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//
// Copyright (c) 2024 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 <catch2/catch_all.hpp>
#include <GraphMol/RDKitBase.h>
#include <GraphMol/MolTransforms/MolTransforms.h>
#include <GraphMol/FileParsers/FileParsers.h>
#include <algorithm>
#include <regex>
using namespace RDKit;
using std::unique_ptr;
TEST_CASE("chirality flip in canonicalizeMolConformer") {
SECTION("first discovery") {
auto m1 = R"CTAB(
RDKit 3D
0 0 0 0 0 0 0 0 0 0999 V3000
M V30 BEGIN CTAB
M V30 COUNTS 11 10 0 0 0
M V30 BEGIN ATOM
M V30 1 C -1.533948 2.465972 -1.220733 0
M V30 2 C -1.361222 1.165424 -1.939720 0 CFG=2
M V30 3 C -2.694145 0.606596 -2.153754 0
M V30 4 N -3.766061 0.178135 -2.319155 0
M V30 5 C -0.566772 0.289201 -1.072783 0
M V30 6 C 0.084234 -0.420637 -0.345400 0
M V30 7 C 0.867082 -1.237691 0.508367 0
M V30 8 C 1.549171 -1.919699 1.232613 0
M V30 9 C 2.339643 -2.731169 2.106347 0
M V30 10 C 2.993349 -3.411935 2.854815 0
M V30 11 O 3.747921 -4.178375 3.716269 0
M V30 END ATOM
M V30 BEGIN BOND
M V30 1 1 2 1 CFG=1
M V30 2 1 2 3
M V30 3 3 3 4
M V30 4 1 2 5
M V30 5 3 5 6
M V30 6 1 6 7
M V30 7 3 7 8
M V30 8 1 8 9
M V30 9 3 9 10
M V30 10 1 10 11
M V30 END BOND
M V30 END CTAB
M END)CTAB"_ctab;
REQUIRE(m1);
auto m2 = R"CTAB(
RDKit 3D
0 0 0 0 0 0 0 0 0 0999 V3000
M V30 BEGIN CTAB
M V30 COUNTS 11 10 0 0 0
M V30 BEGIN ATOM
M V30 1 C -3.278200 0.712725 -0.066592 0
M V30 2 C -2.682025 -0.648154 -0.271665 0 CFG=1
M V30 3 C -2.915612 -1.059871 -1.656844 0
M V30 4 N -3.080403 -1.390524 -2.739848 0
M V30 5 C -1.232937 -0.539032 -0.023304 0
M V30 6 C -0.029030 -0.463778 0.167869 0
M V30 7 C 1.366183 -0.398546 0.377840 0
M V30 8 C 2.562372 -0.361417 0.548269 0
M V30 9 C 3.973502 -0.322846 0.772691 0
M V30 10 C 5.164230 -0.269523 0.960648 0
M V30 11 O 6.516239 -0.218493 1.152837 0
M V30 END ATOM
M V30 BEGIN BOND
M V30 1 1 2 1 CFG=3
M V30 2 1 2 3
M V30 3 3 3 4
M V30 4 1 2 5
M V30 5 3 5 6
M V30 6 1 6 7
M V30 7 3 7 8
M V30 8 1 8 9
M V30 9 3 9 10
M V30 10 1 10 11
M V30 END BOND
M V30 END CTAB
M END)CTAB"_ctab;
REQUIRE(m2);
auto m1_cp = ROMol(*m1);
auto m2_cp = ROMol(*m2);
MolTransforms::canonicalizeConformer(m1_cp.getConformer());
MolTransforms::canonicalizeConformer(m2_cp.getConformer());
MolOps::assignChiralTypesFrom3D(m1_cp);
MolOps::assignChiralTypesFrom3D(m2_cp);
CHECK(m1_cp.getAtomWithIdx(1)->getChiralTag() ==
m1->getAtomWithIdx(1)->getChiralTag());
CHECK(m2_cp.getAtomWithIdx(1)->getChiralTag() ==
m2->getAtomWithIdx(1)->getChiralTag());
}
}
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