIdx(3)->getBondType() == Bond::DOUBLE);
    mol->getBondWithIdx(3)->getStereoAtoms().push_back(3);
    mol->getBondWithIdx(3)->getStereoAtoms().push_back(6);
    mol->getBondWithIdx(3)->setStereo(Bond::STEREOCIS);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));

    mol->getBondWithIdx(3)->setStereo(Bond::STEREOTRANS);
    TEST_ASSERT(!SubstructMatch(*mol, *query, matchV, true, true));
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, false));

    query->getBondWithIdx(1)->setStereo(Bond::STEREONONE);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));
    query->getBondWithIdx(1)->setStereo(Bond::STEREOANY);
    TEST_ASSERT(SubstructMatch(*mol, *query, matchV, true, true));
    delete mol;
    delete query;
  }

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

void testGitHubIssue15() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test GitHub issue 15" << std::endl;

  {
    std::string qSmi = "[R2]~[R1]~[R2]";
    std::string mSmi = "CCC";
    ROMol *query = SmartsToMol(qSmi);
    ROMol *mol = SmilesToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }
  {
    std::string qSmi = "[R2]~[R1]~[R2]";
    std::string mSmi = "CCC";
    ROMol *query = SmartsToMol(qSmi);
    ROMol *mol = SmartsToMol(mSmi);
    MatchVectType matchV;
    bool matched = SubstructMatch(*mol, *query, matchV, true, true, true);
    delete mol;
    delete query;
    TEST_ASSERT(!matched);
  }

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

void testGitHubIssue409() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test GitHub issue 409" << std::endl;
  {
    std::string smi = "FC(F)(F)CC(F)(F)F";
    ROMol *mol = SmilesToMol(smi);
    std::vector<MatchVectType> matches;
    unsigned int matched =
        SubstructMatch(*mol, *mol, matches, false, true, false, false);
    TEST_ASSERT(matched == matches.size());
    TEST_ASSERT(matches.size() == 72);
    matched =
        SubstructMatch(*mol, *mol, matches, false, true, false, false, 16);
    TEST_ASSERT(matches.size() == 16);
    delete mol;
  }
  BOOST_LOG(rdErrorLog) << "  done" << std::endl;
}

void testGitHubIssue688() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test GitHub issue 688: partially specified "
                           "chiral substructure queries don't work properly"
                        << std::endl;
  {
    std::string smi = "C1CC[C@](Cl)(N)O1";
    ROMol *mol = SmilesToMol(smi);
    TEST_ASSERT(mol);
    // mol->debugMol(std::cerr);
    std::string sma = "C1CC[C@](N)O1";
    ROMol *qmol = SmartsToMol(sma);
    TEST_ASSERT(qmol);
    // qmol->updatePropertyCache();
    // qmol->debugMol(std::cerr);

    MatchVectType match;
    TEST_ASSERT(SubstructMatch(*mol, *qmol, match, true, false));
    TEST_ASSERT(match.size() == qmol->getNumAtoms());

    TEST_ASSERT(SubstructMatch(*mol, *qmol, match, true, true));
    TEST_ASSERT(match.size() == qmol->getNumAtoms());

    delete mol;
    delete qmol;
  }
  {
    std::string smi = "C1CC[C@](Cl)(N)O1";
    ROMol *mol = SmilesToMol(smi);
    TEST_ASSERT(mol);
    // mol->debugMol(std::cerr);
    std::string sma = "C1CC[C@@](N)O1";
    ROMol *qmol = SmartsToMol(sma);
    TEST_ASSERT(qmol);
    // qmol->updatePropertyCache();
    // qmol->debugMol(std::cerr);

    MatchVectType match;
    TEST_ASSERT(SubstructMatch(*mol, *qmol, match, true, false));
    TEST_ASSERT(match.size() == qmol->getNumAtoms());

    TEST_ASSERT(!SubstructMatch(*mol, *qmol, match, true, true));

    delete mol;
    delete qmol;
  }
  {
    std::string smi = "N[C@]1(Cl)CCCO1";
    ROMol *mol = SmilesToMol(smi);
    TEST_ASSERT(mol);
    // mol->debugMol(std::cerr);
    std::string sma = "N[C@]1CCCO1";
    ROMol *qmol = SmartsToMol(sma);
    TEST_ASSERT(qmol);
    // qmol->updatePropertyCache();
    // qmol->debugMol(std::cerr);
    // std::cerr << MolToSmiles(*qmol, true) << std::endl;

