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rdkit/Code/GraphMol/Depictor/RDDepictor.cpp
Ricardo Rodriguez 92d5d2c657 Refactor to stop using iterator definitions in types.h (#9275) 
* clean up iterator defs in types.h

* do not use auto for inline constexpr

* restore undef max,min

* restore types.h declarations
2026-05-21 19:19:38 +02:00

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//
// Copyright (C) 2003-2022 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 "RDDepictor.h"
#include "EmbeddedFrag.h"
#include "Templates.h"
#ifdef RDK_BUILD_COORDGEN_SUPPORT
#include <CoordGen/CoordGen.h>
#endif
#include <RDGeneral/types.h>
#include <GraphMol/ROMol.h>
#include <GraphMol/Conformer.h>
#include <GraphMol/Chirality.h>
#include <cmath>
#include <GraphMol/MolOps.h>
#include <GraphMol/Rings.h>
#include <GraphMol/QueryAtom.h>
#include <Geometry/point.h>
#include <GraphMol/MolAlign/AlignMolecules.h>
#include <GraphMol/MolTransforms/MolTransforms.h>
#include <GraphMol/Substruct/SubstructUtils.h>
#include <GraphMol/Chirality.h>
#include "EmbeddedFrag.h"
#include "DepictUtils.h"
#include <boost/dynamic_bitset.hpp>
#include <algorithm>
namespace RDDepict {
bool preferCoordGen = false;
namespace DepictorLocal {
constexpr auto ISQRT2 = 0.707107;
constexpr auto SQRT3_2 = 0.866025;
std::vector<const RDKit::Atom *> getRankedAtomNeighbors(
const RDKit::ROMol &mol, const RDKit::Atom *atom,
const std::vector<int> &atomRanks) {
std::vector<const RDKit::Atom *> nbrs;
for (auto nbr : mol.atomNeighbors(atom)) {
nbrs.push_back(nbr);
}
std::sort(nbrs.begin(), nbrs.end(),
[&atomRanks](const auto e1, const auto e2) {
return atomRanks[e1->getIdx()] < atomRanks[e2->getIdx()];
});
return nbrs;
}
void embedSquarePlanar(const RDKit::ROMol &mol, const RDKit::Atom *atom,
std::list<EmbeddedFrag> &efrags,
const std::vector<int> &atomRanks) {
static const RDGeom::Point2D idealPoints[] = {
RDGeom::Point2D(ISQRT2 * BOND_LEN, ISQRT2 * BOND_LEN),
RDGeom::Point2D(ISQRT2 * BOND_LEN, -ISQRT2 * BOND_LEN),
RDGeom::Point2D(-ISQRT2 * BOND_LEN, -ISQRT2 * BOND_LEN),
RDGeom::Point2D(-ISQRT2 * BOND_LEN, ISQRT2 * BOND_LEN),
};
PRECONDITION(atom, "bad atom");
if (atom->getChiralTag() != RDKit::Atom::ChiralType::CHI_SQUAREPLANAR) {
return;
}
auto nbrs = getRankedAtomNeighbors(mol, atom, atomRanks);
RDGeom::INT_POINT2D_MAP coordMap;
coordMap[atom->getIdx()] = RDGeom::Point2D(0., 0.);
coordMap[nbrs[0]->getIdx()] = idealPoints[0];
bool q2Full = false;
for (const auto nbr : nbrs) {
if (nbr == nbrs.front()) {
continue;
}
auto angle =
RDKit::Chirality::getIdealAngleBetweenLigands(atom, nbrs.front(), nbr);
if (fabs(angle - 180) < 0.1) {
coordMap[nbr->getIdx()] = idealPoints[2];
} else {
if (!q2Full) {
coordMap[nbr->getIdx()] = idealPoints[1];
q2Full = true;
} else {
coordMap[nbr->getIdx()] = idealPoints[3];
}
}
}
efrags.emplace_back(&mol, coordMap);
}
void embedTBP(const RDKit::ROMol &mol, const RDKit::Atom *atom,
std::list<EmbeddedFrag> &efrags,
const std::vector<int> &atomRanks) {
static const RDGeom::Point2D idealPoints[] = {
RDGeom::Point2D(0, BOND_LEN), // axial
RDGeom::Point2D(0, -BOND_LEN), // axial
RDGeom::Point2D(-SQRT3_2 * BOND_LEN, BOND_LEN / 2), // equatorial
RDGeom::Point2D(-SQRT3_2 * BOND_LEN,
-BOND_LEN / 2), // equatorial
RDGeom::Point2D(BOND_LEN, 0), // equatorial
};
PRECONDITION(atom, "bad atom");
if (atom->getChiralTag() !=
RDKit::Atom::ChiralType::CHI_TRIGONALBIPYRAMIDAL) {
return;
}
auto nbrs = getRankedAtomNeighbors(mol, atom, atomRanks);
RDGeom::INT_POINT2D_MAP coordMap;
coordMap[atom->getIdx()] = RDGeom::Point2D(0., 0.);
const RDKit::Atom *axial1 =
RDKit::Chirality::getTrigonalBipyramidalAxialAtom(atom);
const RDKit::Atom *axial2 =
RDKit::Chirality::getTrigonalBipyramidalAxialAtom(atom, -1);
if (axial1) {
coordMap[axial1->getIdx()] = idealPoints[0];
}
if (axial2) {
coordMap[axial2->getIdx()] = idealPoints[1];
}
unsigned whichEq = 2;
for (const auto nbr : nbrs) {
if (nbr != axial1 && nbr != axial2) {
coordMap[nbr->getIdx()] = idealPoints[whichEq++];
}
}
efrags.emplace_back(&mol, coordMap);
}
void embedOctahedral(const RDKit::ROMol &mol, const RDKit::Atom *atom,
std::list<EmbeddedFrag> &efrags,
const std::vector<int> &atomRanks) {
static const RDGeom::Point2D idealPoints[] = {
RDGeom::Point2D(0, BOND_LEN), // axial
RDGeom::Point2D(0, -BOND_LEN), // axial
RDGeom::Point2D(SQRT3_2 * BOND_LEN, BOND_LEN / 2), // equatorial
