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860 lines
54 KiB
C++
860 lines
54 KiB
C++
//
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// Copyright (C) 2026 David Cosgrove and other RDKit contributors
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//
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// @@ All Rights Reserved @@
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// This file is part of the RDKit.
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// The contents are covered by the terms of the BSD license
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// which is included in the file license.txt, found at the root
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// of the RDKit source tree.
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//
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// Original author: David Cosgrove (CozChemIx Limited)
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//
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// Tests for the Roshambo2-based shape alignment code.
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#include <chrono>
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#include <random>
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#include <algorithm>
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#include <execution>
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#include <catch2/catch_test_macros.hpp>
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#include <catch2/matchers/catch_matchers_floating_point.hpp>
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#include <GraphMol/MolOps.h>
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#include <GraphMol/FileParsers/MolWriters.h>
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#include <GraphMol/FileParsers/MolSupplier.h>
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#include <GraphMol/GaussianShape/GaussianShape.h>
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#include <GraphMol/GaussianShape/ShapeInput.h>
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#include <GraphMol/MolTransforms/MolTransforms.h>
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#include <GraphMol/SmilesParse/SmilesWrite.h>
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using namespace RDKit;
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bool checkMolsHaveRoughlySameCoords(const ROMol &m1, const ROMol &m2,
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double margin = 0.005) {
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for (unsigned int i = 0; i < m1.getNumAtoms(); ++i) {
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auto pos1 = m1.getConformer().getAtomPos(i);
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auto pos2 = m2.getConformer().getAtomPos(i);
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if ((pos1 - pos2).length() > margin) {
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// So the error is printed in a relevant place.
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std::cout << i << " : " << m1.getAtomWithIdx(i)->getAtomicNum()
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<< " :: " << (pos1 - pos2).length() << std::endl;
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CHECK_THAT((pos1 - pos2).length(),
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Catch::Matchers::WithinAbs(0.0, margin));
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return false;
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}
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}
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return true;
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}
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TEST_CASE("basic alignment") {
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std::string dirName = getenv("RDBASE");
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dirName += "/External/pubchem_shape/test_data";
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auto suppl = v2::FileParsers::SDMolSupplier(dirName + "/test1.sdf");
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auto refT = suppl[0];
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auto ref = v2::SmilesParse::MolFromSmiles(MolToCXSmiles(*refT));
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REQUIRE(ref);
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auto probeT = suppl[1];
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auto probe = v2::SmilesParse::MolFromSmiles(MolToCXSmiles(*probeT));
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REQUIRE(probe);
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GaussianShape::ShapeOverlayOptions overlayOpts;
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overlayOpts.optimMode = GaussianShape::OptimMode::SHAPE_PLUS_COLOR_SCORE;
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overlayOpts.startMode = GaussianShape::StartMode::ROTATE_180;
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overlayOpts.nSteps = 50;
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GaussianShape::ShapeInputOptions shapeOpts;
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SECTION("setup") {
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auto refShape = GaussianShape::ShapeInput(*ref, -1, shapeOpts);
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CHECK_THAT(refShape.getShapeVolume(),
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Catch::Matchers::WithinAbs(591.057, 0.005));
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CHECK_THAT(refShape.getColorVolume(),
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Catch::Matchers::WithinAbs(31.935, 0.005));
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auto probeShape = GaussianShape::ShapeInput(*probe, -1, shapeOpts);
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CHECK_THAT(probeShape.getShapeVolume(),
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Catch::Matchers::WithinAbs(751.013, 0.005));
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CHECK_THAT(probeShape.getColorVolume(),
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Catch::Matchers::WithinAbs(42.530, 0.005));
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}
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SECTION("shape only") {
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ROMol cp(*probe);
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overlayOpts.optimMode = GaussianShape::OptimMode::SHAPE_ONLY;
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overlayOpts.startMode = GaussianShape::StartMode::ROTATE_180;
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GaussianShape::ShapeInputOptions tShapeOpts;
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tShapeOpts.useColors = false;
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const auto scores = GaussianShape::AlignMolecule(
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*ref, cp, tShapeOpts, tShapeOpts, nullptr, overlayOpts);
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CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.760, 0.005));
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CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.760, 0.005));
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CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.0, 0.005));
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// Check that a re-score gives the same answer.
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auto rescores = GaussianShape::ScoreMolecule(*ref, cp, shapeOpts, shapeOpts,
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overlayOpts);
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CHECK_THAT(rescores[0], Catch::Matchers::WithinAbs(scores[0], 0.005));
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CHECK_THAT(rescores[1], Catch::Matchers::WithinAbs(scores[1], 0.005));
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CHECK_THAT(rescores[2], Catch::Matchers::WithinAbs(scores[2], 0.005));
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}
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SECTION("shape plus color score") {
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overlayOpts.optimMode = GaussianShape::OptimMode::SHAPE_PLUS_COLOR_SCORE;
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overlayOpts.startMode = GaussianShape::StartMode::ROTATE_180;
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ROMol cp(*probe);
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const auto scores = GaussianShape::AlignMolecule(
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*ref, cp, shapeOpts, shapeOpts, nullptr, overlayOpts);
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CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.494, 0.005));
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CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.760, 0.005));
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CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.236, 0.005));
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// Check that a re-score gives the same answer.
