rdkit/Code/GraphMol/ChemTransforms/catch_tests.cpp

//
//  Copyright (c) 2019-2025 Greg Landrum and other RDKit contributors
//
//   @@ 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 <catch2/catch_all.hpp>

#include <GraphMol/RDKitBase.h>
#include <GraphMol/test_fixtures.h>
#include <GraphMol/SmilesParse/SmilesParse.h>
#include <GraphMol/SmilesParse/SmilesWrite.h>
#include <GraphMol/ChemTransforms/ChemTransforms.h>
#include <GraphMol/FileParsers/FileParsers.h>
#include <GraphMol/FileParsers/MolSupplier.h>
#include <GraphMol/Substruct/SubstructMatch.h>

#include <algorithm>
#include <regex>

using namespace RDKit;
using std::unique_ptr;

TEST_CASE("Github #1039") {
  const auto useLegacy = GENERATE(true, false);
  UseLegacyStereoPerceptionFixture fx(useLegacy);
  SECTION("double bond") {
    auto m1 = "C/C=C/C=C/C"_smiles;
    REQUIRE(m1);
    std::vector<unsigned int> bonds = {2};
    std::unique_ptr<ROMol> pieces(MolFragmenter::fragmentOnBonds(*m1, bonds));
    REQUIRE(pieces);
    CHECK(pieces->getNumAtoms() == 8);
    REQUIRE(pieces->getBondBetweenAtoms(3, 6));
    REQUIRE(pieces->getBondBetweenAtoms(2, 7));
    CHECK(pieces->getBondBetweenAtoms(3, 6)->getBondType() == Bond::SINGLE);
    CHECK(pieces->getBondBetweenAtoms(3, 6)->getBondDir() == Bond::ENDUPRIGHT);
    CHECK(pieces->getBondBetweenAtoms(2, 7)->getBondType() == Bond::SINGLE);
    CHECK(pieces->getBondBetweenAtoms(2, 7)->getBondDir() == Bond::ENDUPRIGHT);
    CHECK(MolToSmiles(*pieces) == "[2*]/C=C/C.[3*]/C=C/C");
  }
  SECTION("atomic stereo") {
    auto m1 = "C(C)(F)(Cl)O"_smiles;
    REQUIRE(m1);
    m1->getBondWithIdx(0)->setBondDir(Bond::BEGINWEDGE);
    std::vector<unsigned int> bonds = {0};
    std::unique_ptr<ROMol> pieces(MolFragmenter::fragmentOnBonds(*m1, bonds));
    REQUIRE(pieces);
    CHECK(pieces->getNumAtoms() == 7);
    REQUIRE(pieces->getBondBetweenAtoms(0, 6));
    REQUIRE(pieces->getBondBetweenAtoms(1, 5));
    CHECK(pieces->getBondBetweenAtoms(0, 6)->getBondDir() == Bond::BEGINWEDGE);
    CHECK(pieces->getBondBetweenAtoms(1, 5)->getBondDir() == Bond::NONE);
    // no actual stereo in the SMILES here since we haven't assigned it (need a
    // conformer to do that using wedging)
    CHECK(MolToSmiles(*pieces) == "*C.[1*]C(O)(F)Cl");
  }
  SECTION("bond stereo") {
    auto m = "O/C=N/C=C"_smiles;
    std::vector<std::pair<unsigned int, unsigned int>> dummyLabels{{1, 1}};
    std::vector<unsigned int> bonds{0};
    auto resa = RDKit::MolFragmenter::fragmentOnBonds(*m, bonds);
    CHECK(MolToSmiles(*resa) == "*/C=N/C=C.[1*]O");
    // make sure we still have stereo atoms
    std::vector<std::vector<int>> expected_stereo_atoms{
        {5, 3},  // 5 is the new dummy atom, it was 0 before
        {},     {}, {}, {},
    };
    std::vector<std::vector<int>> received_stereo;
    for (auto *bond : resa->bonds()) {
      received_stereo.push_back(bond->getStereoAtoms());
    }
    CHECK(received_stereo == expected_stereo_atoms);
    delete resa;
  }
  {  // break non stereo atom bond
    auto m = "C/C(O)=N/C=C"_smiles;
    std::vector<std::pair<unsigned int, unsigned int>> dummyLabels{{1, 1}};
    std::vector<unsigned int> bonds{0};
    auto resa = RDKit::MolFragmenter::fragmentOnBonds(*m, bonds);
    CHECK(MolToSmiles(*resa) == "*/C(O)=N/C=C.[1*]C");
    // make sure we still have stereo atoms
    std::vector<std::vector<int>> expected_stereo_atoms;
    if (useLegacy) {
      expected_stereo_atoms = {{}, {2, 4}, {}, {}, {}, {}};
    } else {
      expected_stereo_atoms = {{}, {6, 4}, {}, {}, {}, {}};
    }
    std::vector<std::vector<int>> received_stereo;
    for (auto *bond : resa->bonds()) {
      received_stereo.push_back(bond->getStereoAtoms());
    }
    CHECK(received_stereo == expected_stereo_atoms);
    delete resa;
  }
  {  // bond stereo should only be removed when deleting the double bond with
     // E/Z
    auto m = "O/C=N/C=C"_smiles;
    std::vector<std::pair<unsigned int, unsigned int>> dummyLabels{{1, 1}};
    std::vector<std::string> expected = {
        "*/C=N/C=C.[1*]O",
        "[1*]=NC=C.[2*]=CO",  // bond stereo gone
        "[2*]C=C.[3*]/N=C/O", "[3*]=C.[4*]=C/N=C/O"};
    for (unsigned int i = 0; i < m->getNumBonds(); ++i) {
      std::vector<unsigned int> bonds{i};
      auto resa = RDKit::MolFragmenter::fragmentOnBonds(*m, bonds);
      auto smiles = MolToSmiles(*resa);
      CHECK(smiles == expected[i]);
      delete resa;
    }
  }
  {  // bond stereo should only be removed when deleting the double bond with
     // E/Z
    // chiral stereo should stay
    auto m = "O/C=N/[C@H](I)F"_smiles;
    std::vector<std::pair<unsigned int, unsigned int>> dummyLabels{{1, 1}};
    std::vector<std::string> expected = {
        "*/C=N/[C@@H](F)I.[1*]O",
        "[1*]=N[C@@H](F)I.[2*]=CO",  // bond stereo gone
        "[2*][C@@H](F)I.[3*]/N=C/O", "[3*]I.[4*][C@H](F)/N=C/O",
        "[3*]F.[5*][C@@H](I)/N=C/O"};
    for (unsigned int i = 0; i < m->getNumBonds(); ++i) {
      std::vector<unsigned int> bonds{i};
      auto resa = RDKit::MolFragmenter::fragmentOnBonds(*m, bonds);
      auto smiles = MolToSmiles(*resa);
      CHECK(smiles == expected[i]);
      delete resa;
    }
  }
}

