rdkit/Code/MinimalLib/minilib.cpp

//
//
//  Copyright (C) 2019-2021 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 <string>
#include "minilib.h"
#include "common.h"

#include <RDGeneral/versions.h>
#include <GraphMol/RDKitBase.h>
#include <GraphMol/MolPickler.h>
#include <GraphMol/Chirality.h>
#include <GraphMol/SmilesParse/SmilesParse.h>
#include <GraphMol/SmilesParse/SmilesJSONParsers.h>
#include <GraphMol/SmilesParse/SmartsWrite.h>
#include <GraphMol/FileParsers/FileParsers.h>
#include <GraphMol/MolDraw2D/MolDraw2D.h>
#include <GraphMol/MolDraw2D/MolDraw2DSVG.h>
#include <GraphMol/MolDraw2D/MolDraw2DUtils.h>
#include <GraphMol/Substruct/SubstructMatch.h>
#ifdef RDK_BUILD_MINIMAL_LIB_SUBSTRUCTLIBRARY
#include <GraphMol/SubstructLibrary/SubstructLibrary.h>
#endif
#ifdef RDK_BUILD_MINIMAL_LIB_MCS
#include <GraphMol/FMCS/FMCS.h>
#endif
#ifdef RDK_BUILD_MINIMAL_LIB_MOLZIP
#include <GraphMol/ChemTransforms/MolFragmenterJSONParser.h>
#endif

#include <GraphMol/Descriptors/Property.h>
#include <GraphMol/Descriptors/MolDescriptors.h>
#include <GraphMol/MolInterchange/MolInterchange.h>
#include <GraphMol/CIPLabeler/CIPLabeler.h>
#include <GraphMol/Abbreviations/Abbreviations.h>
#include <GraphMol/MolTransforms/MolTransforms.h>
#include <Geometry/Transform3D.h>
#include <DataStructs/BitOps.h>
#include <DataStructs/ExplicitBitVect.h>
#ifdef RDK_BUILD_MINIMAL_LIB_RGROUPDECOMP
#include <GraphMol/RGroupDecomposition/RGroupDecompJSONParsers.h>
#endif

#ifdef RDK_BUILD_INCHI_SUPPORT
#include <INCHI-API/inchi.h>
#endif

#include <boost/json.hpp>

namespace bj = boost::json;

using namespace RDKit;

namespace {
#ifdef RDK_BUILD_MINIMAL_LIB_SUBSTRUCTLIBRARY
static const char *NO_SUPPORT_FOR_PATTERN_FPS =
    "This SubstructLibrary was built without support for pattern fps";
#endif

std::string mappingToJsonArray(const ROMol &mol) {
  std::vector<unsigned int> atomMapping;
  std::vector<unsigned int> bondMapping;
  mol.getPropIfPresent(Abbreviations::common_properties::origAtomMapping,
                       atomMapping);
  mol.getPropIfPresent(Abbreviations::common_properties::origBondMapping,
                       bondMapping);
  bj::object doc;
  bj::array bjAtoms;
  for (auto i : atomMapping) {
    bjAtoms.push_back(i);
  }
  doc["atoms"] = bjAtoms;

  bj::array bjBonds;
  for (auto i : bondMapping) {
    bjBonds.push_back(i);
  }
  doc["bonds"] = bjBonds;
  std::string res = bj::serialize(doc);
  return res;
}

void remove_hs_common(RWMol &mol, const std::string &details_json) {
  if (details_json.empty()) {
    MolOps::removeAllHs(mol);
  } else {
    MolOps::RemoveHsParameters ps;
    bool sanitize = true;
    MinimalLib::updateRemoveHsParametersFromJSON(ps, sanitize,
                                                 details_json.c_str());
    MolOps::removeHs(mol, ps, sanitize);
  }
}
}  // end of anonymous namespace

