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rdkit/Code/GraphMol/AdjustQuery.cpp
greg landrum a068a18a53 all tests now passing
2020-12-08 15:39:45 +01:00

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//
// Copyright (c) 2015-2020 Greg Landrum
//
// @@ 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/GraphMol.h>
#include <GraphMol/QueryAtom.h>
#include <GraphMol/QueryBond.h>
#include <GraphMol/MolOps.h>
#include <GraphMol/QueryOps.h>
#include <GraphMol/AtomIterators.h>
#include <GraphMol/BondIterators.h>
#include <RDGeneral/BoostStartInclude.h>
#include <boost/property_tree/ptree.hpp>
#include <boost/property_tree/json_parser.hpp>
#include <boost/algorithm/string.hpp>
#include <boost/tokenizer.hpp>
#include <RDGeneral/BoostEndInclude.h>
#include <vector>
#include <algorithm>
namespace RDKit {
namespace {
bool isMapped(const Atom *atom) {
return atom->hasProp(common_properties::molAtomMapNumber);
}
} // namespace
namespace MolOps {
namespace {
typedef boost::tokenizer<boost::char_separator<char>> tokenizer;
unsigned int parseWhichString(const std::string &txt) {
unsigned int res = MolOps::ADJUST_IGNORENONE;
boost::char_separator<char> sep("|");
tokenizer tokens(txt, sep);
for (const auto &token : tokens) {
if (token == "IGNORENONE") {
res |= MolOps::ADJUST_IGNORENONE;
} else if (token == "IGNORERINGS") {
res |= MolOps::ADJUST_IGNORERINGS;
} else if (token == "IGNORECHAINS") {
res |= MolOps::ADJUST_IGNORECHAINS;
} else if (token == "IGNOREDUMMIES") {
res |= MolOps::ADJUST_IGNOREDUMMIES;
} else if (token == "IGNORENONDUMMIES") {
res |= MolOps::ADJUST_IGNORENONDUMMIES;
} else if (token == "IGNOREALL") {
res |= MolOps::ADJUST_IGNOREALL;
} else {
std::string msg = "Unknown flag value: '" + token + "'. Flags ignored.";
throw ValueErrorException(msg);
}
}
return res;
}
void adjustConjugatedFiveRings(RWMol &mol) {
/*
The idea here is to allow conjugated five-rings to match either aromatic or
aliphatic rings
five-rings which contain at least 3 conjugated bonds have all of their
non-query bonds replaced with a SINGLE|DOUBLE|AROMATIC query.
*/
std::vector<Bond::BondType> bondTypesToModify = {
Bond::BondType::SINGLE, Bond::BondType::DOUBLE, Bond::BondType::AROMATIC};
if (!mol.getRingInfo()->isInitialized()) {
MolOps::symmetrizeSSSR(mol);
}
for (auto ring : mol.getRingInfo()->bondRings()) {
// only consider 5-rings with at least 3 conjugated bonds
if (ring.size() != 5) {
continue;
}
unsigned int nconj = 0;
for (auto bi : ring) {
const auto bond = mol.getBondWithIdx(bi);
if (bond->getIsConjugated()) {
++nconj;
if (nconj >= 3) {
break;
}
}
}
if (nconj < 3) {
continue;
}
// now make the adjustments
QueryBond qb;
qb.setQuery(makeSingleOrDoubleOrAromaticBondQuery());
for (auto bi : ring) {
const auto bond = mol.getBondWithIdx(bi);
if (std::find(bondTypesToModify.begin(), bondTypesToModify.end(),
bond->getBondType()) != bondTypesToModify.end()) {
if (bond->hasQuery()) {
BOOST_LOG(rdWarningLog)
<< "adjustConjugatedFiveRings: replacing a bond "
"that already has a query"
<< std::endl;
}
mol.replaceBond(bi, &qb);
}
}
}
}
void adjustSingleBondsFromAromaticAtoms(RWMol &mol, bool toDegreeOneNeighbors,
bool betweenAromaticAtoms) {
/*
The idea here is to allow single bonds coming from aromatic atoms to match
aromatic bonds under particular circumstances. The conditions are:
1. toDegreeOneNeighbors: [D1]-[a] -> [D1]-,:[a]
2. betweenAromaticAtoms: [a]-[a] -> [a]-,:[a]
*/
if (!toDegreeOneNeighbors && !betweenAromaticAtoms) {
return;
}
QueryBond qb;
qb.setQuery(makeSingleOrAromaticBondQuery());
if (!mol.getRingInfo()->isInitialized()) {
MolOps::symmetrizeSSSR(mol);
}
for (auto bond : mol.bonds()) {
const auto bAt = bond->getBeginAtom();
const auto eAt = bond->getEndAtom();
if (!bond->hasQuery() && bond->getBondType() == Bond::BondType::SINGLE &&
(bAt->getIsAromatic() || eAt->getIsAromatic())) {
if (toDegreeOneNeighbors &&
(bAt->getIsAromatic() ^ eAt->getIsAromatic())) {
if ((bAt->getIsAromatic() && eAt->getDegree() == 1) ||
(eAt->getIsAromatic() && bAt->getDegree() == 1)) {
mol.replaceBond(bond->getIdx(), &qb);
}
} else if (betweenAromaticAtoms && bAt->getIsAromatic() &&
eAt->getIsAromatic()) {
mol.replaceBond(bond->getIdx(), &qb);
}
}
}
}
void setMDLAromaticity(RWMol &mol) {
/*
The idea here is to make aromatic 5-rings that contain an "A" atom in the CTAB
match both aromatic and aliphatic rings.