    MatchVectType match;
    TEST_ASSERT(SubstructMatch(*mol, *qmol, match, true, false));
    TEST_ASSERT(match.size() == qmol->getNumAtoms());

    TEST_ASSERT(SubstructMatch(*mol, *qmol, match, true, true));
    TEST_ASSERT(match.size() == qmol->getNumAtoms());

    delete mol;
    delete qmol;
  }
  {
    std::string smi = "N[C@]1(Cl)CCCO1";
    ROMol *mol = SmilesToMol(smi);
    TEST_ASSERT(mol);
    // mol->debugMol(std::cerr);
    std::string sma = "N[C@@]1CCCO1";
    ROMol *qmol = SmartsToMol(sma);
    TEST_ASSERT(qmol);
    // qmol->updatePropertyCache();
    // qmol->debugMol(std::cerr);
    // std::cerr << MolToSmiles(*qmol, true) << std::endl;

    MatchVectType match;
    TEST_ASSERT(SubstructMatch(*mol, *qmol, match, true, false));
    TEST_ASSERT(match.size() == qmol->getNumAtoms());

    TEST_ASSERT(!SubstructMatch(*mol, *qmol, match, true, true));

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

void testDativeMatch() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Test dative-bond matching" << std::endl;
  {
    std::string smi = "[Cu]->[Fe]";
    ROMol *mol = SmilesToMol(smi);
    TEST_ASSERT(mol);

    // make sure a self-match works
    MatchVectType match;
    TEST_ASSERT(SubstructMatch(*mol, *mol, match));
    TEST_ASSERT(match.size() == mol->getNumAtoms());

    {  // reverse the order and make sure that works
      std::string sma = "[Fe]<-[Cu]";
      ROMol *qmol = SmilesToMol(sma);
      TEST_ASSERT(qmol);
      MatchVectType match;
      TEST_ASSERT(SubstructMatch(*mol, *qmol, match));
      TEST_ASSERT(match.size() == qmol->getNumAtoms());
      delete qmol;
    }
    {  // reverse the direction and make sure that does not work.
      std::string sma = "[Fe]->[Cu]";
      ROMol *qmol = SmilesToMol(sma);
      TEST_ASSERT(qmol);
      MatchVectType match;
      TEST_ASSERT(!SubstructMatch(*mol, *qmol, match));
      delete qmol;
    }

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

void testGithubIssue1489() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog) << "    Testing Github #1389: Substructure matching "
                           "with chirality failure when query is built from "
                           "SMARTS"
                        << std::endl;
#if 1
  {
    std::string smi1 = "CCC[C@@H]1CN(CCC)CCN1";
    std::string smi2 = "CCC[C@H]1CN(CCC)CCN1";
    ROMol *mol1 = SmilesToMol(smi1);
    TEST_ASSERT(mol1);
    ROMol *mol2 = SmilesToMol(smi2);
    TEST_ASSERT(mol2);

    bool recursionPossible = true;
    bool useChirality = true;

    MatchVectType match;
    // make sure self-matches work
    TEST_ASSERT(
        SubstructMatch(*mol1, *mol1, match, recursionPossible, useChirality));
    TEST_ASSERT(
        SubstructMatch(*mol2, *mol2, match, recursionPossible, useChirality));

    // check matches using the molecules from smiles:
    TEST_ASSERT(
        !SubstructMatch(*mol1, *mol2, match, recursionPossible, useChirality));
    TEST_ASSERT(SubstructMatch(*mol1, *mol2, match, recursionPossible, false));

    {
      ROMol *qmol1 = SmartsToMol(smi1);

      qmol1->updatePropertyCache();
      TEST_ASSERT(qmol1);
      TEST_ASSERT(
          SubstructMatch(*mol1, *qmol1, match, recursionPossible, false));
      TEST_ASSERT(SubstructMatch(*mol1, *qmol1, match, recursionPossible,
                                 useChirality));
      TEST_ASSERT(
          SubstructMatch(*mol2, *qmol1, match, recursionPossible, false));
      TEST_ASSERT(!SubstructMatch(*mol2, *qmol1, match, recursionPossible,
                                  useChirality));
      delete qmol1;
    }
    delete mol1;
    delete mol2;
  }
#endif
  {
    std::string smi1 = "F([C@@H](Cl)Br)";
    ROMol *mol1 = SmilesToMol(smi1);
    TEST_ASSERT(mol1);

    bool recursionPossible = true;
    bool useChirality = true;