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const auto rescores = GaussianShape::ScoreMolecule(*ref, cp, shapeOpts,
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shapeOpts, overlayOpts);
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CHECK_THAT(rescores[0], Catch::Matchers::WithinAbs(scores[0], 0.005));
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CHECK_THAT(rescores[1], Catch::Matchers::WithinAbs(scores[1], 0.005));
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CHECK_THAT(rescores[2], Catch::Matchers::WithinAbs(scores[2], 0.005));
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}
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SECTION("shape and color") {
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overlayOpts.optimMode = GaussianShape::OptimMode::SHAPE_PLUS_COLOR;
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overlayOpts.startMode = GaussianShape::StartMode::ROTATE_180;
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ROMol cp(*probe);
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const auto scores = GaussianShape::AlignMolecule(
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*ref, cp, shapeOpts, shapeOpts, nullptr, overlayOpts);
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CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.477, 0.005));
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CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.747, 0.005));
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CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.207, 0.005));
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const auto rescores = GaussianShape::ScoreMolecule(*ref, cp, shapeOpts,
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shapeOpts, overlayOpts);
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CHECK_THAT(rescores[0], Catch::Matchers::WithinAbs(scores[0], 0.005));
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CHECK_THAT(rescores[1], Catch::Matchers::WithinAbs(scores[1], 0.005));
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CHECK_THAT(rescores[2], Catch::Matchers::WithinAbs(scores[2], 0.005));
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}
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SECTION("collect transform") {
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overlayOpts.optimMode = GaussianShape::OptimMode::SHAPE_PLUS_COLOR_SCORE;
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overlayOpts.startMode = GaussianShape::StartMode::ROTATE_180;
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ROMol cp(*probe);
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RDGeom::Transform3D xform;
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const auto scores = GaussianShape::AlignMolecule(
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*ref, cp, shapeOpts, shapeOpts, &xform, overlayOpts);
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CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.494, 0.005));
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CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.760, 0.005));
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CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.236, 0.005));
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// Check a few values from the transform, just to be sure
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CHECK_THAT(xform.getValUnchecked(0, 0),
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Catch::Matchers::WithinAbs(-0.886, 0.005));
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CHECK_THAT(xform.getValUnchecked(1, 1),
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Catch::Matchers::WithinAbs(-0.828, 0.005));
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CHECK_THAT(xform.getValUnchecked(2, 2),
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Catch::Matchers::WithinAbs(0.816, 0.005));
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CHECK_THAT(xform.getValUnchecked(3, 3),
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Catch::Matchers::WithinAbs(1.0, 0.005));
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}
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SECTION("shape plus color score a la pubchem") {
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overlayOpts.optimMode = GaussianShape::OptimMode::SHAPE_PLUS_COLOR_SCORE;
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overlayOpts.startMode = GaussianShape::StartMode::A_LA_PUBCHEM;
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GaussianShape::ShapeInputOptions shapeOpts2;
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for (const auto acr : std::vector{true, false}) {
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shapeOpts2.allCarbonRadii = acr;
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ROMol cp(*probe);
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const auto scores = GaussianShape::AlignMolecule(
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*ref, cp, shapeOpts2, shapeOpts2, nullptr, overlayOpts);
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if (acr) {
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CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.498, 0.005));
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CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.758, 0.005));
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CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.237, 0.005));
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} else {
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CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.503, 0.005));
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CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.761, 0.005));
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CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.233, 0.005));
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}
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// Check that a re-score gives the same answer.
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const auto rescores = GaussianShape::ScoreMolecule(
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*ref, cp, shapeOpts2, shapeOpts2, overlayOpts);
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CHECK_THAT(rescores[0], Catch::Matchers::WithinAbs(scores[0], 0.005));
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CHECK_THAT(rescores[1], Catch::Matchers::WithinAbs(scores[1], 0.005));
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CHECK_THAT(rescores[2], Catch::Matchers::WithinAbs(scores[2], 0.005));
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}
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}
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}
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TEST_CASE("bulk") {
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std::string dirName = getenv("RDBASE");
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dirName += "/External/pubchem_shape/test_data";
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auto suppl = v2::FileParsers::SDMolSupplier(dirName + "/bulk.pubchem.sdf");
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auto ref = suppl[0];
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REQUIRE(ref);
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std::string testout = dirName + "/bulk.pubchem_out.sdf";
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auto writer = SDWriter(testout);
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writer.write(*ref);
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GaussianShape::ShapeOverlayOptions overlayOpts;
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overlayOpts.optimMode = GaussianShape::OptimMode::SHAPE_PLUS_COLOR_SCORE;
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overlayOpts.startMode = GaussianShape::StartMode::A_LA_PUBCHEM;
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GaussianShape::ShapeInputOptions shapeOpts;
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for (auto i = 1u; i < suppl.length(); ++i) {
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auto probe = suppl[1];
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REQUIRE(probe);
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auto scores = GaussianShape::AlignMolecule(*ref, *probe, shapeOpts,
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shapeOpts, nullptr, overlayOpts);
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CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.575, 0.005));
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CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.818, 0.005));
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CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.332, 0.005));
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const auto rescores = GaussianShape::ScoreMolecule(*ref, *probe);
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CHECK_THAT(rescores[0], Catch::Matchers::WithinAbs(scores[0], 0.005));
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CHECK_THAT(rescores[1], Catch::Matchers::WithinAbs(scores[1], 0.005));
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CHECK_THAT(rescores[2], Catch::Matchers::WithinAbs(scores[2], 0.005));
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writer.write(*probe);
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break;
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}
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writer.close();
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}
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TEST_CASE("shape alignment") {
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std::string dirName = getenv("RDBASE");
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dirName += "/External/pubchem_shape/test_data";
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auto suppl = v2::FileParsers::SDMolSupplier(dirName + "/test1.sdf");
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auto ref = suppl[0];
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REQUIRE(ref);
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auto probe = suppl[1];
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REQUIRE(probe);
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auto refShape = GaussianShape::ShapeInput(*ref, -1);
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auto probeShape = GaussianShape::ShapeInput(*probe, -1);
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const auto ovProbe =
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"FC1(F)C[C@H](C(O)=O)N(Cc2ocnc2)C1 |(-13.7799,-5.76066,4.42449;-13.5271,-6.62223,3.41219;-12.4707,-7.37583,3.76844;-13.2679,-5.8659,2.12715;-14.6435,-5.78022,1.46335;-15.139,-4.37081,1.41003;-14.7786,-3.78046,0.244433;-15.7838,-3.81972,2.28974;-15.5606,-6.52351,2.33643;-16.628,-7.19488,1.60806;-17.7234,-6.24049,1.21312;-18.3383,-5.54964,2.21298;-19.2578,-4.78996,1.55674;-19.2808,-4.93485,0.251035;-18.298,-5.86438,0.0244256;-14.7486,-7.4588,3.11797),wU:4.4|"_smiles;
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RDGeom::Transform3D xform;
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auto scores = GaussianShape::AlignShape(refShape, probeShape, &xform);
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CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.498, 0.005));
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CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.760, 0.005));
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CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.235, 0.005));
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// This effectively checks that xform is correct.