Schematically, this converts the ring from:
["A"]1:c:c:c:c:1
to:
["A"]1-,:c=,:c-,:c=,:c-,:1
Note that "A" is an A atom from a CTAB, not a SMARTS aliphatic query
*/
// it would be simpler to use the substructure matcher for this, but we can't
// use SubstructMatch in the core GraphMol lib
if (!mol.getRingInfo()->isInitialized()) {
MolOps::symmetrizeSSSR(mol);
}
for (auto ring : mol.getRingInfo()->atomRings()) {
if (ring.size() != 5) {
continue;
}
bool keepIt = true;
size_t dummy = ring.size() + 1;
for (size_t i = 0; i < ring.size(); ++i) {
auto ai = ring[i];
const auto atom = mol.getAtomWithIdx(ai);
if (!atom->getIsAromatic()) {
// we only do fully aromatic rings:
keepIt = false;
break;
} else if (atom->getAtomicNum() == 0 && atom->hasQuery() &&
atom->getQuery()->getTypeLabel() == "A") {
if (dummy >= ring.size()) {
dummy = i;
} else {
// second dummy encountered, we won't do this ring.
keepIt = false;
break;
}
} else if (atom->getAtomicNum() != 6) {
// we only do rings consisting solely of C and *
keepIt = false;
break;
}
// we can't handle rings that have query bonds already:
auto oidx = ring[4];
if (i > 0) {
oidx = ring[i - 1];
}
auto bond = mol.getBondBetweenAtoms(ring[i], oidx);
ASSERT_INVARIANT(bond, "expected bond not found");
if (bond->hasQuery()) {
keepIt = false;
break;
}
}
if (keepIt && dummy < ring.size()) {
// we think about the 5-ring in three layers:
// layer 0: the dummy
// layer 1: the two atoms connected to the dummy
// layer 2: the two atoms not connected to the dummy
auto l0 = ring[dummy];
std::vector<int> l1;
std::vector<int> l2;
for (auto ai : ring) {
if (ai == l0) {
continue;
} else if (mol.getBondBetweenAtoms(ai, l0)) {
l1.push_back(ai);
} else {
l2.push_back(ai);
}
}
ASSERT_INVARIANT(l1.size() == 2, "bad layer 1 size");
ASSERT_INVARIANT(l2.size() == 2, "bad layer 2 size");
QueryBond qbSingleAromatic;
{
BOND_OR_QUERY *q = new BOND_OR_QUERY;
q->addChild(QueryBond::QUERYBOND_QUERY::CHILD_TYPE(
makeBondOrderEqualsQuery(Bond::SINGLE)));
q->addChild(QueryBond::QUERYBOND_QUERY::CHILD_TYPE(
makeBondOrderEqualsQuery(Bond::AROMATIC)));
q->setDescription("BondOr");
qbSingleAromatic.setQuery(q);
}
QueryBond qbDoubleAromatic;
{
BOND_OR_QUERY *q = new BOND_OR_QUERY;
q->addChild(QueryBond::QUERYBOND_QUERY::CHILD_TYPE(
makeBondOrderEqualsQuery(Bond::DOUBLE)));
q->addChild(QueryBond::QUERYBOND_QUERY::CHILD_TYPE(
makeBondOrderEqualsQuery(Bond::AROMATIC)));
q->setDescription("BondOr");
qbDoubleAromatic.setQuery(q);
}
for (auto ai : l1) {
// l0 - l1 bonds:
auto bond = mol.getBondBetweenAtoms(ai, l0);
ASSERT_INVARIANT(bond, "expected l0-l1 bond not found");
mol.replaceBond(bond->getIdx(), &qbSingleAromatic);
// l1 - l2 bonds:
bond = mol.getBondBetweenAtoms(ai, l2[0]);
if (!bond) {
bond = mol.getBondBetweenAtoms(ai, l2[1]);
}
ASSERT_INVARIANT(bond, "expected l1-l2 bond not found");
mol.replaceBond(bond->getIdx(), &qbDoubleAromatic);
}
// l2 - l2 bond:
auto bond = mol.getBondBetweenAtoms(l2[0], l2[1]);