    MatchVectType match;
    // make sure self-matches work
    TEST_ASSERT(
        SubstructMatch(*mol1, *mol1, match, recursionPossible, useChirality));
    {
      ROMol *qmol1 = SmartsToMol(smi1);

      qmol1->updatePropertyCache();
      TEST_ASSERT(qmol1);
      TEST_ASSERT(
          SubstructMatch(*mol1, *qmol1, match, recursionPossible, false));
      TEST_ASSERT(SubstructMatch(*mol1, *qmol1, match, recursionPossible,
                                 useChirality));
      delete qmol1;
    }
    {
      std::string smi2 = "F([C@H](Br)Cl)";
      ROMol *qmol1 = SmartsToMol(smi2);

      qmol1->updatePropertyCache();
      TEST_ASSERT(qmol1);
      TEST_ASSERT(
          SubstructMatch(*mol1, *qmol1, match, recursionPossible, false));
      TEST_ASSERT(SubstructMatch(*mol1, *qmol1, match, recursionPossible,
                                 useChirality));
      delete qmol1;
    }
    delete mol1;
  }

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

void testGithub2570() {
  BOOST_LOG(rdInfoLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdInfoLog)
      << "Testing Github #2570: issue pointed out by Greg in the PR."
      << std::endl;

  bool uniquify = true;
  bool recursionPossible = true;
  bool useChirality = true;
  {
    const auto mol = R"(C[C@](Cl)(Br)F)"_smiles;

    {
      const auto query = R"([C@](Cl)(Br)F)"_smarts;
      std::vector<MatchVectType> matches;
      TEST_ASSERT(!SubstructMatch(*mol, *query, matches, uniquify,
                                  recursionPossible, useChirality));
    }
    {
      const auto query = R"([C@@](Cl)(Br)F)"_smarts;
      std::vector<MatchVectType> matches;
      TEST_ASSERT(SubstructMatch(*mol, *query, matches, uniquify,
                                 recursionPossible, useChirality));
    }
    {  // Swap order of a pair of atoms
      const auto query = R"([C@](Br)(Cl)F)"_smarts;
      std::vector<MatchVectType> matches;
      TEST_ASSERT(SubstructMatch(*mol, *query, matches, uniquify,
                                 recursionPossible, useChirality));
    }
    {
      const auto query = R"([C@@](Br)(Cl)F)"_smarts;
      std::vector<MatchVectType> matches;
      TEST_ASSERT(!SubstructMatch(*mol, *query, matches, uniquify,
                                  recursionPossible, useChirality));
    }
    {  // Smaller fragments should always match as long as they have have a
       // chiral tag,
      // as these don't have enough neighbors to define CW/CCW chirality
      const std::vector<std::string> smarts({"[C@](Cl)Br", "[C@@](Cl)Br",
                                             "[C@](Br)F", "[C@@](Br)F", "[C@]F",
                                             "[C@@]F", "[C@]", "[C@@]"});
      std::vector<MatchVectType> matches;
      for (const auto &sma : smarts) {
        std::unique_ptr<ROMol> query(SmartsToMol(sma));
        TEST_ASSERT(SubstructMatch(*mol, *query, matches, uniquify,
                                   recursionPossible, useChirality));
      }
    }
  }
  {  // Mol also starting with the chiral atom
    const auto mol = R"([C@](C)(Cl)(Br)F)"_smiles;
    {
      const auto query = R"([C@](C)(Cl)(Br)F)"_smarts;
      std::vector<MatchVectType> matches;
      TEST_ASSERT(SubstructMatch(*mol, *query, matches, uniquify,
                                 recursionPossible, useChirality));
    }
    {
      const auto query = R"([C@@](C)(Cl)(Br)F)"_smarts;
      std::vector<MatchVectType> matches;
      TEST_ASSERT(!SubstructMatch(*mol, *query, matches, uniquify,
                                  recursionPossible, useChirality));
    }
    {
      const auto query = R"([C@](C)(Cl)Br)"_smarts;
      std::vector<MatchVectType> matches;
      TEST_ASSERT(SubstructMatch(*mol, *query, matches, uniquify,
                                 recursionPossible, useChirality));
    }
    {
      const auto query = R"([C@@](C)(Cl)Br)"_smarts;
      std::vector<MatchVectType> matches;
      TEST_ASSERT(!SubstructMatch(*mol, *query, matches, uniquify,
                                  recursionPossible, useChirality));
    }
    {
      const auto query = R"([C@](Cl)(Br)F)"_smarts;
      std::vector<MatchVectType> matches;
      TEST_ASSERT(!SubstructMatch(*mol, *query, matches, uniquify,
                                  recursionPossible, useChirality));
    }
    {
      const auto query = R"([C@@](Cl)(Br)F)"_smarts;
      std::vector<MatchVectType> matches;
      TEST_ASSERT(SubstructMatch(*mol, *query, matches, uniquify,
                                 recursionPossible, useChirality));
    }
    {  // Swap order of a pair of atoms
      const auto query = R"([C@](Br)(Cl)F)"_smarts;
      std::vector<MatchVectType> matches;
      TEST_ASSERT(SubstructMatch(*mol, *query, matches, uniquify,
                                 recursionPossible, useChirality));
    }
    {
      const auto query = R"([C@@](Br)(Cl)F)"_smarts;
      std::vector<MatchVectType> matches;
      TEST_ASSERT(!SubstructMatch(*mol, *query, matches, uniquify,
                                  recursionPossible, useChirality));
    }
  }