TEST_CASE("molzip") {
  const auto useLegacy = GENERATE(true, false);
  CAPTURE(useLegacy);
  UseLegacyStereoPerceptionFixture fx(useLegacy);
  SECTION("basic tests") {
    {
      auto a = "C[*:1]"_smiles;
      auto b = "N[*:1]"_smiles;
      auto mol = molzip(*a, *b);
      CHECK(MolToSmiles(*mol) == "CN");
    }
    {
      // 0 isotopes aren't mapped
      auto a = "C[*]"_smiles;
      auto b = "N[*]"_smiles;
      MolzipParams p;
      auto mol = molzip(*a, *b, p);
      CHECK(MolToSmiles(*mol) == "*C.*N");
    }
    {
      auto a = "C[1*]"_smiles;
      auto b = "N[1*]"_smiles;
      MolzipParams p;
      p.label = MolzipLabel::Isotope;
      auto mol = molzip(*a, *b, p);
      CHECK(MolToSmiles(*mol) == "CN");
    }
    {
      auto a = "[C@H](Br)([*:1])F"_smiles;
      auto b = "[*:1]N"_smiles;
      auto mol = molzip(*a, *b);
      CHECK(MolToSmiles(*mol) == "N[C@@H](F)Br");
    }
    {
      auto a = "[C@H]([*:1])(Br)F"_smiles;
      auto b = "[*:1]N"_smiles;
      auto mol = molzip(*a, *b);
      CHECK(MolToSmiles(*mol) == "N[C@H](F)Br");
    }

    {
      auto a = "[C@H]([*:1])(F)([*:2])"_smiles;
      auto b = "[*:1]N.[*:2]I"_smiles;
      auto mol = molzip(*a, *b);
      REQUIRE(MolToSmiles(*mol) == "N[C@@H](F)I");
    }

    {
      auto a = "[C@H]([Xe])(F)([V])"_smiles;
      auto b = "[Xe]N.[V]I"_smiles;
      MolzipParams params;
      params.label = MolzipLabel::AtomType;
      params.atomSymbols = {"Xe", "V"};
      auto mol = molzip(*a, *b, params);
      CHECK(MolToSmiles(*mol) == "N[C@@H](F)I");
    }