ASSERT_INVARIANT(bond, "expected l2-l2 bond not found");
mol.replaceBond(bond->getIdx(), &qbSingleAromatic);
}
}
}
} // namespace
void parseAdjustQueryParametersFromJSON(MolOps::AdjustQueryParameters &p,
const std::string &json) {
PRECONDITION(!json.empty(), "empty JSON provided");
std::istringstream ss;
ss.str(json);
boost::property_tree::ptree pt;
boost::property_tree::read_json(ss, pt);
p.adjustDegree = pt.get("adjustDegree", p.adjustDegree);
p.adjustRingCount = pt.get("adjustRingCount", p.adjustRingCount);
p.makeDummiesQueries = pt.get("makeDummiesQueries", p.makeDummiesQueries);
p.aromatizeIfPossible = pt.get("aromatizeIfPossible", p.aromatizeIfPossible);
p.makeBondsGeneric = pt.get("makeBondsGeneric", p.makeBondsGeneric);
p.makeAtomsGeneric = pt.get("makeAtomsGeneric", p.makeAtomsGeneric);
p.adjustHeavyDegree = pt.get("adjustHeavyDegree", p.adjustHeavyDegree);
p.adjustRingChain = pt.get("adjustRingChain", p.adjustRingChain);
p.useStereoCareForBonds =
pt.get("useStereoCareForBonds", p.useStereoCareForBonds);
p.adjustConjugatedFiveRings =
pt.get("adjustConjugatedFiveRings", p.adjustConjugatedFiveRings);
p.setMDLFiveRingAromaticity =
pt.get("setMDLFiveRingAromaticity", p.setMDLFiveRingAromaticity);
p.adjustSingleBondsToDegreeOneNeighbors =
pt.get("adjustSingleBondsToDegreeOneNeighbors",
p.adjustSingleBondsToDegreeOneNeighbors);
p.adjustSingleBondsBetweenAromaticAtoms =
pt.get("adjustSingleBondsBetweenAromaticAtoms",
p.adjustSingleBondsBetweenAromaticAtoms);
std::string which;
which = boost::to_upper_copy<std::string>(pt.get("adjustDegreeFlags", ""));
if (!which.empty()) {
p.adjustDegreeFlags = parseWhichString(which);
}
which =
boost::to_upper_copy<std::string>(pt.get("adjustHeavyDegreeFlags", ""));
if (!which.empty()) {
p.adjustHeavyDegreeFlags = parseWhichString(which);
}
which = boost::to_upper_copy<std::string>(pt.get("adjustRingCountFlags", ""));
if (!which.empty()) {
p.adjustRingCountFlags = parseWhichString(which);
}
which =
boost::to_upper_copy<std::string>(pt.get("makeBondsGenericFlags", ""));
if (!which.empty()) {
p.makeBondsGenericFlags = parseWhichString(which);
}
which =
boost::to_upper_copy<std::string>(pt.get("makeAtomsGenericFlags", ""));
if (!which.empty()) {
p.makeAtomsGenericFlags = parseWhichString(which);
}
which = boost::to_upper_copy<std::string>(pt.get("adjustRingChainFlags", ""));
if (!which.empty()) {
p.adjustRingCountFlags = parseWhichString(which);
}
} // namespace MolOps
ROMol *adjustQueryProperties(const ROMol &mol,
const AdjustQueryParameters *params) {
auto *res = new RWMol(mol);
try {
adjustQueryProperties(*res, params);
} catch (MolSanitizeException &se) {
delete res;
throw se;
}
return static_cast<ROMol *>(res);
}
void adjustQueryProperties(RWMol &mol, const AdjustQueryParameters *inParams) {
AdjustQueryParameters params;
if (inParams) {
params = *inParams;
}
const RingInfo *ringInfo = mol.getRingInfo();
if (params.aromatizeIfPossible) {
unsigned int failed;
sanitizeMol(mol, failed, SANITIZE_SYMMRINGS | SANITIZE_SETAROMATICITY);