  {  // Start from a physical H atom
    const auto mol = R"([H][C@](O)(F)Cl)"_smiles;
    const auto smarts = MolToSmarts(*mol);
    std::unique_ptr<ROMol> query(SmartsToMol(smarts));
    TEST_ASSERT(smarts == R"([#8]-[#6@@H](-[#9])-[#17])");
    std::vector<MatchVectType> matches;
    TEST_ASSERT(SubstructMatch(*mol, *query, matches, uniquify,
                               recursionPossible, useChirality));
  }
  {
    const auto mol = R"([H][C@](O)(F)Cl)"_smiles;
    const auto query = R"([C@H](O)(F)Cl)"_smarts;
    std::vector<MatchVectType> matches;
    TEST_ASSERT(!SubstructMatch(*mol, *query, matches, uniquify,
                                recursionPossible, useChirality));
  }
  {  // Start from an attached H atom
    const auto mol = R"([C@H](O)(F)Cl)"_smiles;
    const auto smarts = MolToSmarts(*mol);
    TEST_ASSERT(smarts == R"([#8]-[#6@@H](-[#9])-[#17])");
    const auto query = SmartsToMol(smarts);
    std::vector<MatchVectType> matches;
    TEST_ASSERT(SubstructMatch(*mol, *query, matches, uniquify,
                               recursionPossible, useChirality));
    delete query;
  }
  {
    const auto mol = R"([C@H](O)(F)Cl)"_smiles;
    const auto query = R"([C@H](O)(F)Cl)"_smarts;
    std::vector<MatchVectType> matches;
    TEST_ASSERT(!SubstructMatch(*mol, *query, matches, uniquify,
                                recursionPossible, useChirality));
  }
  {  // Without H
    const auto mol = R"([C@](O)(F)(Cl)C)"_smiles;
    const auto smarts = MolToSmarts(*mol);
    const auto query = SmartsToMol(smarts);
    TEST_ASSERT(smarts == R"([#8]-[#6@](-[#9])(-[#17])-[#6])");
    std::vector<MatchVectType> matches;
    TEST_ASSERT(SubstructMatch(*mol, *query, matches, uniquify,
                               recursionPossible, useChirality));
    delete query;
  }
  {
    const auto mol = R"([C@](O)(F)(Cl)C)"_smiles;
    const auto query = R"([#6@](-[#8])(-[#9])(-[#17])-[#6])"_smarts;
    std::vector<MatchVectType> matches;
    TEST_ASSERT(SubstructMatch(*mol, *query, matches, uniquify,
                               recursionPossible, useChirality));
  }