std::string JSMolBase::get_smiles() const { return MolToSmiles(get()); }
std::string JSMolBase::get_smiles(const std::string &details) const {
  SmilesWriteParams params;
  updateSmilesWriteParamsFromJSON(params, details);
  return MolToSmiles(get(), params);
}
std::string JSMolBase::get_cxsmiles() const { return MolToCXSmiles(get()); }
std::string JSMolBase::get_cxsmiles(const std::string &details) const {
  SmilesWriteParams params;
  updateSmilesWriteParamsFromJSON(params, details);
  std::uint32_t cxSmilesFields = SmilesWrite::CXSmilesFields::CX_ALL;
  unsigned int restoreBondDirs = RestoreBondDirOptionClear;
  updateCXSmilesFieldsFromJSON(cxSmilesFields, restoreBondDirs, details);
  return MolToCXSmiles(get(), params, cxSmilesFields,
                       static_cast<RestoreBondDirOption>(restoreBondDirs));
}
std::string JSMolBase::get_smarts() const { return MolToSmarts(get()); }
std::string JSMolBase::get_smarts(const std::string &details) const {
  SmilesWriteParams params;
  updateSmilesWriteParamsFromJSON(params, details);
  return MolToSmarts(get(), params.doIsomericSmiles, params.rootedAtAtom);
}
std::string JSMolBase::get_cxsmarts() const { return MolToCXSmarts(get()); }
std::string JSMolBase::get_cxsmarts(const std::string &details) const {
  SmilesWriteParams params;
  updateSmilesWriteParamsFromJSON(params, details);
  return MolToCXSmarts(get(), params.doIsomericSmiles);
}
std::string JSMolBase::get_svg(int w, int h) const {
  return MinimalLib::mol_to_svg(get(), w, h);
}
std::string JSMolBase::get_svg_with_highlights(
    const std::string &details) const {
  int w = d_defaultWidth;
  int h = d_defaultHeight;
  return MinimalLib::mol_to_svg(get(), w, h, details);
}

#ifdef RDK_BUILD_INCHI_SUPPORT
std::string JSMolBase::get_inchi(const std::string &options) const {
  ExtraInchiReturnValues rv;
  return MolToInchi(get(), rv, !options.empty() ? options.c_str() : nullptr);
}
#endif
std::string JSMolBase::get_molblock(const std::string &details) const {
  return MinimalLib::molblock_helper(get(), details.c_str(),
                                     MinimalLib::MDLVersion::AUTO);
}
std::string JSMolBase::get_v3Kmolblock(const std::string &details) const {
  return MinimalLib::molblock_helper(get(), details.c_str(),
                                     MinimalLib::MDLVersion::V3000);
}
std::string JSMolBase::get_v2Kmolblock(const std::string &details) const {
  return MinimalLib::molblock_helper(get(), details.c_str(),
                                     MinimalLib::MDLVersion::V2000);
}
std::string JSMolBase::get_json() const {
  return MolInterchange::MolToJSONData(get());
}

std::string JSMolBase::get_pickle(const std::string &details) const {
  unsigned int propFlags = PicklerOps::AllProps ^ PicklerOps::ComputedProps;
  MinimalLib::updatePropertyPickleOptionsFromJSON(propFlags, details.c_str());
  std::string pickle;
  MolPickler::pickleMol(get(), pickle, propFlags);
  return pickle;
}

std::string JSMolBase::get_substruct_match(const JSMolBase &q) const {
  std::string res = "{}";

  MatchVectType match;
  if (SubstructMatch(get(), q.get(), match)) {
    bj::object doc;
    MinimalLib::get_sss_json(get(), q.get(), match, doc);
    res = bj::serialize(doc);
  }

  return res;
}

std::string JSMolBase::get_substruct_matches(const JSMolBase &q) const {
  std::string res = "{}";

  auto matches = SubstructMatch(get(), q.get());
  if (!matches.empty()) {
    bj::array doc;

    for (const auto &match : matches) {
      bj::object bjMatch;
      MinimalLib::get_sss_json(get(), q.get(), match, bjMatch);
      doc.push_back(bjMatch);
    }

    res = bj::serialize(doc);
  }

  return res;
}

std::string JSMolBase::get_descriptors() const {
  return MinimalLib::get_descriptors(get());
}

std::string JSMolBase::get_morgan_fp(const std::string &details) const {
  auto fp = MinimalLib::morgan_fp_as_bitvect(get(), details.c_str());
  std::string res = BitVectToText(*fp);
  return res;
}

std::string JSMolBase::get_morgan_fp_as_binary_text(
    const std::string &details) const {
  auto fp = MinimalLib::morgan_fp_as_bitvect(get(), details.c_str());
  std::string res = BitVectToBinaryText(*fp);
  return res;
}

std::string JSMolBase::get_pattern_fp(const std::string &details) const {
  auto fp = MinimalLib::pattern_fp_as_bitvect(get(), details.c_str());
  std::string res = BitVectToText(*fp);
  return res;
}

std::string JSMolBase::get_pattern_fp_as_binary_text(
    const std::string &details) const {
  auto fp = MinimalLib::pattern_fp_as_bitvect(get(), details.c_str());
  std::string res = BitVectToBinaryText(*fp);
  return res;
}

std::string JSMolBase::get_topological_torsion_fp(
    const std::string &details) const {
  auto fp =
      MinimalLib::topological_torsion_fp_as_bitvect(get(), details.c_str());
  std::string res = BitVectToText(*fp);
  return res;
}