} else {
if (!ringInfo->isInitialized()) {
MolOps::symmetrizeSSSR(mol);
}
}
if (params.makeAtomsGeneric) {
for (unsigned int i = 0; i < mol.getNumAtoms(); ++i) {
if (!((params.makeAtomsGenericFlags & ADJUST_IGNORECHAINS) &&
!ringInfo->numAtomRings(i)) &&
!((params.makeAtomsGenericFlags & ADJUST_IGNORERINGS) &&
ringInfo->numAtomRings(i)) &&
!((params.adjustDegreeFlags & ADJUST_IGNOREMAPPED) &&
isMapped(mol.getAtomWithIdx(i)))) {
auto *qa = new QueryAtom();
qa->setQuery(makeAtomNullQuery());
const bool updateLabel = false;
const bool preserveProps = true;
mol.replaceAtom(i, qa, updateLabel, preserveProps);
delete qa;
}
}
} // end of makeAtomsGeneric
if (params.makeBondsGeneric) {
for (unsigned int i = 0; i < mol.getNumBonds(); ++i) {
if (!((params.makeBondsGenericFlags & ADJUST_IGNORECHAINS) &&
!ringInfo->numBondRings(i)) &&
!((params.makeBondsGenericFlags & ADJUST_IGNORERINGS) &&
ringInfo->numBondRings(i))) {
auto *qb = new QueryBond();
qb->setQuery(makeBondNullQuery());
const bool preserveProps = true;
mol.replaceBond(i, qb, preserveProps);
delete qb;
}
}
} // end of makeBondsGeneric
for (unsigned int i = 0; i < mol.getNumAtoms(); ++i) {
Atom *at = mol.getAtomWithIdx(i);
// pull properties we need from the atom here, once we
// create a query atom they may no longer be valid.
unsigned int nRings = ringInfo->numAtomRings(i);
int atomicNum = at->getAtomicNum();
if (params.makeDummiesQueries && atomicNum == 0 && !at->hasQuery() &&
!at->getIsotope()) {
auto *qa = new QueryAtom();
qa->setQuery(makeAtomNullQuery());
const bool updateLabel = false;
const bool preserveProps = true;
mol.replaceAtom(i, qa, updateLabel, preserveProps);
delete qa;
at = mol.getAtomWithIdx(i);
} // end of makeDummiesQueries
if (params.adjustDegree &&
!((params.adjustDegreeFlags & ADJUST_IGNORECHAINS) && !nRings) &&
!((params.adjustDegreeFlags & ADJUST_IGNORERINGS) && nRings) &&
!((params.adjustDegreeFlags & ADJUST_IGNOREDUMMIES) && !atomicNum) &&
!((params.adjustDegreeFlags & ADJUST_IGNORENONDUMMIES) && atomicNum) &&
!((params.adjustDegreeFlags & ADJUST_IGNOREMAPPED) && isMapped(at))) {
QueryAtom *qa;
if (!at->hasQuery()) {
qa = new QueryAtom(*at);
const bool updateLabel = false;
const bool preserveProps = true;
mol.replaceAtom(i, qa, updateLabel, preserveProps);
delete qa;
qa = static_cast<QueryAtom *>(mol.getAtomWithIdx(i));
at = static_cast<Atom *>(qa);
} else {
qa = static_cast<QueryAtom *>(at);
}
qa->expandQuery(makeAtomExplicitDegreeQuery(qa->getDegree()));
} // end of adjust degree
if (params.adjustHeavyDegree &&
!((params.adjustHeavyDegreeFlags & ADJUST_IGNORECHAINS) && !nRings) &&
!((params.adjustHeavyDegreeFlags & ADJUST_IGNORERINGS) && nRings) &&
!((params.adjustHeavyDegreeFlags & ADJUST_IGNOREDUMMIES) &&
!atomicNum) &&
!((params.adjustHeavyDegreeFlags & ADJUST_IGNORENONDUMMIES) &&
atomicNum) &&
!((params.adjustHeavyDegreeFlags & ADJUST_IGNOREMAPPED) &&
isMapped(at))) {
QueryAtom *qa;
if (!at->hasQuery()) {