  {  // What about queries not coming from SMARTS?
    const std::vector<std::string> smiles(  // These are all equivalent
        {"N[C@@]([H])(C)C(=O)O", "N[C@@H](C)C(=O)O", "N[C@H](C(=O)O)C",
         "[H][C@](N)(C)C(=O)O", "[C@H](N)(C)C(=O)O"});
    for (const auto &smi1 : smiles) {
      const auto mol1 = std::unique_ptr<ROMol>(SmilesToMol(smi1));
      for (const auto &smi2 : smiles) {  // Test them in both directions
        const auto mol2 = std::unique_ptr<ROMol>(SmilesToMol(smi2));
        std::vector<MatchVectType> matches;
        TEST_ASSERT(SubstructMatch(*mol1, *mol2, matches, uniquify,
                                   recursionPossible, useChirality));
      };
    }
  }

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

void testEZVsCisTransMatch() {
  BOOST_LOG(rdErrorLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdErrorLog)
      << "    Testing matching E/Z against Cis/Trans stereo bonds" << std::endl;

  const auto mol = R"(F/C(C)=C(C)/Cl)"_smiles;
  {
    const Bond *stereoBnd = mol->getBondWithIdx(2);
    TEST_ASSERT(stereoBnd->getStereo() == Bond::STEREOE);
  }

  // pairs of {query, matching expectation}
  const std::vector<std::pair<std::string, bool>> checks({
      {R"(F/C(C)=C(C)/Cl)", true},   // identical
      {R"(F\C(C)=C(C)\Cl)", true},   // symmetric
      {R"(F/C(C)=C(C)\Cl)", false},  // opposite
      {R"(F\C(C)=C(C)/Cl)", false}   // symmetric opposite
  });

  // Test with same stereoatoms as mol
  for (const auto &check : checks) {
    auto query = SmilesToMol(check.first);
    {
      Bond *stereoBnd = query->getBondWithIdx(2);
      auto stereo = stereoBnd->getStereo();
      TEST_ASSERT(stereo == Bond::STEREOE || stereo == Bond::STEREOZ);

      stereoBnd->setStereoAtoms(0, 5);  // Same as mol
      stereo = Chirality::translateEZLabelToCisTrans(stereo);
      TEST_ASSERT(stereo == Bond::STEREOCIS || stereo == Bond::STEREOTRANS);
      stereoBnd->setStereo(stereo);
    }
    MatchVectType match;
    bool recursionPossible = true;
    bool useChirality = true;
    TEST_ASSERT(check.second == SubstructMatch(*mol, *query, match,
                                               recursionPossible,
                                               useChirality));
    delete query;
  }
  // Symmetrize stereoatoms
  for (const auto &check : checks) {
    auto query = SmilesToMol(check.first);
    {
      Bond *stereoBnd = query->getBondWithIdx(2);
      auto stereo = stereoBnd->getStereo();
      TEST_ASSERT(stereo == Bond::STEREOE || stereo == Bond::STEREOZ);

      stereoBnd->setStereoAtoms(2, 4);  // symmetric to mol
      stereo = Chirality::translateEZLabelToCisTrans(stereo);
      TEST_ASSERT(stereo == Bond::STEREOCIS || stereo == Bond::STEREOTRANS);
      stereoBnd->setStereo(stereo);
    }
    MatchVectType match;
    bool recursionPossible = true;
    bool useChirality = true;
    TEST_ASSERT(check.second == SubstructMatch(*mol, *query, match,
                                               recursionPossible,
                                               useChirality));
    delete query;
  }
  // Flip one stereoatom and the label
  for (const auto &check : checks) {
    auto query = SmilesToMol(check.first);
    {
      Bond *stereoBnd = query->getBondWithIdx(2);
      auto stereo = stereoBnd->getStereo();
      TEST_ASSERT(stereo == Bond::STEREOE || stereo == Bond::STEREOZ);

      stereoBnd->setStereoAtoms(0, 4);  // Reverse second stereoatom
      if (stereo == Bond::STEREOE) {
        stereo = Bond::STEREOCIS;
      } else {
        stereo = Bond::STEREOTRANS;
      }
      stereoBnd->setStereo(stereo);
    }
    MatchVectType match;
    bool recursionPossible = true;
    bool useChirality = true;
    TEST_ASSERT(check.second == SubstructMatch(*mol, *query, match,
                                               recursionPossible,
                                               useChirality));
    delete query;
  }
}