std::string JSMolBase::get_topological_torsion_fp_as_binary_text(
    const std::string &details) const {
  auto fp =
      MinimalLib::topological_torsion_fp_as_bitvect(get(), details.c_str());
  std::string res = BitVectToBinaryText(*fp);
  return res;
}

std::string JSMolBase::get_rdkit_fp(const std::string &details) const {
  auto fp = MinimalLib::rdkit_fp_as_bitvect(get(), details.c_str());
  std::string res = BitVectToText(*fp);
  return res;
}

std::string JSMolBase::get_rdkit_fp_as_binary_text(
    const std::string &details) const {
  auto fp = MinimalLib::rdkit_fp_as_bitvect(get(), details.c_str());
  std::string res = BitVectToBinaryText(*fp);
  return res;
}

std::string JSMolBase::get_atom_pair_fp(const std::string &details) const {
  auto fp = MinimalLib::atom_pair_fp_as_bitvect(get(), details.c_str());
  std::string res = BitVectToText(*fp);
  return res;
}

std::string JSMolBase::get_atom_pair_fp_as_binary_text(
    const std::string &details) const {
  auto fp = MinimalLib::atom_pair_fp_as_bitvect(get(), details.c_str());
  std::string res = BitVectToBinaryText(*fp);
  return res;
}

std::string JSMolBase::get_maccs_fp() const {
  auto fp = MinimalLib::maccs_fp_as_bitvect(get());
  std::string res = BitVectToText(*fp);
  return res;
}

std::string JSMolBase::get_maccs_fp_as_binary_text() const {
  auto fp = MinimalLib::maccs_fp_as_bitvect(get());
  std::string res = BitVectToBinaryText(*fp);
  return res;
}

#ifdef RDK_BUILD_AVALON_SUPPORT
std::string get_avalon_fp(const std::string &details) const {
  auto fp = MinimalLib::avalon_fp_as_bitvect(get(), details.c_str());
  std::string res = BitVectToText(*fp);
  return res;
}

std::string get_avalon_fp_as_binary_text(const std::string &details) const {
  auto fp = MinimalLib::avalon_fp_as_bitvect(get(), details.c_str());
  std::string res = BitVectToBinaryText(*fp);
  return res;
}
#endif

std::string JSMolBase::get_stereo_tags() {
  bj::object doc;

  bool cleanIt = true;
  bool force = true;
  bool flagPossibleStereocenters = true;
  MolOps::assignStereochemistry(get(), cleanIt, force,
                                flagPossibleStereocenters);
  CIPLabeler::assignCIPLabels(get());

  bj::array bjAtoms;
  for (const auto atom : get().atoms()) {
    std::string cip;
    if (!atom->getPropIfPresent(common_properties::_CIPCode, cip)) {
      if (atom->hasProp(common_properties::_ChiralityPossible)) {
        cip = "?";
      }
    }
    if (!cip.empty()) {
      cip = "(" + cip + ")";
      bj::array entry;
      entry.push_back(atom->getIdx());
      entry.push_back(cip.c_str());
      bjAtoms.push_back(std::move(entry));
    }
  }
  doc["CIP_atoms"] = bjAtoms;

  bj::array bjBonds;
  for (const auto bond : get().bonds()) {
    std::string cip;
    if (bond->getPropIfPresent(common_properties::_CIPCode, cip)) {
      cip = "(" + cip + ")";
      bj::array entry;
      entry.push_back(bond->getBeginAtomIdx());
      entry.push_back(bond->getEndAtomIdx());
      entry.push_back(cip.c_str());
      bjBonds.push_back(std::move(entry));
    }
  }

  doc["CIP_bonds"] = bjBonds;

  return bj::serialize(doc);
}

void JSMolBase::convert_to_aromatic_form() {
  get().updatePropertyCache();
  MolOps::setAromaticity(get());
}

std::string JSMolBase::get_aromatic_form() const {
  RWMol molCopy(get());
  molCopy.updatePropertyCache();
  MolOps::setAromaticity(molCopy);

  bool includeStereo = true;
  int confId = -1;
  bool kekulize = false;
  return MolToMolBlock(molCopy, includeStereo, confId, kekulize);
}

void JSMolBase::convert_to_kekule_form() { MolOps::Kekulize(get()); }

std::string JSMolBase::get_kekule_form() const {
  RWMol molCopy(get());
  MolOps::Kekulize(molCopy);

  bool includeStereo = true;
  int confId = -1;
  bool kekulize = true;
  return MolToMolBlock(molCopy, includeStereo, confId, kekulize);
}

bool JSMolBase::set_new_coords(bool useCoordGen) {
#ifdef RDK_BUILD_COORDGEN_SUPPORT
  bool oprefer = RDDepict::preferCoordGen;
  RDDepict::preferCoordGen = useCoordGen;
#endif
  RDDepict::compute2DCoords(get());
#ifdef RDK_BUILD_COORDGEN_SUPPORT
  RDDepict::preferCoordGen = oprefer;
#endif

  return true;
}

std::string JSMolBase::get_new_coords(bool useCoordGen) const {
  RWMol molCopy(get());