    {
      auto m = "OOO[C@](F)(I)N"_smiles;
      std::vector<std::pair<unsigned int, unsigned int>> dummyLabels{{1, 1},
                                                                     {2, 2}};
      for (unsigned int i = 0; i < m->getNumBonds(); ++i) {
        for (unsigned int j = 0; j < m->getNumBonds(); ++j) {
          if (i != j) {
            std::vector<unsigned int> bonds{i, j};
            auto resa = RDKit::MolFragmenter::fragmentOnBonds(*m, bonds);
            MolzipParams p;
            p.label = MolzipLabel::FragmentOnBonds;
            CHECK(MolToSmiles(*molzip(*resa, p)) == MolToSmiles(*m));
            delete resa;
            // Now try using atom labels
            auto res = RDKit::MolFragmenter::fragmentOnBonds(*m, bonds, true,
                                                             &dummyLabels);
            for (auto *atom : res->atoms()) {
              if (atom->getIsotope()) {
                atom->setAtomMapNum(atom->getIsotope());
              }
            }
            CHECK(MolToSmiles(*molzip(*res)) == MolToSmiles(*m));
            delete res;
          }
        }
      }
    }
  }
  SECTION("use atom property as label") {
    auto a = "[C@H]([*])(F)([*])"_smiles;
    auto b = "[*]N.[*]I"_smiles;
    a->getAtomWithIdx(1)->setProp<unsigned int>("foo", 1);
    a->getAtomWithIdx(3)->setProp<unsigned int>("foo", 2);
    b->getAtomWithIdx(0)->setProp<unsigned int>("foo", 1);
    b->getAtomWithIdx(2)->setProp<unsigned int>("foo", 2);
    MolzipParams p;
    p.label = MolzipLabel::AtomProperty;
    p.atomProperty = "foo";
    auto mol = molzip(*a, *b, p);
    // chirality is "lost" here because [C@H]([*])(F)([*]) is considered
    // achiral
    CHECK(MolToSmiles(*mol) == "NC(F)I");
  }

  SECTION("test bond stereo") {
    {
      auto a = "F/C=C/[*:1]"_smiles;
      auto b = "[*:1]F"_smiles;
      auto mol = molzip(*a, *b);
      CHECK(MolToSmiles(*mol) == "F/C=C/F");
    }

    {
      auto a = "C=C/N=C/[*:1]"_smiles;
      auto b = "O[*:1]"_smiles;
      auto mol = molzip(*a, *b);
      CHECK(MolToSmiles(*mol) == "C=C/N=C/O");
    }

    {
      auto a = "C=C[*:1].O/C=N/[*:1]"_smiles;
      auto mol = molzip(*a);
      CHECK(MolToSmiles(*mol) == "C=C/N=C/O");
    }
    {  // test single mol isotope labels
      auto a = "C=C[1*].O/C=N/[1*]"_smiles;
      MolzipParams p;
      p.label = MolzipLabel::Isotope;
      auto mol = molzip(*a, p);
      CHECK(MolToSmiles(*mol) == "C=C/N=C/O");
    }
    {
      // double bondd stereo not handled
      // auto m =  "O/C=N/C=C/F"_smiles;
      auto m = "O/C=N/C=C"_smiles;
      std::vector<std::pair<unsigned int, unsigned int>> dummyLabels{{1, 1}};
      for (unsigned int i = 0; i < m->getNumBonds(); ++i) {
        std::vector<unsigned int> bonds{i};
        {
          std::unique_ptr<ROMol> resa{
              RDKit::MolFragmenter::fragmentOnBonds(*m, bonds)};
          auto smiles = MolToSmiles(*resa);
          if (std::count(smiles.begin(), smiles.end(), '/') != 2) {
            continue;  // we removed bond stereo in fragment to bonds!
          }
          MolzipParams p;
          p.label = MolzipLabel::FragmentOnBonds;
          CHECK(MolToSmiles(*molzip(*resa, p)) == MolToSmiles(*m));
        }
        {
          // Now try using atom labels
          std::unique_ptr<ROMol> res{RDKit::MolFragmenter::fragmentOnBonds(
              *m, bonds, true, &dummyLabels)};
          auto smiles = MolToSmiles(*res);

          if (std::count(smiles.begin(), smiles.end(), '/') != 2) {
            continue;  // we removed bond stereo in fragment to bonds!
          }
          for (auto *atom : res->atoms()) {
            if (atom->getIsotope()) {
              atom->setAtomMapNum(atom->getIsotope());
            }
          }