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auto rescores = GaussianShape::ScoreShape(refShape, probeShape);
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CHECK_THAT(rescores[0], Catch::Matchers::WithinAbs(scores[0], 0.001));
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CHECK_THAT(rescores[1], Catch::Matchers::WithinAbs(scores[1], 0.001));
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CHECK_THAT(rescores[2], Catch::Matchers::WithinAbs(scores[2], 0.001));
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SmilesWriteParams params;
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params.canonical = false;
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// The input structure being from an SDF doesn't have the atoms in an order
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// that will make a SMILES string so bounce it through one for comparison.
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auto probeCp1 = v2::SmilesParse::MolFromSmiles(MolToCXSmiles(*probe, params));
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MolTransforms::transformConformer(probeCp1->getConformer(), xform);
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CHECK(checkMolsHaveRoughlySameCoords(*ovProbe, *probeCp1));
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// And pre-normalizing the shapes
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refShape.normalizeCoords();
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probeShape.normalizeCoords();
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RDGeom::Transform3D xform1;
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auto scores1 = GaussianShape::AlignShape(refShape, probeShape, &xform1);
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CHECK_THAT(scores1[0], Catch::Matchers::WithinAbs(0.498, 0.005));
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CHECK_THAT(scores1[1], Catch::Matchers::WithinAbs(0.760, 0.005));
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CHECK_THAT(scores1[2], Catch::Matchers::WithinAbs(0.235, 0.005));
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}
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TEST_CASE("Overlay onto shape bug (Github8462)") {
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auto m1 =
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R"(c1ccc(-c2ccccc2)cc1 |(-3.26053,-0.0841607,-0.741909;-2.93383,0.123873,0.593407;-1.60713,0.377277,0.917966;-0.644758,0.654885,-0.0378428;0.743308,0.219134,0.168663;1.82376,1.0395,-0.0112769;3.01462,0.695405,0.613858;3.18783,-0.589771,1.09649;2.15761,-1.50458,1.01949;0.988307,-1.1313,0.385783;-1.1048,0.797771,-1.34022;-2.39754,0.435801,-1.69921)|)"_smiles;
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REQUIRE(m1);
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ROMol m2(*m1);
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for (auto a : m2.atoms()) {
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auto &pos = m2.getConformer().getAtomPos(a->getIdx());
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pos.x += 3.0;
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pos.y += 2.0;
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}
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ROMol m3(m2);
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auto scores = GaussianShape::AlignMolecule(*m1, m2);
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CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(1.0, 0.005));
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CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(1.0, 0.005));
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CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(1.0, 0.005));
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CHECK(checkMolsHaveRoughlySameCoords(*m1, m2, 0.005));
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// Create the shape without normalization to mimic an arbitrary shape.
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auto s1 = GaussianShape::ShapeInput(*m1, -1);
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auto scores1 = AlignMolecule(s1, m3);
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CHECK_THAT(scores1[0], Catch::Matchers::WithinAbs(1.0, 0.005));
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CHECK_THAT(scores1[1], Catch::Matchers::WithinAbs(1.0, 0.005));
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CHECK_THAT(scores1[2], Catch::Matchers::WithinAbs(1.0, 0.005));
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for (unsigned int i = 0; i < m3.getNumAtoms(); ++i) {
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RDGeom::Point3D pos1(s1.getCoords()[4 * i], s1.getCoords()[4 * i + 1],
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s1.getCoords()[4 * i + 2]);
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auto pos2 = m3.getConformer().getAtomPos(i);
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CHECK_THAT((pos1 - pos2).length(), Catch::Matchers::WithinAbs(0.0, 0.01));
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}
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}
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TEST_CASE("handling molecules with Hs") {
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std::string dirName = getenv("RDBASE");
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dirName += "/External/pubchem_shape/test_data";
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v2::FileParsers::MolFileParserParams params;
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params.removeHs = false;
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auto suppl =