#ifdef RDK_BUILD_COORDGEN_SUPPORT
  bool oprefer = RDDepict::preferCoordGen;
  RDDepict::preferCoordGen = useCoordGen;
#endif
  RDDepict::compute2DCoords(molCopy);
#ifdef RDK_BUILD_COORDGEN_SUPPORT
  RDDepict::preferCoordGen = oprefer;
#endif

  return MolToMolBlock(molCopy);
}

bool JSMolBase::has_prop(const std::string &key) const {
  return get().hasProp(key);
}

std::vector<std::string> JSMolBase::get_prop_list(bool includePrivate,
                                                  bool includeComputed) const {
  return get().getPropList(includePrivate, includeComputed);
}

bool JSMolBase::set_prop(const std::string &key, const std::string &val,
                         bool computed) {
  get().setProp(key, val, computed);
  return true;
}

std::string JSMolBase::get_prop(const std::string &key) const {
  if (!get().hasProp(key)) {
    return "";
  }
  std::string val;
  get().getProp(key, val);
  return val;
}

bool JSMolBase::clear_prop(const std::string &key) {
  bool res = get().hasProp(key);
  if (res) {
    get().clearProp(key);
  }
  return res;
}

std::string JSMolBase::remove_hs(const std::string &details_json) const {
  RWMol molCopy(get());
  remove_hs_common(molCopy, details_json);

  bool includeStereo = true;
  int confId = -1;
  bool kekulize = true;
  return MolToMolBlock(molCopy, includeStereo, confId, kekulize);
}

bool JSMolBase::remove_hs_in_place(const std::string &details_json) {
  remove_hs_common(get(), details_json);
  MolOps::assignStereochemistry(get(), true, true);
  return true;
}

std::string JSMolBase::add_hs() const {
  RWMol molCopy(get());
  MolOps::addHs(molCopy);

  bool includeStereo = true;
  int confId = -1;
  bool kekulize = true;
  return MolToMolBlock(molCopy, includeStereo, confId, kekulize);
}

bool JSMolBase::add_hs_in_place() {
  bool addCoords = (get().getNumConformers() > 0);
  MolOps::addHs(get(), false, addCoords);
  MolOps::assignStereochemistry(get(), true, true);
  return true;
}

std::string JSMolBase::condense_abbreviations(double maxCoverage,
                                              bool useLinkers) {
  if (!useLinkers) {
    Abbreviations::condenseMolAbbreviations(
        get(), Abbreviations::Utils::getDefaultAbbreviations(), maxCoverage);
  } else {
    Abbreviations::condenseMolAbbreviations(
        get(), Abbreviations::Utils::getDefaultLinkers(), maxCoverage);
  }
  return mappingToJsonArray(get());
}

std::string JSMolBase::condense_abbreviations_from_defs(
    const std::string &definitions, double maxCoverage, bool areLinkers) {
  static std::string lastDefs = "";
  static std::vector<Abbreviations::AbbreviationDefinition> abbrevs;
  if (definitions != lastDefs) {
    // yes, we are making the assumption that the "areLinkers" argument remains
    // the same if the definitions are the same
    bool removeExtraDummies = areLinkers;
    bool allowConnectionToDummies = areLinkers;
    lastDefs = definitions;
    try {
      abbrevs = Abbreviations::Utils::parseAbbreviations(
          definitions, removeExtraDummies, allowConnectionToDummies);
    } catch (...) {
      return "cannot parse abbreviations";
    }
  }
  Abbreviations::condenseMolAbbreviations(get(), abbrevs, maxCoverage);
  return mappingToJsonArray(get());
}

std::string JSMolBase::generate_aligned_coords(const JSMolBase &templateMol,
                                               const std::string &details) {
  if (!templateMol.get().getNumConformers()) {
    return "";
  }
  return MinimalLib::generate_aligned_coords(get(), templateMol.get(),
                                             details.c_str());
}

int JSMolBase::has_coords() const {
  if (!get().getNumConformers()) {
    return 0;
  }
  return (get().getConformer().is3D() ? 3 : 2);
}

const RDGeom::POINT3D_VECT &JSMolBase::get_coords() const {
  static const RDGeom::POINT3D_VECT empty;
  return (get().getNumConformers() ? get().getConformer().getPositions()
                                   : empty);
}

double JSMolBase::normalize_depiction(int canonicalize, double scaleFactor) {
  if (!get().getNumConformers()) {
    return -1.;
  }
  return RDDepict::normalizeDepiction(get(), -1, canonicalize, scaleFactor);
}