          CHECK(MolToSmiles(*molzip(*res)) == MolToSmiles(*m));
        }
      }
    }
  }
  SECTION("unzippable molecules") {
    auto a = "C[*:1]"_smiles;
    auto b = "N[*:2]"_smiles;
    auto mol = molzip(*a, *b);
    CHECK(MolToSmiles(*mol) == "C[*:1].N[*:2]");
  }
  {
    auto a = "[*:2]OC[*:1]"_smiles;
    auto b = "N[*:1]"_smiles;
    auto mol = molzip(*a, *b);
    CHECK(MolToSmiles(*mol) == "NCO[*:2]");
  }
  {
    auto a = "[*:1]OC[*:1]"_smiles;
    auto b = "N[*:1]"_smiles;
    bool caught = false;
    try {
      auto mol = molzip(*a, *b);
    } catch (Invar::Invariant &e) {
      CHECK(e.toUserString().find(
                "molzip: bond info already exists for end atom with label:1") !=
            std::string::npos);
      caught = true;
    }
    CHECK(caught == true);
  }

  {
    // check to see we can make a non sanitizable zipped mol
    MolzipParams p;
    p.enforceValenceRules = false;
    auto a = "CC(=[*:1])N"_smiles;
    auto b = "[*:1]-N=C"_smiles;
    auto mol = molzip(*a, *b, p);
  }

  {
    // check atom property zipping
    auto a = "C=C*.O/C=N/*"_smiles;
    a->getAtomWithIdx(2)->setProp<unsigned int>("fuse", 1);
    a->getAtomWithIdx(6)->setProp<unsigned int>("fuse", 1);
    MolzipParams p;
    p.atomProperty = "fuse";
    p.label = MolzipLabel::AtomProperty;
    auto mol = molzip(*a, p);
    CHECK(MolToSmiles(*mol) == "C=C/N=C/O");
  }

  SECTION("MolZip saves bonddir") {
    {  // a-* b<*
      auto a = "CC[*:1]"_smiles;
      auto b = "N[*:1]"_smiles;
      b->getBondWithIdx(0)->setBondDir(Bond::BondDir::BEGINWEDGE);
      auto mol = molzip(*a, *b);
      CHECK(MolToSmiles(*mol) == "CCN");
      CHECK(mol->getBondWithIdx(1)->getBondDir() == Bond::BondDir::BEGINWEDGE);
      CHECK(mol->getBondWithIdx(1)->getBeginAtom()->getIdx() == 2);
    }
    {  // a>* b-*
      auto a = "[*:1]CC"_smiles;
      auto b = "N[*:1]"_smiles;
      a->getBondWithIdx(0)->setBondDir(Bond::BondDir::BEGINWEDGE);
      auto mol = molzip(*a, *b);
      CHECK(MolToSmiles(*mol) == "CCN");
      CHECK(mol->getBondWithIdx(1)->getBondDir() == Bond::BondDir::BEGINWEDGE);
      CHECK(mol->getBondWithIdx(1)->getBeginAtom()->getIdx() == 2);
    }
    {  // a<* b-*
      auto a = "CC[*:1]"_smiles;
      auto b = "N[*:1]"_smiles;
      a->getBondWithIdx(1)->setBondDir(Bond::BondDir::BEGINWEDGE);
      auto mol = molzip(*a, *b);
      CHECK(MolToSmiles(*mol) == "CCN");
      CHECK(mol->getBondWithIdx(1)->getBondDir() == Bond::BondDir::BEGINWEDGE);
      CHECK(mol->getBondWithIdx(1)->getBeginAtom()->getIdx() == 1);
    }
    {  // a>* b-*
      auto a = "[*:1]CC"_smiles;
      auto b = "N[*:1]"_smiles;
      a->getBondWithIdx(0)->setBondDir(Bond::BondDir::BEGINWEDGE);
      auto mol = molzip(*a, *b);
      CHECK(MolToSmiles(*mol) == "CCN");
      CHECK(mol->getBondWithIdx(1)->getBondDir() == Bond::BondDir::BEGINWEDGE);
      CHECK(mol->getBondWithIdx(1)->getBeginAtom()->getIdx() == 2);
    }
    {  // a-* b<*
      auto a = "CC[*:1]"_smiles;
      auto b = "[*:1]N"_smiles;
      b->getBondWithIdx(0)->setBondDir(Bond::BondDir::BEGINWEDGE);
      auto mol = molzip(*a, *b);
      CHECK(MolToSmiles(*mol) == "CCN");
      CHECK(mol->getBondWithIdx(1)->getBondDir() == Bond::BondDir::BEGINWEDGE);
      CHECK(mol->getBondWithIdx(1)->getBeginAtom()->getIdx() == 1);
    }
  }
}