RDGeom::Point2D(SQRT3_2 * BOND_LEN, -BOND_LEN / 2), // equatorial
RDGeom::Point2D(-SQRT3_2 * BOND_LEN, -BOND_LEN / 2), // equatorial
RDGeom::Point2D(-SQRT3_2 * BOND_LEN, BOND_LEN / 2), // equatorial
};
PRECONDITION(atom, "bad atom");
if (atom->getChiralTag() != RDKit::Atom::ChiralType::CHI_OCTAHEDRAL) {
return;
}
auto nbrs = getRankedAtomNeighbors(mol, atom, atomRanks);
RDGeom::INT_POINT2D_MAP coordMap;
coordMap[atom->getIdx()] = RDGeom::Point2D(0., 0.);
const RDKit::Atom *axial1 = nullptr;
const RDKit::Atom *axial2 = nullptr;
for (auto i = 0u; i < nbrs.size(); ++i) {
bool all90 = true;
for (auto j = i + 1; j < nbrs.size(); ++j) {
if (fabs(RDKit::Chirality::getIdealAngleBetweenLigands(atom, nbrs[i],
nbrs[j]) -
180) < 0.1) {
axial1 = nbrs[i];
axial2 = nbrs[j];
all90 = false;
break;
} else if (fabs(RDKit::Chirality::getIdealAngleBetweenLigands(
atom, nbrs[i], nbrs[j]) -
90) > 0.1) {
all90 = false;
}
}
if (all90) {
axial1 = nbrs[i];
}
if (axial1) {
break;
}
}
if (axial1) {
coordMap[axial1->getIdx()] = idealPoints[0];
}
if (axial2) {
coordMap[axial2->getIdx()] = idealPoints[1];
}
const RDKit::Atom *refEqAtom1 = nullptr;
const RDKit::Atom *refEqAtom2 = nullptr;
for (const auto nbr : nbrs) {
if (nbr != axial1 && nbr != axial2) {
if (!refEqAtom1) {
refEqAtom1 = nbr;
coordMap[nbr->getIdx()] = idealPoints[2];
refEqAtom2 = RDKit::Chirality::getChiralAcrossAtom(atom, nbr);
if (refEqAtom2) {
coordMap[refEqAtom2->getIdx()] = idealPoints[4];
}
} else {
if (nbr == refEqAtom2 || nbr == refEqAtom1) {
continue;
}
coordMap[nbr->getIdx()] = idealPoints[3];
const auto acrossAtom2 =
RDKit::Chirality::getChiralAcrossAtom(atom, nbr);
if (acrossAtom2) {
coordMap[acrossAtom2->getIdx()] = idealPoints[5];
}
break;
}
}
}
efrags.emplace_back(&mol, coordMap);
}
void embedNontetrahedralStereo(const RDKit::ROMol &mol,
std::list<EmbeddedFrag> &efrags,
const std::vector<int> &atomRanks) {
boost::dynamic_bitset<> consider(mol.getNumAtoms());
for (const auto atm : mol.atoms()) {
if (RDKit::Chirality::hasNonTetrahedralStereo(atm)) {
consider[atm->getIdx()] = 1;
}
}
if (consider.empty()) {
return;
}
for (const auto atm : mol.atoms()) {
if (!consider[atm->getIdx()]) {
continue;
}
switch (atm->getChiralTag()) {
case RDKit::Atom::ChiralType::CHI_SQUAREPLANAR:
embedSquarePlanar(mol, atm, efrags, atomRanks);
break;
case RDKit::Atom::ChiralType::CHI_TRIGONALBIPYRAMIDAL:
embedTBP(mol, atm, efrags, atomRanks);
break;
case RDKit::Atom::ChiralType::CHI_OCTAHEDRAL:
embedOctahedral(mol, atm, efrags, atomRanks);
break;
default:
break;
}
}
}
// arings: indices of atoms in rings
void embedFusedSystems(const RDKit::ROMol &mol,
const RDKit::VECT_INT_VECT &arings,
std::list<EmbeddedFrag> &efrags,
const RDGeom::INT_POINT2D_MAP *coordMap,
bool useRingTemplates) {
RDKit::INT_INT_VECT_MAP neighMap;
RingUtils::makeRingNeighborMap(arings, neighMap);
auto cnrs = arings.size();
boost::dynamic_bitset<> fusDone(cnrs);
auto curr = 0u;
while (curr < cnrs) {
// embed all ring and fused ring systems
RDKit::INT_VECT fused;
RingUtils::pickFusedRings(curr, neighMap, fused, fusDone);
RDKit::VECT_INT_VECT frings;
frings.reserve(fused.size());
for (auto rid : fused) {
frings.push_back(arings.at(rid));
}
// don't allow ring system templates if >1 atom in this ring system
// has a user-defined coordinate from coordMap
bool allowRingTemplates = useRingTemplates;
if (useRingTemplates && coordMap) {
boost::dynamic_bitset<> coordMapAtoms(mol.getNumAtoms());
for (const auto &ring : frings) {
for (const auto &aid : ring) {
if (coordMap->find(aid) != coordMap->end()) {
coordMapAtoms.set(aid);
}
}
}
allowRingTemplates = (coordMapAtoms.count() < 2);
}
EmbeddedFrag efrag(&mol, frings, allowRingTemplates);
efrag.setupNewNeighs();
efrags.push_back(efrag);
size_t rix;
for (rix = 0; rix < cnrs; ++rix) {
if (!fusDone[rix]) {
curr = rix;
break;
}
}
if (rix == cnrs) {
break;
}
}
}
void embedCisTransSystems(const RDKit::ROMol &mol,
std::list<EmbeddedFrag> &efrags) {
for (auto bond : mol.bonds()) {
// check if this bond is in a cis/trans double bond
// and it is not a ring bond
if ((bond->getBondType() == RDKit::Bond::DOUBLE) // this is a double bond
&& (bond->getStereo() >
RDKit::Bond::STEREOANY) // and has stereo chemistry specified
&& (!bond->getOwningMol().getRingInfo()->numBondRings(
bond->getIdx()))) { // not in a ring
if (bond->getStereoAtoms().size() != 2) {
BOOST_LOG(rdWarningLog)