void JSMolBase::straighten_depiction(bool minimizeRotation) {
  if (!get().getNumConformers()) {
    return;
  }
  RDDepict::straightenDepiction(get(), -1, minimizeRotation);
}

bool JSMolBase::is_valid() const { return true; }

std::pair<JSMolList *, std::string> JSMolBase::get_frags(
    const std::string &details_json) const {
  std::vector<int> frags;
  std::vector<std::vector<int>> fragsMolAtomMapping;
  bool sanitizeFrags = true;
  bool copyConformers = true;
  MinimalLib::get_mol_frags_details(details_json, sanitizeFrags,
                                    copyConformers);
  auto molFrags = MolOps::getMolFrags(get(), sanitizeFrags, &frags,
                                      &fragsMolAtomMapping, copyConformers);
  return std::make_pair(
      new JSMolList(molFrags),
      MinimalLib::get_mol_frags_mappings(frags, fragsMolAtomMapping));
}

unsigned int JSMolBase::get_num_atoms(bool heavyOnly) const {
  return heavyOnly ? get().getNumHeavyAtoms() : get().getNumAtoms();
}

unsigned int JSMolBase::get_num_bonds() const { return get().getNumBonds(); }

#ifdef RDK_BUILD_MINIMAL_LIB_MMPA
namespace {
bool mmpaFragmentMol(const ROMol &mol, std::vector<RDKit::ROMOL_SPTR> &cores,
                     std::vector<RDKit::ROMOL_SPTR> &sidechains,
                     unsigned int minCuts, unsigned int maxCuts,
                     unsigned int maxCutBonds) {
  std::vector<std::pair<RDKit::ROMOL_SPTR, RDKit::ROMOL_SPTR>> mmpaFrags;
  if (!RDKit::MMPA::fragmentMol(mol, mmpaFrags, minCuts, maxCuts,
                                maxCutBonds)) {
    return false;
  }
  auto numEntries = mmpaFrags.size();
  cores.clear();
  cores.reserve(numEntries);
  sidechains.clear();
  sidechains.reserve(numEntries);
  for (const auto &mmpaFrag : mmpaFrags) {
    cores.push_back(mmpaFrag.first);
    sidechains.push_back(mmpaFrag.second);
  }
  return true;
}
}  // end of anonymous namespace

std::pair<JSMolList *, JSMolList *> JSMolBase::get_mmpa_frags(
    unsigned int minCuts, unsigned int maxCuts,
    unsigned int maxCutBonds) const {
  std::vector<RDKit::ROMOL_SPTR> cores;
  std::vector<RDKit::ROMOL_SPTR> sidechains;
  if (!mmpaFragmentMol(get(), cores, sidechains, minCuts, maxCuts,
                       maxCutBonds)) {
    return std::make_pair(nullptr, nullptr);
  }
  return std::make_pair(new JSMolList(std::move(cores)),
                        new JSMolList(std::move(sidechains)));
}
#endif

std::string JSMolBase::add_to_png_blob(const std::string &pngString,
                                       const std::string &details) const {
  PNGMetadataParams params;
  std::string res;
  try {
    MinimalLib::updatePNGMetadataParamsFromJSON(params, details.c_str());
    res = addMolToPNGString(get(), pngString, params);
  } catch (...) {
  }
  return res;
}

std::string JSMolBase::combine_with(const JSMolBase &other,
                                    const std::string &details) {
  std::unique_ptr<ROMol> combinedMol;
  auto res = MinimalLib::combine_mols_internal(get(), other.get(), combinedMol,
                                               details.c_str());
  if (res.empty() && combinedMol) {
    reset(static_cast<RWMol *>(combinedMol.release()));
  }
  return "";
}

#ifdef RDK_BUILD_MINIMAL_LIB_RXN
std::string JSReaction::get_svg(int w, int h) const {
  assert(d_rxn);
  return MinimalLib::rxn_to_svg(*d_rxn, w, h);
}
std::string JSReaction::get_svg_with_highlights(
    const std::string &details) const {
  assert(d_rxn);

  int w = d_defaultWidth;
  int h = d_defaultHeight;
  return MinimalLib::rxn_to_svg(*d_rxn, w, h, details);
}
bool JSReaction::is_valid() const { return true; }

std::vector<JSMolList *> JSReaction::run_reactants(
    const JSMolList &reactants, unsigned int maxProducts) const {
  d_rxn->initReactantMatchers();
  RDKit::MOL_SPTR_VECT reactant_vec;

  for (const auto &reactant : reactants.mols()) {
    if (!reactant) {
      throw ValueErrorException("Reactant must not be null");
    }
    reactant_vec.push_back(reactant);
  }

  std::vector<RDKit::MOL_SPTR_VECT> prods;
  prods = d_rxn->runReactants(reactant_vec, maxProducts);
  std::vector<JSMolList *> newResults;
  for (auto &mol_array : prods) {
    newResults.push_back(new JSMolList(mol_array));
  }
  return newResults;
}
#endif