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v2::FileParsers::SDMolSupplier(dirName + "/align_with_hs.sdf", params);
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auto ref = suppl[0];
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REQUIRE(ref);
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auto probe = suppl[1];
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REQUIRE(probe);
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SECTION("basics") {
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RWMol cp(*probe);
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RDGeom::Transform3D xform;
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auto scores = GaussianShape::AlignMolecule(*ref, cp);
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CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.736, 0.005));
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CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.834, 0.005));
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CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.635, 0.005));
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for (auto i = 0u; i < cp.getNumAtoms(); ++i) {
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// the failure mode here was that Hs had HUGE coordinates
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auto pos = cp.getConformer().getAtomPos(i);
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CHECK((pos.x > -10 && pos.x < 10));
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}
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// Check the rescore
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auto rescores = GaussianShape::ScoreMolecule(*ref, cp);
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CHECK_THAT(rescores[0], Catch::Matchers::WithinAbs(scores[0], 0.005));
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CHECK_THAT(rescores[1], Catch::Matchers::WithinAbs(scores[1], 0.005));
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CHECK_THAT(rescores[2], Catch::Matchers::WithinAbs(scores[2], 0.005));
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}
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}
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TEST_CASE("Github #8096") {
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SECTION("as reported") {
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auto m1 =
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R"([H]c1c([H])c([H])c([2H])c([H])c1[H] |(1.55967,1.91617,0.0546381;0.885536,1.07172,0.030849;1.38172,-0.23747,0.0274262;2.44539,-0.439501,0.0483424;0.470206,-1.27516,-0.00361916;0.856925,-2.30002,-0.00633525;-0.896665,-1.07227,-0.0310991;-1.60071,-1.87642,-0.0551085;-1.36315,0.22877,-0.0271173;-2.43593,0.379132,-0.0487835;-0.479018,1.29083,0.00359778;-0.823965,2.31421,0.00720933)|)"_smiles;
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REQUIRE(m1);
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auto m2 =
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R"([H]c1c([H])c([H])c([H])c([H])c1[H] |(-2.06264,-0.844763,-0.0261403;-1.04035,-0.481453,-0.0114878;-0.00743655,-1.41861,-0.0137121;-0.215455,-2.47997,-0.0295909;1.29853,-0.949412,0.00507497;2.12524,-1.65277,0.00390664;1.58501,0.395878,0.0254188;2.61997,0.704365,0.0394811;0.550242,1.31385,0.0273741;0.783172,2.37039,0.0434262;-0.763786,0.88847,0.00908113;-1.60557,1.58532,0.0100194)|)"_smiles;
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REQUIRE(m2);
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auto scores = GaussianShape::AlignMolecule(*m1, *m2);
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CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(1.0, 0.005));
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CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(1.0, 0.005));
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CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(1.0, 0.005));
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}
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}
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TEST_CASE("Hs not properly transformed when hcount = feature count") {
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std::string dirName = getenv("RDBASE");
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dirName += "/External/pubchem_shape/test_data";
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SECTION("as reported") {
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v2::FileParsers::MolFileParserParams ps;
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ps.removeHs = false;
|
|
auto mol1 =
|
|
v2::FileParsers::MolFromMolFile(dirName + "/hcount_ex1_1.mol", ps);
|
|
REQUIRE(mol1);
|
|
auto mol2 =
|
|
v2::FileParsers::MolFromMolFile(dirName + "/hcount_ex1_2.mol", ps);
|
|
REQUIRE(mol2);
|
|
{
|
|
RWMol cp(*mol2);
|
|
auto scores = GaussianShape::AlignMolecule(*mol1, cp);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.744, 0.005));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.918, 0.005));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.570, 0.005));
|
|
// the bug led to H atoms in stupid positions, so we can detect it by just
|
|
// looking at bond lengths to Hs:
|
|
for (auto i = cp.getNumHeavyAtoms(); i < cp.getNumAtoms(); ++i) {
|
|
INFO("checking atom " << i);
|
|
auto at = cp.getAtomWithIdx(i);
|
|
for (auto nbr : cp.atomNeighbors(at)) {
|
|
auto dist = (cp.getConformer().getAtomPos(i) -
|
|
cp.getConformer().getAtomPos(nbr->getIdx()))
|
|
.length();
|
|
CHECK(dist < 1.2); // should be a bond to H
|
|
}
|
|
}
|
|
}
|
|
}
|
|
}
|
|
|
|
TEST_CASE("Score No Overlay") {
|
|
// These are 2 ligands used by Andy Grant and Co in their original paper
|
|