<< "WARNING: bond found with stereo spec but no stereo atoms"
<< std::endl;
continue;
}
EmbeddedFrag efrag(bond);
efrag.setupNewNeighs();
efrags.push_back(efrag);
}
}
}
RDKit::INT_LIST getNonEmbeddedAtoms(const RDKit::ROMol &mol,
const std::list<EmbeddedFrag> &efrags) {
RDKit::INT_LIST res;
boost::dynamic_bitset<> done(mol.getNumAtoms());
for (const auto &efrag : efrags) {
const auto &oatoms = efrag.GetEmbeddedAtoms();
for (const auto &oatom : oatoms) {
done[oatom.first] = 1;
}
}
for (auto aid = 0u; aid < mol.getNumAtoms(); ++aid) {
if (!done[aid]) {
res.push_back(aid);
}
}
return res;
}
// find the largest fragments that is not done yet (
// i.e. merged with the master fragments)
// if do not find anything we return efrags.end()
std::list<EmbeddedFrag>::iterator _findLargestFrag(
std::list<EmbeddedFrag> &efrags) {
std::list<EmbeddedFrag>::iterator mfri;
int msiz = 0;
for (auto efri = efrags.begin(); efri != efrags.end(); ++efri) {
if ((!efri->isDone()) && (efri->Size() > msiz)) {
msiz = efri->Size();
mfri = efri;
}
}
if (msiz == 0) {
mfri = efrags.end();
}
return mfri;
}
void _shiftCoords(std::list<EmbeddedFrag> &efrags) {
// shift the coordinates if there are multiple fragments
// so that the fragments do not overlap each other
if (efrags.empty()) {
return;
}
for (auto &efrag : efrags) {
efrag.computeBox();
}
auto eri = efrags.begin();
auto xmax = eri->getBoxPx();
auto xmin = eri->getBoxNx();
auto ymax = eri->getBoxPy();
auto ymin = eri->getBoxNy();
++eri;
while (eri != efrags.end()) {
bool xshift = true;
if (xmax + xmin > ymax + ymin) {
xshift = false;
}
auto xn = eri->getBoxNx();
auto xp = eri->getBoxPx();
auto yn = eri->getBoxNy();
auto yp = eri->getBoxPy();
RDGeom::Point2D shift(0.0, 0.0);
if (xshift) {
shift.x = xmax + xn + 1.0;
shift.y = 0.0;
xmax += xp + xn + 1.0;
} else {
shift.x = 0.0;
shift.y = ymax + yn + 1.0;
ymax += yp + yn + 1.0;
}
eri->Translate(shift);
++eri;
}
}
// we do not use std::copysign as we need a tolerance
double copySign(double to, double from, double tol) {
return (from < -tol ? -fabs(to) : fabs(to));
}
struct ThetaBin {
double d_thetaAvg = 0.0;
std::vector<double> thetaValues;
};
} // namespace DepictorLocal
void computeInitialCoords(RDKit::ROMol &mol,
const RDGeom::INT_POINT2D_MAP *coordMap,
std::list<EmbeddedFrag> &efrags,
bool useRingTemplates) {
std::vector<int> atomRanks;
atomRanks.resize(mol.getNumAtoms());
for (auto i = 0u; i < mol.getNumAtoms(); ++i) {
atomRanks[i] = getAtomDepictRank(mol.getAtomWithIdx(i));
}
RDKit::VECT_INT_VECT arings;
// first find all the rings
bool includeDativeBonds = true;
RDKit::MolOps::symmetrizeSSSR(mol, arings, includeDativeBonds);
// do stereochemistry
RDKit::MolOps::assignStereochemistry(mol, false);
efrags.clear();
// user-specified coordinates exist
bool preSpec = false;
// first embed any atoms for which the coordinates have been specified.
if ((coordMap) && (coordMap->size() > 1)) {
EmbeddedFrag efrag(&mol, *coordMap);
// add this to the list of embedded fragments
efrags.push_back(efrag);
preSpec = true;
}
if (arings.size() > 0) {
// first deal with the fused rings
DepictorLocal::embedFusedSystems(mol, arings, efrags, coordMap,
useRingTemplates);
}
// do non-tetrahedral stereo
DepictorLocal::embedNontetrahedralStereo(mol, efrags, atomRanks);
// deal with any cis/trans systems
DepictorLocal::embedCisTransSystems(mol, efrags);
// now get the atoms that are not yet embedded in either a cis/trans system
// or a ring system (or simply the first atom)
auto nratms = DepictorLocal::getNonEmbeddedAtoms(mol, efrags);
std::list<EmbeddedFrag>::iterator mri;
if (preSpec) {
// if the user specified coordinates on some of the atoms use that as
// as the starting fragment and it should be at the beginning of the vector
mri = efrags.begin();
} else {
// otherwise - find the largest fragment that was embedded
mri = DepictorLocal::_findLargestFrag(efrags);
}
while ((mri != efrags.end()) || (nratms.size() > 0)) {
if (mri == efrags.end()) {
// we are out of embedded fragments, if there are any
// non embedded atoms use them to start a fragment
auto mrank = RDKit::MAX_INT;
auto mnri = nratms.end();
for (auto nri = nratms.begin(); nri != nratms.end(); ++nri) {
auto rank = atomRanks.at(*nri);
rank *= mol.getNumAtoms();
// use the atom index as well so that we at least
// get reproducible depictions in cases where things
// have identical ranks.