JSMolBase *JSMolList::next() {
  JSMolBase *res = nullptr;
  if (d_idx < d_mols.size()) {
    res = at(d_idx++);
  }
  return res;
}

JSMolBase *JSMolList::at(size_t idx) const {
  JSMolBase *res = nullptr;
  if (idx < d_mols.size()) {
    const auto &molSptr = d_mols.at(idx);
    if (molSptr) {
      res = new JSMolShared(molSptr);
    }
  }
  return res;
}

JSMolBase *JSMolList::pop(size_t idx) {
  JSMolBase *res = nullptr;
  if (idx < d_mols.size()) {
    res = at(idx);
    d_mols.erase(d_mols.begin() + idx);
    if (d_idx > idx) {
      --d_idx;
    }
  }
  return res;
}

size_t JSMolList::append(const JSMolBase &mol) {
  d_mols.emplace_back(new ROMol(mol.get()));
  return d_mols.size();
}

size_t JSMolList::insert(size_t idx, const JSMolBase &mol) {
  idx = std::min(idx, d_mols.size());
  d_mols.emplace(d_mols.begin() + idx, new ROMol(mol.get()));
  return d_mols.size();
}

#ifdef RDK_BUILD_MINIMAL_LIB_SUBSTRUCTLIBRARY
JSSubstructLibrary::JSSubstructLibrary(unsigned int num_bits)
    : d_fpHolder(nullptr) {
  boost::shared_ptr<CachedTrustedSmilesMolHolder> molHolderSptr(
      new CachedTrustedSmilesMolHolder());
  boost::shared_ptr<PatternHolder> fpHolderSptr;
  d_molHolder = molHolderSptr.get();
  if (num_bits) {
    fpHolderSptr.reset(new PatternHolder(num_bits));
    d_fpHolder = fpHolderSptr.get();
    d_sslib.reset(new SubstructLibrary(molHolderSptr, fpHolderSptr));
  } else {
    d_sslib.reset(new SubstructLibrary(molHolderSptr));
  }
}

int JSSubstructLibrary::add_trusted_smiles(const std::string &smi) {
  SmilesParserParams ps;
  ps.sanitize = false;
  ps.removeHs = false;
  std::unique_ptr<RWMol> mol(SmilesToMol(smi, ps));
  if (!mol) {
    return -1;
  }
  mol->updatePropertyCache();
  MolOps::fastFindRings(*mol);
  int smiIdx;
  if (d_fpHolder) {
    auto fp = d_fpHolder->makeFingerprint(*mol);
    if (!fp) {
      return -1;
    }
    int fpIdx = d_fpHolder->addFingerprint(fp);
    smiIdx = d_molHolder->addSmiles(smi);
    CHECK_INVARIANT(fpIdx == smiIdx, "");
  } else {
    smiIdx = d_molHolder->addSmiles(smi);
  }
  return smiIdx;
}

int JSSubstructLibrary::add_trusted_smiles_and_pattern_fp(
    const std::string &smi, const std::string &patternFp) {
  if (!d_fpHolder) {
    throw ValueErrorException(NO_SUPPORT_FOR_PATTERN_FPS);
  }
  auto bitVect = new ExplicitBitVect(patternFp);
  if (!bitVect) {
    return -1;
  }
  int fpIdx = d_fpHolder->addFingerprint(bitVect);
  int smiIdx = d_molHolder->addSmiles(smi);
  CHECK_INVARIANT(fpIdx == smiIdx, "");
  return smiIdx;
}

std::string JSSubstructLibrary::get_trusted_smiles(unsigned int i) const {
  return d_molHolder->getMols().at(i);
}

std::string JSSubstructLibrary::get_pattern_fp(unsigned int i) const {
  if (!d_fpHolder) {
    throw ValueErrorException(NO_SUPPORT_FOR_PATTERN_FPS);
  }
  return d_fpHolder->getFingerprints().at(i)->toString();
}

inline int JSSubstructLibrary::add_mol_helper(const ROMol &mol) {
  std::string smi = MolToSmiles(mol);
  return add_trusted_smiles(smi);
}

int JSSubstructLibrary::add_mol(const JSMolBase &m) {
  return add_mol_helper(m.get());
}

int JSSubstructLibrary::add_smiles(const std::string &smi) {
  std::unique_ptr<RWMol> mol(SmilesToMol(smi));
  if (!mol) {
    return -1;
  }
  return add_mol_helper(*mol);
}