// https://onlinelibrary.wiley.com/doi/10.1002/(SICI)1096-987X(19961115)17:14%3C1653::AID-JCC7%3E3.0.CO;2-K
|
|
// Ligands as extracted from PDB, with a bit of munging to get them as
|
|
// SMILES strings (downloaded the Ideal ligand structures from RCSB
|
|
// as SDFs and transferred the corresponding atom coords from 3tmn and 1tmn).
|
|
auto pdb_trp_3tmn =
|
|
R"(N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2 |(37.935,40.394,-3.825;39.119,39.593,-4.13;38.758,38.486,-5.101;37.526,38.337,-5.395;39.716,37.852,-5.605;39.883,39.108,-2.906;39.086,38.098,-2.209;38.093,38.363,-1.34;37.565,37.179,-0.881;38.201,36.136,-1.471;39.193,36.684,-2.308;40.015,35.812,-3.036;39.846,34.441,-2.913;38.844,33.933,-2.075;38.015,34.752,-1.333),wU:1.0|)"_smiles;
|
|
REQUIRE(pdb_trp_3tmn);
|
|
auto pdb_0zn_1tmn =
|
|
R"([C@H](CCc1ccccc1)(C(=O)O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2)CC(C)C |(35.672,41.482,-5.722;34.516,40.842,-6.512;34.843,39.355,-6.7;33.819,38.475,-7.45;33.825,38.414,-8.838;32.951,37.553,-9.53;32.064,36.747,-8.81;32.096,36.799,-7.402;32.985,37.656,-6.73;35.934,42.778,-6.452;36.833,42.858,-7.316;35.175,43.735,-6.275;35.516,41.561,-4.218;36.707,42.096,-3.513;38.055,41.449,-3.859;39.11,42.138,-3.959;37.975,40.129,-3.983;39.134,39.277,-4.298;38.825,38.04,-5.133;37.649,37.934,-5.605;39.788,37.369,-5.652;39.985,38.945,-3.037;39.221,37.953,-2.164;37.934,37.961,-1.823;37.579,36.695,-1.314;38.63,35.975,-1.286;39.736,36.771,-1.642;41.052,36.341,-1.48;41.213,35.042,-0.964;40.095,34.215,-0.69;38.765,34.665,-0.855;36.506,41.966,-2.002;37.6,42.757,-1.31;37.546,44.225,-1.728;37.408,42.58,0.19),wD:0.0,wU:17.21,13.33|)"_smiles;
|
|
REQUIRE(pdb_0zn_1tmn);
|
|
GaussianShape::ShapeInputOptions shapeOpts;
|
|
{
|
|
auto scores = ScoreMolecule(*pdb_trp_3tmn, *pdb_trp_3tmn, shapeOpts);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(1.0, 0.001));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(1.0, 0.001));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(1.0, 0.001));
|
|
}
|
|
{
|
|
auto pdb_trp_3tmn_cp =
|
|
R"(N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2 |(37.935,40.394,-3.825;39.119,39.593,-4.13;38.758,38.486,-5.101;37.526,38.337,-5.395;39.716,37.852,-5.605;39.883,39.108,-2.906;39.086,38.098,-2.209;38.093,38.363,-1.34;37.565,37.179,-0.881;38.201,36.136,-1.471;39.193,36.684,-2.308;40.015,35.812,-3.036;39.846,34.441,-2.913;38.844,33.933,-2.075;38.015,34.752,-1.333),wU:1.0|)"_smiles;
|
|
RDGeom::Point3D trans{100.0, 100.0, 100.0};
|
|
RDGeom::Transform3D transform_3d;
|
|
transform_3d.SetTranslation(trans);
|
|
MolTransforms::transformConformer(pdb_trp_3tmn_cp->getConformer(),
|
|
transform_3d);
|
|
|
|
auto scores = ScoreMolecule(*pdb_trp_3tmn, *pdb_trp_3tmn_cp, shapeOpts);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.0, 0.001));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.0, 0.001));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.0, 0.001));
|
|
}
|
|
{
|
|
auto scores = ScoreMolecule(*pdb_0zn_1tmn, *pdb_0zn_1tmn, shapeOpts);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(1.0, 0.001));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(1.0, 0.001));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(1.0, 0.001));
|
|
}
|
|
{
|
|
auto scores = ScoreMolecule(*pdb_trp_3tmn, *pdb_0zn_1tmn, shapeOpts);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.307, 0.005));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.349, 0.005));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.265, 0.005));
|
|
}
|
|
{
|
|
auto shape = GaussianShape::ShapeInput(*pdb_trp_3tmn, -1, shapeOpts);
|
|
auto scores = ScoreMolecule(shape, *pdb_0zn_1tmn, shapeOpts);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.307, 0.005));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.349, 0.005));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.265, 0.005));
|
|
}
|
|
{
|
|
auto shape1 = GaussianShape::ShapeInput(*pdb_trp_3tmn, -1, shapeOpts);
|
|
auto shape2 = GaussianShape::ShapeInput(*pdb_0zn_1tmn, -1, shapeOpts);
|
|
auto scores = GaussianShape::ScoreShape(shape1, shape2);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.307, 0.005));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.349, 0.005));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.265, 0.005));
|
|
}
|
|
}
|
|
|
|
TEST_CASE("Iressa onto Tagrisso") {
|
|
// Conformations from PubChem produced by Omega. Iressa rotated and translated
|
|
// by a random amount. PubChem puts them both in their inertial frame which
|
|
// makes things too easy.
|
|
auto tagrisso =
|
|
R"(C=CC(=O)Nc1cc(Nc2nccc(-c3cn(C)c4ccccc34)n2)c(OC)cc1N(C)CCN(C)C |(-0.9161,3.8415,-2.9811;0.1848,3.1933,-2.588;0.1064,1.7789,-2.12;-0.9619,1.1797,-2.0847;1.3654,1.2872,-1.7553;1.6841,0.0144,-1.273;0.6638,-0.9235,-1.1146;0.9578,-2.1997,-0.6343;-0.0813,-3.1358,-0.4783;-1.4556,-2.9979,-0.1847;-2.1716,-4.1359,-0.1085;-3.4803,-3.9673,0.173;-4.0689,-2.7353,0.3728;-3.2269,-1.647,0.2676;-3.7311,-0.317,0.4568;-5.0275,0.0291,0.153;-5.1887,1.3569,0.4454;-6.4231,2.0889,0.2595;-4.0141,1.8811,0.9361;-3.7121,3.1796,1.3615;-2.4139,3.4249,1.8179;-1.4588,2.4106,1.8467;-1.7752,1.1164,1.4181;-3.0776,0.8453,0.9537;-1.9103,-1.7423,-0.011;2.2723,-2.5382,-0.3127;2.58,-3.7798,0.1575;2.539,-3.9651,1.571;3.2927,-1.6003,-0.4713;2.9986,-0.324,-0.9514;4.0475,0.61,-1.1047;4.7738,0.6956,-2.3546;4.4021,1.497,-0.0162;5.4401,0.8254,0.8736;5.8294,1.7155,1.9601;4.8213,1.7057,3.0218;7.1361,1.3324,2.4981)|)"_smiles;
|
|
REQUIRE(tagrisso);
|
|
auto iressa =
|
|