rank += *nri;
if (rank < mrank) {
mrank = rank;
mnri = nri;
}
}
EmbeddedFrag efrag((*mnri), &mol);
nratms.erase(mnri);
efrags.push_back(efrag);
mri = efrags.end();
--mri;
}
mri->markDone();
mri->expandEfrag(nratms, efrags);
mri = DepictorLocal::_findLargestFrag(efrags);
}
// at this point any remaining efrags should belong individual fragments in
// the molecule
}
unsigned int copyCoordinate(RDKit::ROMol &mol, std::list<EmbeddedFrag> &efrags,
bool clearConfs) {
// create a conformation to store the coordinates and add it to the molecule
auto *conf = new RDKit::Conformer(mol.getNumAtoms());
conf->set3D(false);
std::list<EmbeddedFrag>::iterator eri;
for (const auto &efrag : efrags) {
for (const auto &eai : efrag.GetEmbeddedAtoms()) {
const auto &cr = eai.second.loc;
RDGeom::Point3D fcr(cr.x, cr.y, 0.0);
conf->setAtomPos(eai.first, fcr);
}
}
unsigned int confId = 0;
if (clearConfs) {
// clear all the conformation on the molecules and assign conf ID 0 to this
// conformation
mol.clearConformers();
conf->setId(confId);
// conf ID has already been set in this case to 0 - not other
// confs on the molecule at this point
mol.addConformer(conf);
} else {
// let add conf assign a conformation ID for the conformation
confId = mol.addConformer(conf, true);
}
return confId;
}
void setRingSystemTemplates(const std::string template_path) {
// CoordinateTemplates is a singleton that holds all the templates, starting
// with the default templates if different templates are set using
// `RDDepictor::SetRingSystemTemplates`, the default templates are replaced by
// the new templates
CoordinateTemplates &coordinate_templates =
CoordinateTemplates::getRingSystemTemplates();
coordinate_templates.setRingSystemTemplates(template_path);
}
void addRingSystemTemplates(const std::string template_path) {
CoordinateTemplates &coordinate_templates =
CoordinateTemplates::getRingSystemTemplates();
coordinate_templates.addRingSystemTemplates(template_path);
}
void loadDefaultRingSystemTemplates() {
CoordinateTemplates &coordinate_templates =
CoordinateTemplates::getRingSystemTemplates();
coordinate_templates.loadDefaultTemplates();
}
unsigned int compute2DCoords(RDKit::ROMol &mol,
const RDGeom::INT_POINT2D_MAP *coordMap,
bool canonOrient, bool clearConfs,
unsigned int nFlipsPerSample,
unsigned int nSamples, int sampleSeed,
bool permuteDeg4Nodes, bool forceRDKit,
bool useRingTemplates) {
Compute2DCoordParameters params;
params.coordMap = coordMap;
params.canonOrient = canonOrient;
params.clearConfs = clearConfs;
params.nFlipsPerSample = nFlipsPerSample;
params.nSamples = nSamples;
params.sampleSeed = sampleSeed;
params.permuteDeg4Nodes = permuteDeg4Nodes;
params.forceRDKit = forceRDKit;
params.useRingTemplates = useRingTemplates;
return compute2DCoords(mol, params);
}
//
//
// 50,000 foot algorithm:
// 1) Find rings
// 2) Find fused systems
// 3) embed largest fused system
// 4) for each unfinished atom:
// 1) find neighbors
// 2) if neighbor is non-ring atom, embed it; otherwise merge the
// ring system
// 3) add all atoms just merged/embedded to unfinished atom list
//
//
unsigned int compute2DCoords(RDKit::ROMol &mol,
const Compute2DCoordParameters &params) {
if (mol.needsUpdatePropertyCache()) {
mol.updatePropertyCache(false);
}
#ifdef RDK_BUILD_COORDGEN_SUPPORT
// default to use CoordGen if we have it installed
if (!params.forceRDKit && preferCoordGen) {
RDKit::CoordGen::CoordGenParams coordgen_params;
if (params.coordMap) {
coordgen_params.coordMap = *params.coordMap;
}
auto cid = RDKit::CoordGen::addCoords(mol, &coordgen_params);
return cid;
};
#endif
RDKit::ROMol cp(mol);
// storage for pieces of a molecule/s that are embedded in 2D
std::list<EmbeddedFrag> efrags;
computeInitialCoords(cp, params.coordMap, efrags, params.useRingTemplates);
#if 1
// perform random sampling here to improve the density
for (auto &eri : efrags) {
// either sample the 2D space by randomly flipping rotatable
// bonds in the structure or flip only bonds along the shortest
// path between colliding atoms - don't do both
if ((params.nSamples > 0) && (params.nFlipsPerSample > 0)) {
eri.randomSampleFlipsAndPermutations(
params.nFlipsPerSample, params.nSamples, params.sampleSeed, nullptr,
0.0, params.permuteDeg4Nodes);
} else {
eri.removeCollisionsBondFlip();
}
}
for (auto &eri : efrags) {
// if there are any remaining collisions
eri.removeCollisionsOpenAngles();
eri.removeCollisionsShortenBonds();
}
if (!params.coordMap || !params.coordMap->size()) {
if (params.canonOrient && efrags.size()) {
// if we do not have any prespecified coordinates - canonicalize
// the orientation of the fragment so that the longest axes fall
// along the x-axis etc.
for (auto &eri : efrags) {
eri.canonicalizeOrientation();
}
}
}
DepictorLocal::_shiftCoords(efrags);
#endif
// create a conformation on the molecule and copy the coordinates
auto cid = copyCoordinate(mol, efrags, params.clearConfs);
// special case for a single-atom coordMap template
if ((params.coordMap) && (params.coordMap->size() == 1)) {
auto &conf = mol.getConformer(cid);
auto cRef = params.coordMap->begin();
const auto &confPos = conf.getAtomPos(cRef->first);
auto refPos = cRef->second;
refPos.x -= confPos.x;
refPos.y -= confPos.y;
for (auto i = 0u; i < conf.getNumAtoms(); ++i) {
auto confPos = conf.getAtomPos(i);
confPos.x += refPos.x;
confPos.y += refPos.y;
conf.setAtomPos(i, confPos);
}
}
return cid;
}
//! \brief Compute the 2D coordinates such that the interatom distances
//! mimic those in a distance matrix
/*!
This function generates 2D coordinates such that the inter atom
distance mimic those specified via dmat. This is done by randomly
sampling(flipping) the rotatable bonds in the molecule and
evaluating a cost function which contains two components. The
first component is the sum of inverse of the squared inter-atom
distances, this helps in spreading the atoms far from each
other. The second component is the sum of squares of the
difference in distance between those in dmat and the generated
structure. The user can adjust the relative importance of the two
components via an adjustable parameter (see below)
ARGUMENTS:
\param mol - molecule involved in the fragment
\param dmat - the distance matrix we want to mimic, this is
symmetric N by N matrix when N is the number of
atoms in mol. All negative entries in dmat are
ignored.
\param canonOrient - canonicalize the orientation after the 2D
embedding is done
\param clearConfs - clear any previously existing conformations on
mol before adding a conformation
\param weightDistMat - A value between 0.0 and 1.0, this
determines the importance of mimicking the
inter atoms distances in dmat. (1.0 -
weightDistMat) is the weight associated to
spreading out the structure (density) in
the cost function
\param nFlipsPerSample - the number of rotatable bonds that are
randomly flipped for each sample
\param nSample - the number of samples
\param sampleSeed - seed for the random sampling process
*/
unsigned int compute2DCoordsMimicDistMat(
RDKit::ROMol &mol, const DOUBLE_SMART_PTR *dmat, bool canonOrient,
bool clearConfs, double weightDistMat, unsigned int nFlipsPerSample,
unsigned int nSamples, int sampleSeed, bool permuteDeg4Nodes, bool) {
// storage for pieces of a molecule/s that are embedded in 2D
std::list<EmbeddedFrag> efrags;
computeInitialCoords(mol, nullptr, efrags, false);
// now perform random flips of rotatable bonds so that we can sample the space
// and try to mimic the distances in dmat
std::list<EmbeddedFrag>::iterator eri;
for (auto &eri : efrags) {
eri.randomSampleFlipsAndPermutations(nFlipsPerSample, nSamples, sampleSeed,
dmat, weightDistMat, permuteDeg4Nodes);
}
if (canonOrient && efrags.size()) {
// canonicalize the orientation of the fragment so that the
// longest axes fall along the x-axis etc.