JSMolBase *JSSubstructLibrary::get_mol(unsigned int i) {
  return new JSMolShared(d_sslib->getMol(i));
}

std::string JSSubstructLibrary::get_matches(const JSMolBase &q,
                                            bool useChirality, int numThreads,
                                            int maxResults) const {
  if (!d_sslib->size()) {
    return "[]";
  }
  auto indices = d_sslib->getMatches(q.get(), true, useChirality, false,
                                     numThreads, maxResults);
  bj::array doc;
  for (const auto &i : indices) {
    doc.push_back(i);
  }
  std::string res = bj::serialize(doc);
  return res;
}

unsigned int JSSubstructLibrary::count_matches(const JSMolBase &q,
                                               bool useChirality,
                                               int numThreads) const {
  return d_sslib->size() ? d_sslib->countMatches(q.get(), true, useChirality,
                                                 false, numThreads)
                         : 0;
}
#endif

#ifdef RDK_BUILD_INCHI_SUPPORT
std::string get_inchikey_for_inchi(const std::string &input) {
  return InchiToInchiKey(input);
}
#endif

JSMolBase *get_mol_copy(const JSMolBase &other) {
  return new JSMol(new RWMol(other.get()));
}

JSMolBase *get_mol(const std::string &input, const std::string &details_json) {
  auto mol = MinimalLib::mol_from_input(input, details_json);
  return mol ? new JSMol(mol) : nullptr;
}

JSMolBase *get_mol_from_pickle(const std::string &pkl) {
  RWMol *mol = nullptr;
  if (!pkl.empty()) {
    mol = new RWMol();
    try {
      MolPickler::molFromPickle(pkl, mol);
    } catch (...) {
      delete mol;
      mol = nullptr;
    }
  }
  return mol ? new JSMol(mol) : nullptr;
}

JSMolBase *get_qmol(const std::string &input) {
  auto mol = MinimalLib::qmol_from_input(input);
  return mol ? new JSMol(mol) : nullptr;
}

#ifdef RDK_BUILD_MINIMAL_LIB_RXN
JSReaction *get_rxn(const std::string &input, const std::string &details_json) {
  auto rxn = MinimalLib::rxn_from_input(input, details_json);
  return rxn ? new JSReaction(rxn) : nullptr;
}
#endif

std::string version() { return std::string(rdkitVersion); }

void prefer_coordgen(bool useCoordGen) {
#ifdef RDK_BUILD_COORDGEN_SUPPORT
  RDDepict::preferCoordGen = useCoordGen;
#endif
}

bool use_legacy_stereo_perception(bool value) {
  bool was = Chirality::getUseLegacyStereoPerception();
  Chirality::setUseLegacyStereoPerception(value);
  return was;
}

bool allow_non_tetrahedral_chirality(bool value) {
  bool was = Chirality::getAllowNontetrahedralChirality();
  Chirality::setAllowNontetrahedralChirality(value);
  return was;
}

#ifdef RDK_BUILD_MINIMAL_LIB_MCS
namespace {
MCSResult getMcsResult(const JSMolList &molList,
                       const std::string &details_json) {
  MCSParameters p;
  if (!details_json.empty()) {
    parseMCSParametersJSON(details_json.c_str(), &p);
  }
  return RDKit::findMCS(molList.mols(), &p);
}
}  // namespace

std::string get_mcs_as_json(const JSMolList &molList,
                            const std::string &details_json) {
  auto mcsResult = getMcsResult(molList, details_json);
  bj::object doc;
  bj::value bjSmarts;
  if (!mcsResult.DegenerateSmartsQueryMolDict.empty()) {
    bj::array smartsArray;
    for (const auto &pair : mcsResult.DegenerateSmartsQueryMolDict) {
      smartsArray.emplace_back(pair.first);
    }
    bjSmarts = smartsArray;
  } else {
    bjSmarts = mcsResult.SmartsString;
  }
  doc["smarts"] = bjSmarts;
  doc["canceled"] = mcsResult.Canceled;
  doc["numAtoms"] = mcsResult.NumAtoms;
  doc["numBonds"] = mcsResult.NumBonds;
  std::string res = bj::serialize(doc);
  return res;
}

std::string get_mcs_as_smarts(const JSMolList &molList,
                              const std::string &details_json) {
  auto res = getMcsResult(molList, details_json);
  return res.SmartsString;
}

JSMolBase *get_mcs_as_mol(const JSMolList &molList,
                          const std::string &details_json) {
  auto res = getMcsResult(molList, details_json);
  return new JSMolShared(res.QueryMol);
}
#endif

std::unique_ptr<MinimalLib::LoggerStateSingletons>
    MinimalLib::LoggerStateSingletons::d_instance;