R"(COc1cc2ncnc(Nc3ccc(F)c(Cl)c3)c2cc1OCCCN1CCOCC1 |(11.4672,-0.467948,5.63989;12.0133,0.532631,6.49693;11.2039,1.5801,6.81985;11.2014,2.71958,6.00975;10.3926,3.81652,6.29699;10.4038,4.90395,5.50623;9.58889,5.91871,5.85946;8.76443,5.96486,6.91838;8.77814,4.86059,7.68868;7.92337,4.86224,8.81914;7.44878,5.8925,9.64622;8.22182,7.03851,9.85619;7.75051,8.06265,10.6777;6.50441,7.94546,11.2936;6.06567,8.93802,12.0809;5.72932,6.80403,11.0875;4.19056,6.65372,11.8447;6.20047,5.78015,10.2656;9.57161,3.74547,7.43436;9.56851,2.60328,8.25407;10.3868,1.52933,7.93769;10.3797,0.419365,8.74203;11.3064,0.402096,9.81907;10.7104,-0.399165,10.9685;9.40938,0.22121,11.4678;9.64205,1.59049,11.9223;8.38006,2.22985,12.3199;8.64991,3.65266,12.8011;9.56883,3.64192,13.8942;10.8103,3.05101,13.5078;10.5931,1.61394,13.0425)|)"_smiles;
|
|
REQUIRE(iressa);
|
|
GaussianShape::ShapeOverlayOptions opts;
|
|
opts.optimMode = GaussianShape::OptimMode::SHAPE_PLUS_COLOR_SCORE;
|
|
opts.startMode = GaussianShape::StartMode::A_LA_PUBCHEM;
|
|
opts.nSteps = 100;
|
|
GaussianShape::ShapeInputOptions shapeOpts;
|
|
shapeOpts.allCarbonRadii = false;
|
|
auto scores = GaussianShape::AlignMolecule(*tagrisso, *iressa, shapeOpts,
|
|
shapeOpts, nullptr, opts);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.331, 0.005));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.572, 0.005));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.090, 0.005));
|
|
auto rescores = GaussianShape::ScoreMolecule(*tagrisso, *iressa, shapeOpts,
|
|
shapeOpts, opts);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(rescores[0], 0.005));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(rescores[1], 0.005));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(rescores[2], 0.005));
|
|
auto aligned_iressa =
|
|
"COc1cc2ncnc(Nc3ccc(F)c(Cl)c3)c2cc1OCCCN1CCOCC1 |(3.08453,-4.88523,0.170077;2.29914,-4.34091,-0.888589;1.15638,-3.68668,-0.538328;-0.040292,-4.40272,-0.438557;-1.23492,-3.78034,-0.0843727;-2.37618,-4.48548,0.00635958;-3.48492,-3.80191,0.355683;-3.57688,-2.48924,0.623248;-2.41657,-1.81353,0.522875;-2.46344,-0.42373,0.79642;-3.47407,0.538362,0.642364;-4.42522,0.402938,-0.373507;-5.42983,1.35852,-0.526776;-5.48774,2.45427,0.334513;-6.45888,3.36454,0.173853;-4.54106,2.59412,1.34956;-4.60745,3.94414,2.41576;-3.53677,1.63825,1.50308;-1.2037,-2.3998,0.172165;-0.00444866,-1.6727,0.0738388;1.16652,-2.3252,-0.281314;2.33196,-1.60985,-0.376552;2.6352,-1.04403,-1.64422;3.4233,0.241654,-1.43364;2.62275,1.26418,-0.633414;1.37651,1.58654,-1.32523;0.554317,2.50073,-0.520411;-0.734405,2.83149,-1.26777;-0.437359,3.41523,-2.53679;0.334793,2.52057,-3.33873;1.64904,2.18104,-2.64136)|"_smiles;
|
|
REQUIRE(aligned_iressa);
|
|
CHECK(checkMolsHaveRoughlySameCoords(*iressa, *aligned_iressa));
|
|
}
|
|
|
|
TEST_CASE("Optimise in place") {
|
|
// These are 2 ligands used by Andy Grant and Co in their original paper
|
|
// https://onlinelibrary.wiley.com/doi/10.1002/(SICI)1096-987X(19961115)17:14%3C1653::AID-JCC7%3E3.0.CO;2-K
|
|
// Ligands as extracted from PDB, with a bit of munging to get them as
|
|
// SMILES strings (downloaded the Ideal ligand structures from RCSB
|
|
// as SDFs and transferred the corresponding atom coords from 3tmn and 1tmn).
|
|
auto pdb_trp_3tmn =
|
|
R"(N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2 |(37.935,40.394,-3.825;39.119,39.593,-4.13;38.758,38.486,-5.101;37.526,38.337,-5.395;39.716,37.852,-5.605;39.883,39.108,-2.906;39.086,38.098,-2.209;38.093,38.363,-1.34;37.565,37.179,-0.881;38.201,36.136,-1.471;39.193,36.684,-2.308;40.015,35.812,-3.036;39.846,34.441,-2.913;38.844,33.933,-2.075;38.015,34.752,-1.333),wU:1.0|)"_smiles;
|
|
REQUIRE(pdb_trp_3tmn);
|
|
auto pdb_0zn_1tmn =
|
|
R"([C@H](CCc1ccccc1)(C(=O)O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2)CC(C)C |(35.672,41.482,-5.722;34.516,40.842,-6.512;34.843,39.355,-6.7;33.819,38.475,-7.45;33.825,38.414,-8.838;32.951,37.553,-9.53;32.064,36.747,-8.81;32.096,36.799,-7.402;32.985,37.656,-6.73;35.934,42.778,-6.452;36.833,42.858,-7.316;35.175,43.735,-6.275;35.516,41.561,-4.218;36.707,42.096,-3.513;38.055,41.449,-3.859;39.11,42.138,-3.959;37.975,40.129,-3.983;39.134,39.277,-4.298;38.825,38.04,-5.133;37.649,37.934,-5.605;39.788,37.369,-5.652;39.985,38.945,-3.037;39.221,37.953,-2.164;37.934,37.961,-1.823;37.579,36.695,-1.314;38.63,35.975,-1.286;39.736,36.771,-1.642;41.052,36.341,-1.48;41.213,35.042,-0.964;40.095,34.215,-0.69;38.765,34.665,-0.855;36.506,41.966,-2.002;37.6,42.757,-1.31;37.546,44.225,-1.728;37.408,42.58,0.19),wD:0.0,wU:17.21,13.33|)"_smiles;
|
|
REQUIRE(pdb_0zn_1tmn);
|
|
// This is the overlay produced by the first test below, to make sure we
|
|
// haven't broken anything.
|
|
auto ov_pdb_0zn_1tmn =
|
|
R"(CC(C)C[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O |(38.4182,43.8068,-0.910588;38.2709,42.2972,-0.731075;38.1304,41.9045,0.733229;37.0364,41.7932,-1.45451;37.1781,42.1406,-2.93763;35.8859,41.9023,-3.62687;35.9519,42.0509,-5.13225;34.6741,41.7191,-5.92414;34.7628,40.2524,-6.36478;33.5811,39.6611,-7.16439;33.5076,39.8293,-8.54156;32.4798,39.2259,-9.29221;31.5187,38.4455,-8.64246;31.6293,38.2599,-7.2498;32.6704,38.8605,-6.52059;36.3695,43.3994,-5.66929;37.2254,43.4931,-6.57465;35.7737,44.4114,-5.28982;38.3937,41.376,-3.47909;39.5342,41.9164,-3.54877;38.1091,40.1191,-3.80052;39.1087,39.1759,-4.32928;39.9624,38.5242,-3.20191;39.1024,37.5196,-2.43949;37.8503,37.6527,-2.00683;37.3343,36.383,-1.67591;38.2646,35.5274,-1.83827;38.2218,34.1585,-1.6274;39.4752,33.5046,-1.63354;40.6899,34.1995,-1.85784;40.7011,35.5753,-2.15222;39.4587,36.2072,-2.14728;38.5746,38.1494,-5.32118;37.3737,38.2894,-5.71533;39.3977,37.4441,-6.00821),wD:6.6,wU:4.3,21.22|)"_smiles;
|
|
auto initScores = GaussianShape::ScoreMolecule(*pdb_trp_3tmn, *pdb_0zn_1tmn);
|
|
CHECK_THAT(initScores[0], Catch::Matchers::WithinAbs(0.307, 0.001));
|
|
CHECK_THAT(initScores[1], Catch::Matchers::WithinAbs(0.349, 0.001));
|
|
CHECK_THAT(initScores[2], Catch::Matchers::WithinAbs(0.265, 0.001));
|
|
// The PDB atom order isn't canonical, so bounce in and out of SMILES
|
|
// to make it easier to check.