for (auto &eri : efrags) {
eri.canonicalizeOrientation();
}
}
DepictorLocal::_shiftCoords(efrags);
// create a conformation on the molecule and copy the coordinates
return copyCoordinate(mol, efrags, clearConfs);
}
namespace {
void removeAllConformersButOne(RDKit::ROMol &mol, int confId) {
std::vector<int> conformerIndicesToRemove;
for (auto confIt = mol.beginConformers(); confIt != mol.endConformers();
++confIt) {
int i = (*confIt)->getId();
if ((confId != -1 && i == confId) ||
(confId == -1 && confIt == mol.beginConformers())) {
continue;
}
conformerIndicesToRemove.push_back(i);
}
for (auto i : conformerIndicesToRemove) {
mol.removeConformer(i);
}
CHECK_INVARIANT(mol.getNumConformers() == 1, "");
mol.getConformer().setId(0);
}
} // namespace
//! \brief Compute 2D coordinates where a piece of the molecule is
/// hard or soft-constrained to have the same coordinates as a reference.
/// Correspondences between reference and molecule atom indices
/// are determined by refMatchVect.
void generateDepictionMatching2DStructure(
RDKit::ROMol &mol, const RDKit::ROMol &reference,
const RDKit::MatchVectType &refMatchVect, int confId,
const ConstrainedDepictionParams &p) {
if (refMatchVect.size() > reference.getNumAtoms()) {
throw DepictException(
"When a refMatchVect is provided, it must have size "
"<= number of atoms in the reference");
}
for (const auto &mv : refMatchVect) {
if (mv.first > static_cast<int>(reference.getNumAtoms())) {
throw DepictException(
"Reference atom index in refMatchVect out of range");
}
if (mv.second > static_cast<int>(mol.getNumAtoms())) {
throw DepictException("Molecule atom index in refMatchVect out of range");
}
}
bool hasExistingCoords = mol.getNumConformers() > 0;
bool shouldClearWedgingInfo = p.adjustMolBlockWedging && !hasExistingCoords;
bool shouldInvertWedgingIfRequired = false;
RDGeom::Transform3D trans;
if (p.alignOnly) {
if (!hasExistingCoords) {
compute2DCoords(mol, nullptr, false, true, 0, 0, 0, false, p.forceRDKit,
p.useRingTemplates);
}
RDKit::MatchVectType atomMap(refMatchVect.size());
std::transform(
refMatchVect.begin(), refMatchVect.end(), atomMap.begin(),
[](auto &pair) { return std::make_pair(pair.second, pair.first); });
RDKit::MolAlign::getAlignmentTransform(mol, reference, trans,
p.existingConfId, confId, &atomMap);
MolTransforms::transformConformer(mol.getConformer(p.existingConfId),
trans);
removeAllConformersButOne(mol, p.existingConfId);
if (!shouldClearWedgingInfo) {
shouldInvertWedgingIfRequired = p.adjustMolBlockWedging;
}
} else {
RDGeom::INT_POINT2D_MAP coordMap;
const RDKit::Conformer &refConf = reference.getConformer(confId);
for (const auto &mv : refMatchVect) {
const auto &pt3 = refConf.getAtomPos(mv.first);
coordMap[mv.second] = RDGeom::Point2D(pt3.x, pt3.y);
}
auto newConfId = compute2DCoords(
mol, &coordMap, false /* canonOrient */,
!(p.adjustMolBlockWedging && hasExistingCoords) /* clearConfs */, 0, 0,
0, false, p.forceRDKit, p.useRingTemplates);
if (p.adjustMolBlockWedging) {
// we need to clear the existing wedging information if:
// 1. the original molecule had no coordinates to start with
// (in that case it should already have no wedging info either, anyway)
// 2. there is a match and wedges are outside the constrained scaffold
constexpr double RMSD_THRESHOLD = 1.e-2;
constexpr double MSD_THRESHOLD = RMSD_THRESHOLD * RMSD_THRESHOLD;
if (!shouldClearWedgingInfo) {
boost::dynamic_bitset<> molMatchingIndices(mol.getNumAtoms());
for (const auto &pair : refMatchVect) {
molMatchingIndices.set(pair.second);
}
// if any of the bonds that have wedging information from the molblock
// has at least one atom which is not part of the scaffold, we cannot
// preserve wedging information
auto molBonds = mol.bonds();
shouldClearWedgingInfo = std::any_of(
molBonds.begin(), molBonds.end(),
[&molMatchingIndices](const auto b) {
return (
(b->hasProp(RDKit::common_properties::_MolFileBondStereo) ||
b->hasProp(RDKit::common_properties::_MolFileBondCfg)) &&
(!molMatchingIndices.test(b->getBeginAtomIdx()) ||
!molMatchingIndices.test(b->getEndAtomIdx())));
});
}
if (!shouldClearWedgingInfo) {
// check that scaffold coordinates have not changed, which may
// happen when using CoordGen
const auto &molPos = mol.getConformer(newConfId).getPositions();
const auto &refPos = refConf.getPositions();
shouldClearWedgingInfo = std::any_of(
refMatchVect.begin(), refMatchVect.end(),
[&molPos, &refPos, MSD_THRESHOLD](const auto &pair) {
return (molPos.at(pair.second) - refPos.at(pair.first))
.lengthSq() > MSD_THRESHOLD;
});
}
// final check: we still might need to invert wedging if the molecule
// has flipped to match the scaffold
if (!shouldClearWedgingInfo) {
RDKit::MatchVectType identityMatch(refMatchVect.size());
std::transform(refMatchVect.begin(), refMatchVect.end(),
identityMatch.begin(), [](const auto &pair) {
return std::make_pair(pair.second, pair.second);
});
auto rmsd = RDKit::MolAlign::getAlignmentTransform(
mol, mol, trans, newConfId, p.existingConfId, &identityMatch);
// this should not happen as we checked that previously, but we are
// notoriously paranoid
if (rmsd > RMSD_THRESHOLD) {
shouldClearWedgingInfo = true;
} else {
shouldInvertWedgingIfRequired = true;
}
}
}
if (hasExistingCoords) {
removeAllConformersButOne(mol, newConfId);
}
}
if (shouldClearWedgingInfo) {
RDKit::Chirality::clearMolBlockWedgingInfo(mol);
} else if (shouldInvertWedgingIfRequired) {
invertWedgingIfMolHasFlipped(mol, trans);
}
}
// Overload
void generateDepictionMatching2DStructure(
RDKit::ROMol &mol, const RDKit::ROMol &reference,
const RDKit::MatchVectType &refMatchVect, int confId, bool forceRDKit) {
ConstrainedDepictionParams p;
p.forceRDKit = forceRDKit;
generateDepictionMatching2DStructure(mol, reference, refMatchVect, confId, p);
}
//! \brief Compute 2D coordinates where a piece of the molecule is
/// hard or soft-constrained to have the same coordinates as a reference.