TEST_CASE(
    "Github4825: ReplaceCore should set stereo on ring bonds when it breaks "
    "rings") {
  SECTION("basics") {
    auto m = "C1C=CCC2=C1C=CC=N2"_smiles;
    REQUIRE(m);
    auto core = "c1ncccc1"_smiles;
    REQUIRE(core);
    std::unique_ptr<ROMol> res{replaceCore(*m, *core)};
    REQUIRE(res);
    auto mb = MolToV3KMolBlock(*res);
    CHECK(mb.find("CFG=2") == std::string::npos);
  }
  SECTION("adjacent") {
    auto m = "C1CC2=C(C=C1)C=CC=N2"_smiles;
    REQUIRE(m);
    auto core = "c1ncccc1"_smiles;
    REQUIRE(core);
    std::unique_ptr<ROMol> res{replaceCore(*m, *core)};
    REQUIRE(res);
    auto mb = MolToV3KMolBlock(*res);
    CHECK(mb.find("CFG=2") == std::string::npos);
  }
  SECTION("don't do larger rings") {
    auto m = "C1C=CCCCC2=C1C=CC=N2"_smiles;
    REQUIRE(m);
    auto core = "c1ncccc1"_smiles;
    REQUIRE(core);
    std::unique_ptr<ROMol> res{replaceCore(*m, *core)};
    REQUIRE(res);
    auto mb = MolToV3KMolBlock(*res);
    CHECK(mb.find("CFG=2") != std::string::npos);
  }
}

TEST_CASE(
    "Github5334: ReplaceCore should set stereo on ring bonds when it breaks "
    "rings") {
  SECTION("segfault") {
    auto a = "C([*:1])[*:2].[C@@H](Cl)([1*:1])[2*:2]"_smiles;
    bool caught = false;
    try {
      auto mol = molzip(*a);
      CHECK(false);
    } catch (Invar::Invariant &e) {
      CHECK(
          e.toUserString().find(
              "molzip: zipped Bond already exists, perhaps labels are duplicated") !=
          std::string::npos);
      caught = true;
    }
    CHECK(caught);
  }
}

TEST_CASE(
    "ReplaceCore handles chiral center with multiple bonds from core to chiral center") {
  auto structure = "C1CSCN[C@@]12(NCCCO2)"_smiles;
  auto core = "NCSCC"_smarts;
  std::unique_ptr<ROMol> res{replaceCore(*structure, *core, true, true)};
  REQUIRE(res);
  auto resultSmiles = MolToSmiles(*res);
  REQUIRE(resultSmiles == "*[C@]1([4*])NCCCO1");
}

TEST_CASE("Molzip with 2D coordinates", "[molzip]") {
  std::vector<std::string> frags = {"c1nc([1*:1])c([2*:2])c([3*:3])n1",
                                    "CC(C)(C#N)c1ccc([1*:1])cc1",
                                    "Nc1ccc(C#C[2*:2])cn1", "OCC[3*:3]"};
  std::vector<ROMOL_SPTR> mols = {
      ROMOL_SPTR(SmilesToMol(frags[0])), ROMOL_SPTR(SmilesToMol(frags[1])),
      ROMOL_SPTR(SmilesToMol(frags[2])), ROMOL_SPTR(SmilesToMol(frags[3]))};
  MolzipParams params;
  params.generateCoordinates = true;
  const auto zippedMol = molzip(mols, params);
  for (auto &mol : mols) {
    for (auto &atom : mol->atoms()) {
      atom->setIsotope(0);
      atom->setAtomMapNum(0);
    }
  }
  const auto &zippedConformer = zippedMol->getConformer();
  for (size_t i = 0; i < frags.size(); i++) {
    const auto sma =
        std::regex_replace(frags[i], std::regex(R"(\[\d\*\:\d\])"), "*");
    const auto query = SmartsToMol(sma);
    const auto &mol = mols[i];
    const auto &molConformer = mol->getConformer();
    const auto molMatches = SubstructMatch(*mol, *query);
    const auto zippedMatches = SubstructMatch(*zippedMol, *query);
    REQUIRE(molMatches.size() == 1);
    REQUIRE(zippedMatches.size() == 1);
    const auto molMatch = molMatches[0];
    const auto zippedMatch = zippedMatches[0];
    for (size_t j = 0; j < molMatch.size(); j++) {
      const auto &position1 = molConformer.getAtomPos(molMatch[i].second);
      const auto &position2 = zippedConformer.getAtomPos(zippedMatch[i].second);
      CHECK(position1.x == position2.x);
      CHECK(position1.y == position2.y);
      CHECK(position1.z == position2.z);
    }
    delete query;
  }
}