|
|
auto canon_probe =
|
|
v2::SmilesParse::MolFromSmiles(MolToCXSmiles(*pdb_0zn_1tmn));
|
|
{
|
|
// This should just tweak the input overlay.
|
|
GaussianShape::ShapeOverlayOptions opts;
|
|
opts.startMode = GaussianShape::StartMode::ROTATE_0;
|
|
opts.normalize = false;
|
|
GaussianShape::ShapeInputOptions shapeOpts;
|
|
ROMol cp(*canon_probe);
|
|
RDGeom::Transform3D xform;
|
|
auto scores = GaussianShape::AlignMolecule(*pdb_trp_3tmn, cp, shapeOpts,
|
|
shapeOpts, &xform, opts);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.322, 0.001));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.396, 0.001));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.247, 0.001));
|
|
CHECK(checkMolsHaveRoughlySameCoords(cp, *ov_pdb_0zn_1tmn));
|
|
}
|
|
{
|
|
// With default settings, it does a poor job.
|
|
GaussianShape::ShapeOverlayOptions opts;
|
|
GaussianShape::ShapeInputOptions shapeOpts;
|
|
ROMol cp(*canon_probe);
|
|
auto scores = GaussianShape::AlignMolecule(*pdb_trp_3tmn, cp, shapeOpts,
|
|
shapeOpts, nullptr, opts);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.201, 0.001));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.364, 0.001));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.039, 0.001));
|
|
}
|
|
{
|
|
// And with reference as a shape the same
|
|
GaussianShape::ShapeOverlayOptions opts;
|
|
opts.startMode = GaussianShape::StartMode::ROTATE_0;
|
|
opts.normalize = false;
|
|
GaussianShape::ShapeInputOptions shapeOpts;
|
|
auto refShape = GaussianShape::ShapeInput(*pdb_trp_3tmn, -1, shapeOpts);
|
|
ROMol cp(*canon_probe);
|
|
RDGeom::Transform3D xform;
|
|
auto scores =
|
|
GaussianShape::AlignMolecule(refShape, cp, shapeOpts, &xform, opts);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.322, 0.001));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.396, 0.001));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.247, 0.001));
|
|
CHECK(checkMolsHaveRoughlySameCoords(cp, *ov_pdb_0zn_1tmn));
|
|
MolTransforms::transformConformer(cp.getConformer(), xform);
|
|
ROMol cp1(*canon_probe);
|
|
MolTransforms::transformConformer(cp1.getConformer(), xform);
|
|
CHECK(checkMolsHaveRoughlySameCoords(cp1, *ov_pdb_0zn_1tmn));
|
|
}
|
|
{
|
|
// And with both as shapes
|
|
GaussianShape::ShapeOverlayOptions opts;
|
|
opts.startMode = GaussianShape::StartMode::ROTATE_0;
|
|
opts.normalize = false;
|
|
GaussianShape::ShapeInputOptions shapeOpts;
|
|
auto refShape = GaussianShape::ShapeInput(*pdb_trp_3tmn, -1, shapeOpts);
|
|
auto fitShape = GaussianShape::ShapeInput(*canon_probe, -1, shapeOpts);
|
|
RDGeom::Transform3D xform;
|
|
auto scores = GaussianShape::AlignShape(refShape, fitShape, &xform, opts);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.322, 0.001));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.396, 0.001));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.247, 0.001));
|
|
auto cp = fitShape.shapeToMol(false);
|
|
CHECK(checkMolsHaveRoughlySameCoords(*cp, *ov_pdb_0zn_1tmn));
|
|
}
|
|
}
|
|
|
|
TEST_CASE("Fragment Mode") {
|
|
// On the PDB overlay.
|
|
auto pdb_trp_3tmn =
|
|
R"(N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2 |(37.935,40.394,-3.825;39.119,39.593,-4.13;38.758,38.486,-5.101;37.526,38.337,-5.395;39.716,37.852,-5.605;39.883,39.108,-2.906;39.086,38.098,-2.209;38.093,38.363,-1.34;37.565,37.179,-0.881;38.201,36.136,-1.471;39.193,36.684,-2.308;40.015,35.812,-3.036;39.846,34.441,-2.913;38.844,33.933,-2.075;38.015,34.752,-1.333),wU:1.0|)"_smiles;
|
|
REQUIRE(pdb_trp_3tmn);
|
|
auto pdb_0zn_1tmn =
|
|
R"([C@H](CCc1ccccc1)(C(=O)O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2)CC(C)C |(35.672,41.482,-5.722;34.516,40.842,-6.512;34.843,39.355,-6.7;33.819,38.475,-7.45;33.825,38.414,-8.838;32.951,37.553,-9.53;32.064,36.747,-8.81;32.096,36.799,-7.402;32.985,37.656,-6.73;35.934,42.778,-6.452;36.833,42.858,-7.316;35.175,43.735,-6.275;35.516,41.561,-4.218;36.707,42.096,-3.513;38.055,41.449,-3.859;39.11,42.138,-3.959;37.975,40.129,-3.983;39.134,39.277,-4.298;38.825,38.04,-5.133;37.649,37.934,-5.605;39.788,37.369,-5.652;39.985,38.945,-3.037;39.221,37.953,-2.164;37.934,37.961,-1.823;37.579,36.695,-1.314;38.63,35.975,-1.286;39.736,36.771,-1.642;41.052,36.341,-1.48;41.213,35.042,-0.964;40.095,34.215,-0.69;38.765,34.665,-0.855;36.506,41.966,-2.002;37.6,42.757,-1.31;37.546,44.225,-1.728;37.408,42.58,0.19),wD:0.0,wU:17.21,13.33|)"_smiles;
|
|
REQUIRE(pdb_0zn_1tmn);
|
|
GaussianShape::ShapeOverlayOptions opts;
|
|
opts.nSteps = 100;
|
|
opts.startMode = GaussianShape::StartMode::ROTATE_180_FRAGMENT;
|
|
opts.optimMode = GaussianShape::OptimMode::SHAPE_PLUS_COLOR_SCORE;
|
|
auto probeShape = GaussianShape::ShapeInput(*pdb_trp_3tmn, -1);
|
|
auto refShape = GaussianShape::ShapeInput(*pdb_0zn_1tmn, -1);
|
|
RDGeom::Transform3D xform;
|
|
// Use the smaller molecule as the probe
|
|
auto scores = GaussianShape::AlignShape(refShape, probeShape, &xform, opts);
|
|
// These are close to the values above for starting from the xtal structures.