RDKit::MatchVectType generateDepictionMatching2DStructure(
RDKit::ROMol &mol, const RDKit::ROMol &reference, int confId,
const RDKit::ROMol *referencePattern,
const ConstrainedDepictionParams &params) {
// reference with added Hs
std::unique_ptr<RDKit::RWMol> referenceHs;
// mol with added Hs
std::unique_ptr<RDKit::RWMol> molHs;
// query with adjusted dummies and bond orders
std::unique_ptr<RDKit::RWMol> queryAdj;
// MatchVectType mapping reference atom indices to mol atom indices
RDKit::MatchVectType matchVect;
// holds multiple matches between reference atom indices
// and referencePattern atom indices
std::vector<RDKit::MatchVectType> patternToRefMatches;
// holds single match between reference atom indices
// and referencePattern atom indices
RDKit::MatchVectType patternToRefMatch;
// reference to best single match between reference atom indices
// and referencePattern atom indices
auto &bestPatternToRefMatch = patternToRefMatch;
// reference to referencePattern (if non-null) or reference
const RDKit::ROMol &query =
(referencePattern ? *referencePattern : reference);
// mapping of referencePattern atom indices to reference atom indices
std::vector<int> patternToRefMapping(query.getNumAtoms(), -1);
// reference to mol or, if allowRGroups is true, molHs
const RDKit::ROMol *prbMol = &mol;
// reference to query or, if allowRGroups is true, queryAdj
const RDKit::ROMol *refMol = &query;
// local copy of ConstrainedDepictionParams
ConstrainedDepictionParams p(params);
// we do not need the allowRGroups logic if there are no
// terminal dummy atoms
p.allowRGroups = p.allowRGroups && hasTerminalRGroupOrQueryHydrogen(query);
std::unique_ptr<RDKit::ROMol> reducedQuery;
if (p.allowRGroups) {
molHs.reset(new RDKit::RWMol(mol));
RDKit::MolOps::addHs(*molHs);
queryAdj.reset(new RDKit::RWMol(query));
reducedQuery = prepareTemplateForRGroups(*queryAdj);
prbMol = static_cast<const RDKit::ROMol *>(molHs.get());
refMol = reducedQuery ? reducedQuery.get()
: static_cast<const RDKit::ROMol *>(queryAdj.get());
}
if (referencePattern) {
// if referencePattern has more atoms than reference and allowRGroups
// is true, then add Hs to reference and find the mapping that maps the
// largest number of heavy atoms to referencePattern
if (p.allowRGroups) {
referenceHs.reset(new RDKit::RWMol(reference));
RDKit::MolOps::addHs(*referenceHs);
CHECK_INVARIANT(queryAdj, "");
patternToRefMatches = RDKit::SubstructMatch(*referenceHs, *refMol);
if (reducedQuery) {
reducedToFullMatches(*reducedQuery, *referenceHs, patternToRefMatches);
}
if (!patternToRefMatches.empty()) {
bestPatternToRefMatch = RDKit::getMostSubstitutedCoreMatch(
*referenceHs, *queryAdj, patternToRefMatches);
}
// otherwise do a simple SubstructMatch
} else {
RDKit::SubstructMatch(reference, *referencePattern,
bestPatternToRefMatch);
}
// either way, we should now have a single match
if (bestPatternToRefMatch.empty()) {
throw DepictException("Reference pattern does not map to reference.");
}
int numRefAtoms = reference.getNumAtoms();
for (auto &pair : bestPatternToRefMatch) {
// skip indices corresponding to added Hs
if (p.allowRGroups && pair.second >= numRefAtoms) {
continue;
}
CHECK_INVARIANT(
pair.first >= 0 &&
pair.first < static_cast<int>(patternToRefMapping.size()),
"");
patternToRefMapping[pair.first] = pair.second;
}
} else {
// 1-1 mapping as we use reference atom indices directly
std::iota(patternToRefMapping.begin(), patternToRefMapping.end(), 0);
}
if (p.alignOnly) {
// we only do a rigid-body alignment of the molecule onto the reference
std::vector<RDKit::MatchVectType> matches;
if (SubstructMatch(*prbMol, *refMol, matches, false)) {
if (p.allowRGroups) {
// we want to match the max number of R-groups to heavy atoms
if (reducedQuery) {
reducedToFullMatches(*reducedQuery, *prbMol, matches);
}
matches =
sortMatchesByDegreeOfCoreSubstitution(*prbMol, *queryAdj, matches);
int maxMatchedHeavies = -1;
int maxPrunedMatchSize = -1;
std::vector<RDKit::MatchVectType> prunedMatches;
prunedMatches.reserve(matches.size());
int numMolAtoms = mol.getNumAtoms();
for (const auto &match : matches) {
// we want to prune from the match any added hydrogens
// as they were not originally part of the molecule
int nMatchedHeavies = 0;
RDKit::MatchVectType prunedMatch;
prunedMatch.reserve(match.size());
for (const auto &pair : match) {
const auto refAtom = queryAdj->getAtomWithIdx(pair.first);
if (isAtomTerminalRGroupOrQueryHydrogen(refAtom)) {
// skip the match if it is an added H
if (pair.second >= numMolAtoms) {
continue;
}
++nMatchedHeavies;
}
auto refIdx = patternToRefMapping.at(pair.first);
if (refIdx == -1) {
continue;
}
prunedMatch.push_back(std::move(pair));
}
if (nMatchedHeavies < maxMatchedHeavies) {
break;
}
maxMatchedHeavies = nMatchedHeavies;
int prunedMatchSize = prunedMatch.size();
if (prunedMatchSize > maxPrunedMatchSize) {
maxPrunedMatchSize = prunedMatchSize;