void testMostSubstitutedCoreMatch() {
  BOOST_LOG(rdInfoLog) << "-------------------------------------" << std::endl;
  BOOST_LOG(rdInfoLog) << "Testing getMostSubstitutedCoreMatch and "
                          "sortMatchesByDegreeOfCoreSubstitution"
                       << std::endl;
  auto core = "[*:1]c1cc([*:2])ccc1[*:3]"_smarts;
  auto orthoMeta = "c1ccc(-c2ccc(-c3ccccc3)c(-c3ccccc3)c2)cc1"_smiles;
  auto ortho = "c1ccc(-c2ccccc2-c2ccccc2)cc1"_smiles;
  auto meta = "c1ccc(-c2cccc(-c3ccccc3)c2)cc1"_smiles;
  auto biphenyl = "c1ccccc1-c1ccccc1"_smiles;
  auto phenyl = "c1ccccc1"_smiles;

  struct numHsMatchingDummies {
    static unsigned int get(const ROMol &mol, const ROMol &core,
                            const MatchVectType &match) {
      return std::count_if(
          match.begin(), match.end(),
          [&mol, &core](const std::pair<int, int> &pair) {
            return (core.getAtomWithIdx(pair.first)->getAtomicNum() == 0 &&
                    mol.getAtomWithIdx(pair.second)->getAtomicNum() == 1);
          });
    }
  };

  const auto &coreRef = *core;
  for (auto &molResPair :
       {std::make_pair(orthoMeta.get(), 0u), std::make_pair(ortho.get(), 1u),
        std::make_pair(meta.get(), 1u), std::make_pair(biphenyl.get(), 2u),
        std::make_pair(phenyl.get(), 3u)}) {
    auto &mol = *molResPair.first;
    const auto res = molResPair.second;
    MolOps::addHs(mol);
    auto matches = SubstructMatch(mol, coreRef);
    auto bestMatch = getMostSubstitutedCoreMatch(mol, coreRef, matches);
    TEST_ASSERT(numHsMatchingDummies::get(mol, coreRef, bestMatch) == res);
    std::vector<unsigned int> ctrlCounts(matches.size());
    std::transform(matches.begin(), matches.end(), ctrlCounts.begin(),
                   [&mol, &coreRef](const MatchVectType &match) {
                     return numHsMatchingDummies::get(mol, coreRef, match);
                   });
    std::sort(ctrlCounts.begin(), ctrlCounts.end());
    std::vector<unsigned int> sortedCounts(matches.size());
    auto sortedMatches =
        sortMatchesByDegreeOfCoreSubstitution(mol, coreRef, matches);
    std::transform(sortedMatches.begin(), sortedMatches.end(),
                   sortedCounts.begin(),
                   [&mol, &coreRef](const MatchVectType &match) {
                     return numHsMatchingDummies::get(mol, coreRef, match);
                   });
    TEST_ASSERT(ctrlCounts == sortedCounts);
  }
  std::vector<MatchVectType> emptyMatches;
  bool raised = false;
  try {
    getMostSubstitutedCoreMatch(*orthoMeta, coreRef, emptyMatches);
  } catch (const Invar::Invariant &) {
    raised = true;
  }
  TEST_ASSERT(raised);
  raised = false;
  try {
    sortMatchesByDegreeOfCoreSubstitution(*orthoMeta, coreRef, emptyMatches);
  } catch (const Invar::Invariant &) {
    raised = true;
  }
  TEST_ASSERT(raised);
}

int main(int argc, char *argv[]) {
  RDLog::InitLogs();
  test1();
  test2();
  test3();
  test4();
  test5();
  test5QueryRoot();
  test6();
  if (argc > 1 && !strcmp(argv[1], "-l")) {
    test7();
  }
  // test9();
  testRecursiveSerialNumbers();
  testMultiThread();
  testGitHubIssue15();
  testGitHubIssue409();
  testChiralMatch();
  testGitHubIssue688();
  testDativeMatch();
  testCisTransMatch();
  testCisTransMatch2();
  testGithubIssue1489();
  testGithub2570();
  testEZVsCisTransMatch();
  testMostSubstitutedCoreMatch();

  return 0;
}