JSLog::JSLog(MinimalLib::LogHandle *logHandle) : d_logHandle(logHandle) {
  assert(d_logHandle);
}

JSLog::~JSLog() { delete d_logHandle; }

std::string JSLog::get_buffer() const { return d_logHandle->getBuffer(); }

void JSLog::clear_buffer() const { d_logHandle->clearBuffer(); }

JSLog *set_log_tee(const std::string &log_name) {
  auto logHandle = MinimalLib::LogHandle::setLogTee(log_name.c_str());
  return logHandle ? new JSLog(logHandle) : nullptr;
}

JSLog *set_log_capture(const std::string &log_name) {
  auto logHandle = MinimalLib::LogHandle::setLogCapture(log_name.c_str());
  return logHandle ? new JSLog(logHandle) : nullptr;
}

bool enable_logging(const std::string &logName) {
  return MinimalLib::LogHandle::enableLogging(logName.c_str());
}

bool disable_logging(const std::string &logName) {
  return MinimalLib::LogHandle::disableLogging(logName.c_str());
}

void disable_logging() { RDKit::MinimalLib::LogHandle::disableLogging(); }

JSMolBase *get_mol_from_png_blob(const std::string &pngString,
                                 const std::string &details) {
  auto mols = MinimalLib::get_mols_from_png_blob_internal(pngString, true,
                                                          details.c_str());
  if (mols.empty()) {
    return nullptr;
  }
  return new JSMol(new RWMol(*mols.front()));
}

JSMolList *get_mols_from_png_blob(const std::string &pngString,
                                  const std::string &details) {
  auto mols = MinimalLib::get_mols_from_png_blob_internal(pngString, false,
                                                          details.c_str());
  if (mols.empty()) {
    return nullptr;
  }
  return new JSMolList(mols);
}

#ifdef RDK_BUILD_MINIMAL_LIB_RGROUPDECOMP
JSRGroupDecomposition::JSRGroupDecomposition(const JSMolBase &core,
                                             const std::string &details_json) {
  RGroupDecompositionParameters params;
  updateRGroupDecompositionParametersFromJSON(params, details_json);
  d_decomp.reset(new RGroupDecomposition(core.get(), params));
}

JSRGroupDecomposition::JSRGroupDecomposition(const JSMolList &cores,
                                             const std::string &details_json) {
  RGroupDecompositionParameters params;
  updateRGroupDecompositionParametersFromJSON(params, details_json);
  d_decomp.reset(new RGroupDecomposition(cores.mols(), params));
}

int JSRGroupDecomposition::add(const JSMolBase &mol) {
  return d_decomp->add(mol.get());
}

bool JSRGroupDecomposition::process() { return d_decomp->process(); }

std::map<std::string, std::unique_ptr<JSMolList>>
JSRGroupDecomposition::getRGroupsAsColumns() const {
  auto cols = d_decomp->getRGroupsAsColumns();
  std::map<std::string, std::unique_ptr<JSMolList>> res;
  std::transform(
      cols.begin(), cols.end(), std::inserter(res, res.begin()),
      [](const auto &keyValuePair) {
        return std::make_pair(
            std::move(keyValuePair.first),
            std::unique_ptr<JSMolList>(new JSMolList(keyValuePair.second)));
      });
  return res;
}

std::vector<std::map<std::string, std::unique_ptr<JSMolBase>>>
JSRGroupDecomposition::getRGroupsAsRows() const {
  auto rows = d_decomp->getRGroupsAsRows();
  std::vector<std::map<std::string, std::unique_ptr<JSMolBase>>> res;
  res.reserve(rows.size());
  std::transform(
      rows.begin(), rows.end(), std::back_inserter(res),
      [](const auto &originalMap) {
        std::map<std::string, std::unique_ptr<JSMolBase>> transformedMap;
        std::transform(originalMap.begin(), originalMap.end(),
                       std::inserter(transformedMap, transformedMap.begin()),
                       [](const auto &keyValuePair) {
                         CHECK_INVARIANT(keyValuePair.second,
                                         "ROMOL_SPTR must not be null");
                         return std::make_pair(
                             std::move(keyValuePair.first),
                             std::unique_ptr<JSMolBase>(
                                 new JSMolShared(keyValuePair.second)));
                       });
        return transformedMap;
      });
  return res;
}
#endif
#ifdef RDK_BUILD_MINIMAL_LIB_MOLZIP
JSMolBase *molzip(const JSMolBase &a, const JSMolBase &b,
                  const std::string &details_json) {
  MolzipParams params;
  parseMolzipParametersJSON(params, details_json.c_str());
  auto out = molzip(a.get(), b.get(), params);
  return new JSMol(new RDKit::RWMol(*out));
}
#endif