prunedMatches.clear();
}
if (prunedMatchSize == maxPrunedMatchSize) {
prunedMatches.push_back(std::move(prunedMatch));
}
}
matches = std::move(prunedMatches);
}
// matches maps reference atom idx to mol atom idx
// but getBestAlignmentTransform needs the reverse
// while we do the swap, we also map pattern indices
// back to reference indices
std::for_each(
matches.begin(), matches.end(), [&patternToRefMapping](auto &match) {
std::for_each(match.begin(), match.end(),
[&patternToRefMapping](auto &pair) {
auto refIdx = patternToRefMapping.at(pair.first);
CHECK_INVARIANT(refIdx != -1, "");
pair.first = pair.second;
pair.second = refIdx;
});
});
// if the molecule does not already have coordinates, we
// need to generate some before attempting the alignment
// and clear any existing wedging info if requested
if (!mol.getNumConformers()) {
compute2DCoords(mol, nullptr, false, true, 0, 0, 0, false, p.forceRDKit,
p.useRingTemplates);
if (p.adjustMolBlockWedging) {
RDKit::Chirality::clearMolBlockWedgingInfo(mol);
p.adjustMolBlockWedging = false;
}
}
RDGeom::Transform3D trans;
// cap the effort we are willing to make to get the best alignment
constexpr int MAX_MATCHES = 1000;
RDKit::MolAlign::getBestAlignmentTransform(mol, reference, trans,
matchVect, p.existingConfId,
confId, matches, MAX_MATCHES);
// swap again as we want to return (reference atom idx, mol atom idx)
std::for_each(matchVect.begin(), matchVect.end(),
[](auto &pair) { std::swap(pair.first, pair.second); });
MolTransforms::transformConformer(mol.getConformer(p.existingConfId),
trans);
removeAllConformersButOne(mol, p.existingConfId);
if (p.adjustMolBlockWedging) {
invertWedgingIfMolHasFlipped(mol, trans);
}
}
} else {
// we do a full coordinate rebuild around the constrained reference
if (p.allowRGroups) {
std::vector<RDKit::MatchVectType> matches;
SubstructMatch(*prbMol, *refMol, matches, false);
if (!matches.empty()) {
if (reducedQuery) {
reducedToFullMatches(*reducedQuery, *prbMol, matches);
}
int numMolAtoms = mol.getNumAtoms();
for (const auto &pair :
getMostSubstitutedCoreMatch(*prbMol, *queryAdj, matches)) {
if (pair.second < numMolAtoms &&
patternToRefMapping.at(pair.first) != -1) {
matchVect.push_back(std::move(pair));
}
}
}
} else {
RDKit::SubstructMatch(*prbMol, *refMol, matchVect);
}
if (!matchVect.empty()) {
for (auto &pair : matchVect) {
pair.first = patternToRefMapping.at(pair.first);
}
generateDepictionMatching2DStructure(mol, reference, matchVect, confId,
p);
}
}
if (matchVect.empty()) {
if (p.acceptFailure) {
// if we accept failure, we generate a standard set of
// coordinates and clear any existing wedging info if requested
compute2DCoords(mol, nullptr, false, true, 0, 0, 0, false, p.forceRDKit,
p.useRingTemplates);
if (p.adjustMolBlockWedging) {
RDKit::Chirality::clearMolBlockWedgingInfo(mol);
}
} else {
throw DepictException("Substructure match with reference not found.");
}
}
return matchVect;
}
// Overload
RDKit::MatchVectType generateDepictionMatching2DStructure(
RDKit::ROMol &mol, const RDKit::ROMol &reference, int confId,
const RDKit::ROMol *referencePattern, bool acceptFailure, bool forceRDKit,
bool allowOptionalAttachments) {
ConstrainedDepictionParams p;
p.acceptFailure = acceptFailure;
p.forceRDKit = forceRDKit;
p.allowRGroups = allowOptionalAttachments;
return generateDepictionMatching2DStructure(mol, reference, confId,
referencePattern, p);
}
//! \brief Generate a 2D depiction for a molecule where all or part of
// it mimics the coordinates of a 3D reference structure.
void generateDepictionMatching3DStructure(RDKit::ROMol &mol,
const RDKit::ROMol &reference,
int confId,
RDKit::ROMol *referencePattern,
bool acceptFailure, bool forceRDKit) {
auto num_ats = mol.getNumAtoms();
if (!referencePattern && reference.getNumAtoms() < num_ats) {
if (acceptFailure) {
compute2DCoords(mol);
return;
} else {
throw DepictException(
"Reference molecule not compatible with target molecule.");
}
}
std::vector<int> mol_to_ref(num_ats, -1);
if (referencePattern && referencePattern->getNumAtoms()) {
RDKit::MatchVectType molMatchVect, refMatchVect;
RDKit::SubstructMatch(mol, *referencePattern, molMatchVect);
RDKit::SubstructMatch(reference, *referencePattern, refMatchVect);
if (molMatchVect.empty() || refMatchVect.empty()) {
if (acceptFailure) {
compute2DCoords(mol);
return;
} else {
throw DepictException(
"Reference pattern didn't match molecule or reference.");
}
}
for (size_t i = 0; i < molMatchVect.size(); ++i) {
mol_to_ref[molMatchVect[i].second] = refMatchVect[i].second;
}
} else {
for (unsigned int i = 0; i < num_ats; ++i) {
mol_to_ref[i] = i;
}
}
const RDKit::Conformer &conf = reference.getConformer(confId);
// the distance matrix is a triangular representation
DOUBLE_SMART_PTR dmat(new double[num_ats * (num_ats - 1) / 2]);
// negative distances are ignored, so initialise to -1.0 so subset by
// referencePattern works.