TEST_CASE("Molzip with split rings from rgroup", "[molzip]") {
  std::vector<std::string> frags = {"[*:1]CC[*:2]", "[*:1]NN[*:2]",
                                    "[*:1]NN[*:2]"};
  std::vector<ROMOL_SPTR> mols;
  for (auto smi : frags) {
    mols.push_back(ROMOL_SPTR(SmilesToMol(smi)));
  }
  const auto zippedMol = molzip(mols);
  CHECK(MolToSmiles(*zippedMol) == "C1CNN1");
}

TEST_CASE("Github #6034: FragmentOnBonds may create unexpected radicals") {
  auto m = "C[C@H](Cl)c1ccccc1"_smiles;

  REQUIRE(m);
  REQUIRE(m->getNumAtoms() == 9);

  REQUIRE(m->getAtomWithIdx(1)->getNoImplicit() == true);

  bool add_dummies = false;
  std::vector<unsigned int> bonds = {0};
  std::vector<std::pair<unsigned, unsigned>> *dummyLabels = nullptr;
  const std::vector<Bond::BondType> *bondTypes = nullptr;
  std::vector<unsigned> nCutsPerAtom(m->getNumAtoms(), 0);
  std::unique_ptr<ROMol> pieces(MolFragmenter::fragmentOnBonds(
      *m, bonds, add_dummies, dummyLabels, bondTypes, &nCutsPerAtom));
  REQUIRE(pieces);
  REQUIRE(nCutsPerAtom == std::vector<unsigned>{1, 1, 0, 0, 0, 0, 0, 0, 0});

  for (auto at : pieces->atoms()) {
    INFO("atom " + std::to_string(at->getIdx()));
    if (at->getAtomicNum() == 6) {
      CHECK(at->getNoImplicit() == (at->getIdx() == 1));
      CHECK(at->getTotalValence() == 4);
    }
  }
}

TEST_CASE(
    "GitHub #7327: SaltRemover may clear computed properties even if no atoms are removed",
    "[bug]") {
  auto m = "C=CC=O"_smiles;
  REQUIRE(m);
  REQUIRE(m->getRingInfo()->isSymmSssr());

  auto q = "[O,N]"_smarts;
  REQUIRE(q);

  bool onlyFrags = true;
  std::unique_ptr<ROMol> m2{deleteSubstructs(*m, *q, onlyFrags)};
  REQUIRE(m2);
  CHECK(m2->getNumAtoms() == m->getNumAtoms());  // No atoms removed
  CHECK(m2->getRingInfo()->isSymmSssr());
}

TEST_CASE(
    "Github #8288: molzip add linker bond functionality (fixes memory issue)",
    "[feature,bug]") {
  auto m = "[*:1][*:2].C[*:1].S[*:2]"_smiles;
  auto res = molzip(*m);
  CHECK(MolToSmiles(*res) == "CS");
}

TEST_CASE(
    "Github #8389: FragmentOnBonds does not preserve bond stereo when useLegacy=False") {
  auto useLegacy = GENERATE(true, false);
  CAPTURE(useLegacy);
  UseLegacyStereoPerceptionFixture fx(useLegacy);
  SECTION("as reported ") {
    auto m = "CC/C=C/N"_smiles;
    REQUIRE(m);
    std::unique_ptr<ROMol> res(
        MolFragmenter::fragmentOnBonds(*m, std::vector<unsigned int>{1}));
    REQUIRE(res);
    CHECK(res->getBondWithIdx(1)->getBondType() == Bond::BondType::DOUBLE);
    if (useLegacy) {
      CHECK(res->getBondWithIdx(1)->getStereo() == Bond::BondStereo::STEREOE);
    } else {
      CHECK(res->getBondWithIdx(1)->getStereo() ==
            Bond::BondStereo::STEREOTRANS);
    }

    CHECK(MolToSmiles(*res) == "[1*]/C=C/N.[2*]CC");
  }
}