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//
// Copyright (C) David Cosgrove 2025.
//
// @@ 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 <GraphMol/Chirality.h>
#include <GraphMol/RWMol.h>
#include <GraphMol/EnumerateStereoisomers/Flippers.h>
#include <GraphMol/SmilesParse/SmilesWrite.h>
namespace RDKit {
namespace EnumerateStereoisomers {
namespace details {
AtomFlipper::AtomFlipper(RWMol &mol, const Chirality::StereoInfo &si)
: Flipper() {
dp_atom = mol.getAtomWithIdx(si.centeredOn);
}
void AtomFlipper::flip(bool flag) {
if (flag) {
dp_atom->setChiralTag(Atom::ChiralType::CHI_TETRAHEDRAL_CW);
} else {
dp_atom->setChiralTag(Atom::ChiralType::CHI_TETRAHEDRAL_CCW);
}
}
BondFlipper::BondFlipper(RWMol &mol, const Chirality::StereoInfo &si)
: Flipper() {
dp_bond = mol.getBondWithIdx((si.centeredOn));
auto stereoAtoms = dp_bond->getStereoAtoms();
if (stereoAtoms.empty()) {
if (si.controllingAtoms[0] != Chirality::StereoInfo::NOATOM &&
si.controllingAtoms[2] != Chirality::StereoInfo::NOATOM) {
dp_bond->setStereoAtoms(si.controllingAtoms[0], si.controllingAtoms[2]);
} else {
dp_bond = nullptr;
}
}
}
void BondFlipper::flip(bool flag) {
if (flag) {
dp_bond->setStereo(Bond::STEREOCIS);
} else {
dp_bond->setStereo(Bond::STEREOTRANS);
}
}
StereoGroupFlipper::StereoGroupFlipper(const StereoGroup &sg) : Flipper() {
for (auto a : sg.getAtoms()) {
d_original_parities.emplace_back(std::make_pair(a, a->getChiralTag()));
}
}
void StereoGroupFlipper::flip(bool flag) {
if (flag) {
for (auto &a : d_original_parities) {
a.first->setChiralTag(a.second);
}
} else {
for (auto &[atom, chiralType] : d_original_parities) {
if (chiralType == Atom::ChiralType::CHI_TETRAHEDRAL_CW) {
atom->setChiralTag(Atom::ChiralType::CHI_TETRAHEDRAL_CCW);
} else if (chiralType == Atom::ChiralType::CHI_TETRAHEDRAL_CCW) {
atom->setChiralTag(Atom::CHI_TETRAHEDRAL_CW);
}
}
}
}
AtropisomerFlipper::AtropisomerFlipper(RWMol &mol,
const Chirality::StereoInfo &si) {
dp_bond = mol.getBondWithIdx(si.centeredOn);
d_ctrlAtoms =
std::vector<unsigned int>{si.controllingAtoms[0], si.controllingAtoms[1],
si.controllingAtoms[2], si.controllingAtoms[3]};
}
void AtropisomerFlipper::flip(bool flag) {
auto mol = dp_bond->getOwningMol();
auto b1 = mol.getBondBetweenAtoms(dp_bond->getBeginAtomIdx(), d_ctrlAtoms[0]);
auto b2 = mol.getBondBetweenAtoms(dp_bond->getBeginAtomIdx(), d_ctrlAtoms[1]);
auto b3 = mol.getBondBetweenAtoms(dp_bond->getEndAtomIdx(), d_ctrlAtoms[2]);
auto b4 = mol.getBondBetweenAtoms(dp_bond->getEndAtomIdx(), d_ctrlAtoms[3]);
b3->setBondDir(Bond::BondDir::NONE);
b4->setBondDir(Bond::BondDir::NONE);
if (!flag) {
dp_bond->setStereo(Bond::STEREOATROPCW);
if (d_ctrlAtoms[0] < d_ctrlAtoms[1]) {
b1->setBondDir(Bond::BondDir::BEGINDASH);
b2->setBondDir(Bond::BondDir::NONE);
} else {
b2->setBondDir(Bond::BondDir::BEGINDASH);
b1->setBondDir(Bond::BondDir::NONE);
}
} else {
dp_bond->setStereo(Bond::STEREOATROPCCW);
if (d_ctrlAtoms[0] < d_ctrlAtoms[1]) {
b1->setBondDir(Bond::BondDir::BEGINWEDGE);
b2->setBondDir(Bond::BondDir::NONE);
} else {
b2->setBondDir(Bond::BondDir::BEGINWEDGE);
b1->setBondDir(Bond::BondDir::NONE);
}
}
}
} // namespace details
} // namespace EnumerateStereoisomers
} // namespace RDKit
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