std::fill(dmat.get(), dmat.get() + num_ats * (num_ats - 1) / 2, -1.0);
for (unsigned int i = 0; i < num_ats; ++i) {
if (-1 == mol_to_ref[i]) {
continue;
}
RDGeom::Point3D cds_i = conf.getAtomPos(i);
for (unsigned int j = i + 1; j < num_ats; ++j) {
if (-1 == mol_to_ref[j]) {
continue;
}
RDGeom::Point3D cds_j = conf.getAtomPos(mol_to_ref[j]);
dmat[(j * (j - 1) / 2) + i] = (cds_i - cds_j).length();
}
}
compute2DCoordsMimicDistMat(mol, &dmat, false, true, 0.5, 3, 100, 25, true,
forceRDKit);
}
void straightenDepiction(RDKit::ROMol &mol, int confId, bool minimizeRotation) {
if (!mol.getNumBonds()) {
return;
}
constexpr double RAD2DEG = 180. / M_PI;
constexpr double DEG2RAD = M_PI / 180.;
constexpr double ALMOST_ZERO = 1.e-5;
constexpr double INCR_DEG = 30.;
constexpr double HALF_INCR_DEG = 0.5 * INCR_DEG;
constexpr double QUARTER_INCR_DEG = 0.25 * INCR_DEG;
auto &conf = mol.getConformer(confId);
auto &pos = conf.getPositions();
std::unordered_map<int, DepictorLocal::ThetaBin> thetaBins;
for (const auto b : mol.bonds()) {
auto bi = b->getBeginAtomIdx();
auto ei = b->getEndAtomIdx();
auto bv = pos.at(bi) - pos.at(ei);
bv.x = (bv.x < 0.) ? std::min(-ALMOST_ZERO, bv.x)
: std::max(ALMOST_ZERO, bv.x);
auto theta = RAD2DEG * atan(bv.y / bv.x);
auto d_theta = fmod(-theta, INCR_DEG);
if (fabs(d_theta) > HALF_INCR_DEG) {
d_theta -= DepictorLocal::copySign(INCR_DEG, d_theta, ALMOST_ZERO);
}
int thetaKey = static_cast<int>(
d_theta + DepictorLocal::copySign(0.5, d_theta, ALMOST_ZERO));
auto &thetaBin = thetaBins[thetaKey];
thetaBin.d_thetaAvg += d_theta;
thetaBin.thetaValues.push_back(theta);
}
CHECK_INVARIANT(!thetaBins.empty(), "");
double d_thetaSmallest = std::numeric_limits<double>::max();
for (auto &it : thetaBins) {
auto &thetaBin = it.second;
thetaBin.d_thetaAvg /= static_cast<double>(thetaBin.thetaValues.size());
if (fabs(thetaBin.d_thetaAvg) < fabs(d_thetaSmallest)) {
d_thetaSmallest = thetaBin.d_thetaAvg;
}
}
const auto &minRotationBin =
std::max_element(
thetaBins.begin(), thetaBins.end(),
[](const auto &a, const auto &b) {
const auto &aBin = a.second;
const auto &bBin = b.second;
return (aBin.thetaValues.size() < bBin.thetaValues.size() ||
(aBin.thetaValues.size() == bBin.thetaValues.size() &&
fabs(aBin.d_thetaAvg) > fabs(bBin.d_thetaAvg)));
})
->second;
double d_thetaMin = minRotationBin.d_thetaAvg;
// unless we want to preserve as much as possible the initial orientation,
// we try to orient the molecule such that the majority of bonds have
// an angle of 30 or 90 degrees with the X axis
if (!minimizeRotation) {
unsigned int count60vs30[2] = {0, 0};
for (auto theta : minRotationBin.thetaValues) {
auto absTheta = fabs(theta + d_thetaMin);
// Do not count 0 as multiple of 60 degrees
if (absTheta < ALMOST_ZERO) {
continue;
}
auto idx = static_cast<unsigned int>((absTheta + 0.5) / INCR_DEG) % 2;
CHECK_INVARIANT(idx < 2, "");
++count60vs30[idx];
}
if (count60vs30[0] > count60vs30[1]) {
d_thetaMin -= DepictorLocal::copySign(INCR_DEG, d_thetaMin, ALMOST_ZERO);
}
} else if (fabs(d_thetaSmallest) < ALMOST_ZERO ||
(fabs(d_thetaSmallest) < fabs(d_thetaMin) &&
fabs(d_thetaMin) > QUARTER_INCR_DEG)) {
d_thetaMin = d_thetaSmallest;
}
if (fabs(d_thetaMin) > ALMOST_ZERO) {
d_thetaMin *= DEG2RAD;
RDGeom::Transform3D trans;
trans.SetRotation(d_thetaMin, RDGeom::Z_Axis);
MolTransforms::transformConformer(conf, trans);
}
}
double normalizeDepiction(RDKit::ROMol &mol, int confId, int canonicalize,
double scaleFactor) {
constexpr double SCALE_FACTOR_THRESHOLD = 1.e-5;
if (!mol.getNumBonds()) {
return -1.;
}
auto &conf = mol.getConformer(confId);
if (scaleFactor < 0.0) {
constexpr double RDKIT_BOND_LEN = 1.5;
int mostCommonBondLengthInt = -1;
unsigned int maxCount = 0;
std::unordered_map<int, unsigned int> binnedBondLengths;
for (const auto b : mol.bonds()) {
int bondLength =
static_cast<int>(MolTransforms::getBondLength(
conf, b->getBeginAtomIdx(), b->getEndAtomIdx()) *
10.0 +
0.5);
auto it = binnedBondLengths.find(bondLength);
if (it == binnedBondLengths.end()) {
it = binnedBondLengths.emplace(bondLength, 0U).first;
}
++it->second;
if (it->second > maxCount) {
maxCount = it->second;
mostCommonBondLengthInt = it->first;
}
}
if (mostCommonBondLengthInt > 0) {
double mostCommonBondLength =
static_cast<double>(mostCommonBondLengthInt) * 0.1;
scaleFactor = RDKIT_BOND_LEN / mostCommonBondLength;
}
}
std::unique_ptr<RDGeom::Transform3D> canonTrans;
auto ctd = MolTransforms::computeCentroid(conf);
if (canonicalize) {
canonTrans.reset(MolTransforms::computeCanonicalTransform(conf, &ctd));
if (canonicalize < 0) {
RDGeom::Transform3D rotate90;
rotate90.SetRotation(0., 1., RDGeom::Point3D(0., 0., 1.));
*canonTrans *= rotate90;
}
} else {
canonTrans.reset(new RDGeom::Transform3D());
canonTrans->SetTranslation(-ctd);
}
bool isScaleFactorSane = (scaleFactor > SCALE_FACTOR_THRESHOLD);
if (isScaleFactorSane && fabs(scaleFactor - 1.0) > SCALE_FACTOR_THRESHOLD) {
RDGeom::Transform3D trans;
trans.setVal(0, 0, scaleFactor);
trans.setVal(1, 1, scaleFactor);
if (canonTrans) {
trans *= *canonTrans;
}
MolTransforms::transformConformer(conf, trans);
} else if (canonTrans) {
MolTransforms::transformConformer(conf, *canonTrans);
}
if (!isScaleFactorSane) {
scaleFactor = -1.;
}
return scaleFactor;
}
} // namespace RDDepict
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