qa = new QueryAtom(*at);
const bool updateLabel = false;
const bool preserveProps = true;
mol.replaceAtom(i, qa, updateLabel, preserveProps);
delete qa;
qa = static_cast<QueryAtom *>(mol.getAtomWithIdx(i));
at = static_cast<Atom *>(qa);
} else {
qa = static_cast<QueryAtom *>(at);
}
qa->expandQuery(makeAtomHeavyAtomDegreeQuery(qa->getTotalDegree() -
qa->getTotalNumHs(true)));
} // end of adjust heavy degree
if (params.adjustRingCount &&
!((params.adjustRingCountFlags & ADJUST_IGNORECHAINS) && !nRings) &&
!((params.adjustRingCountFlags & ADJUST_IGNORERINGS) && nRings) &&
!((params.adjustRingCountFlags & ADJUST_IGNOREDUMMIES) && !atomicNum) &&
!((params.adjustRingCountFlags & ADJUST_IGNORENONDUMMIES) &&
atomicNum) &&
!((params.adjustRingCountFlags & ADJUST_IGNOREMAPPED) &&
isMapped(at))) {
QueryAtom *qa;
if (!at->hasQuery()) {
qa = new QueryAtom(*at);
const bool updateLabel = false;
const bool preserveProps = true;
mol.replaceAtom(i, qa, updateLabel, preserveProps);
delete qa;
qa = static_cast<QueryAtom *>(mol.getAtomWithIdx(i));
at = static_cast<Atom *>(qa);
} else {
qa = static_cast<QueryAtom *>(at);
}
qa->expandQuery(makeAtomInNRingsQuery(nRings));
} // end of adjust ring count
if (params.adjustRingChain &&
!((params.adjustRingChainFlags & ADJUST_IGNORECHAINS) && !nRings) &&
!((params.adjustRingChainFlags & ADJUST_IGNORERINGS) && nRings) &&
!((params.adjustRingChainFlags & ADJUST_IGNOREDUMMIES) && !atomicNum) &&
!((params.adjustRingChainFlags & ADJUST_IGNORENONDUMMIES) &&
atomicNum) &&
!((params.adjustRingChainFlags & ADJUST_IGNOREMAPPED) &&
isMapped(at))) {
QueryAtom *qa;
if (!at->hasQuery()) {
qa = new QueryAtom(*at);
const bool updateLabel = false;
const bool preserveProps = true;
mol.replaceAtom(i, qa, updateLabel, preserveProps);
delete qa;
qa = static_cast<QueryAtom *>(mol.getAtomWithIdx(i));
at = static_cast<Atom *>(qa);
} else {
qa = static_cast<QueryAtom *>(at);
}
ATOM_EQUALS_QUERY *nq = makeAtomInRingQuery();
if (!nRings) {
nq->setNegation(true);
}
qa->expandQuery(nq);
} // end of adjust ring chain
} // end of loop over atoms
if (params.useStereoCareForBonds) {
for (auto bnd : mol.bonds()) {
if (bnd->getBondType() == Bond::BondType::DOUBLE) {
if (bnd->getStereo() > Bond::BondStereo::STEREOANY) {
bool preserve = false;
int val = 0;
// is stereoCare set on the bond or both atoms?
if (bnd->getPropIfPresent(common_properties::molStereoCare, val) &&
val) {
preserve = true;
}
if (!preserve) {
bnd->setStereo(Bond::BondStereo::STEREONONE);
}
}
}
}
}
if (params.setMDLFiveRingAromaticity) {
setMDLAromaticity(mol);
}
if (params.adjustConjugatedFiveRings) {
adjustConjugatedFiveRings(mol);
}
if (params.adjustSingleBondsToDegreeOneNeighbors ||
params.adjustSingleBondsBetweenAromaticAtoms) {
adjustSingleBondsFromAromaticAtoms(
mol, params.adjustSingleBondsToDegreeOneNeighbors,
params.adjustSingleBondsBetweenAromaticAtoms);
}
}
} // namespace MolOps
} // namespace RDKit
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