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(0.332, 0.005));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(0.413, 0.005));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.251, 0.005));
|
|
}
|
|
|
|
TEST_CASE("custom feature points") {
|
|
auto m1 =
|
|
"O=CC=O |(-1.75978,0.148897,0;-0.621382,-0.394324,0;0.624061,0.3656,.1;1.7571,-0.120174,.1)|"_smiles;
|
|
SECTION("using shapes") {
|
|
auto shape1 = GaussianShape::ShapeInput(*m1, -1);
|
|
// each carbonyl O gets one feature:
|
|
CHECK(shape1.getCoords().size() == 24);
|
|
GaussianShape::ShapeInputOptions opts2;
|
|
opts2.customFeatures = GaussianShape::CustomFeatures{
|
|
{1, RDGeom::Point3D(-1.75978, 0.148897, 0), 1.0},
|
|
{2, RDGeom::Point3D(1.7571, -0.120174, 0.1), 1.0}};
|
|
auto shape2 = GaussianShape::ShapeInput(*m1, -1, opts2);
|
|
CHECK(shape2.getCoords().size() == 24);
|
|
|
|
{
|
|
// confirm that we don't add the features if not requested.
|
|
GaussianShape::ShapeInputOptions topts;
|
|
topts.customFeatures = GaussianShape::CustomFeatures{
|
|
{1, RDGeom::Point3D(-1.75978, 0.148897, 0), 1.0},
|
|
{2, RDGeom::Point3D(1.7571, -0.120174, 0.1), 1.0}};
|
|
topts.useColors = false;
|
|
auto tshape = GaussianShape::ShapeInput(*m1, -1, topts);
|
|
CHECK(tshape.getCoords().size() == 16);
|
|
}
|
|
|
|
// we'll swap the features on the second shape so that the alignment has to
|
|
// be inverted
|
|
GaussianShape::ShapeInputOptions opts3;
|
|
opts3.customFeatures = GaussianShape::CustomFeatures{
|
|
{2, RDGeom::Point3D(-1.75978, 0.148897, 0), 1.0},
|
|
{1, RDGeom::Point3D(1.7571, -0.120174, 0.1), 1.0}};
|
|
|
|
auto m2 = ROMol(*m1);
|
|
auto shape3 = GaussianShape::ShapeInput(m2, -1, opts3);
|
|
CHECK(shape3.getCoords().size() == 24);
|
|
GaussianShape::ShapeOverlayOptions overlayOpts;
|
|
overlayOpts.optParam = 0.5;
|
|
RDGeom::Transform3D xform;
|
|
auto scores = AlignShape(shape2, shape3, &xform, overlayOpts);
|
|
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(1.000, 0.001));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(1.000, 0.001));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.999, 0.001));
|
|
CHECK(shape3.getCoords()[0] > 0); // x coord of first atom
|
|
CHECK(shape3.getCoords()[3 * 4] < 0); // x coord of fourth atom
|
|
|
|
auto conf = m2.getConformer(-1);
|
|
MolTransforms::transformConformer(conf, xform);
|
|
CHECK(conf.getAtomPos(0).x > 0);
|
|
CHECK(conf.getAtomPos(3).x < 0);
|
|
}
|
|
SECTION("using molecules") {
|
|
GaussianShape::ShapeInputOptions opts2;
|
|
opts2.customFeatures = GaussianShape::CustomFeatures{
|
|
{1, RDGeom::Point3D(-1.75978, 0.148897, 0), 1.0},
|
|
{2, RDGeom::Point3D(1.7571, -0.120174, 0.1), 1.0}};
|
|
|
|
auto m2 = ROMol(*m1);
|
|
// we'll swap the features on the second shape so that the alignment has to
|
|
// be inverted
|
|
GaussianShape::ShapeInputOptions opts3;
|
|
opts3.customFeatures = GaussianShape::CustomFeatures{
|
|
{2, RDGeom::Point3D(-1.75978, 0.148897, 0), 1.0},
|
|
{1, RDGeom::Point3D(1.7571, -0.120174, 0.1), 1.0}};
|
|
|
|
GaussianShape::ShapeOverlayOptions overlayOpts;
|
|
overlayOpts.optParam = 0.5;
|
|
std::vector<float> matrix(12, 0.0);
|
|
auto scores = AlignMolecule(*m1, m2, opts2, opts3, nullptr, overlayOpts);
|
|
CHECK_THAT(scores[0], Catch::Matchers::WithinAbs(1.000, 0.001));
|
|
CHECK_THAT(scores[1], Catch::Matchers::WithinAbs(1.000, 0.001));
|
|
CHECK_THAT(scores[2], Catch::Matchers::WithinAbs(0.999, 0.001));
|
|
auto conf = m2.getConformer(-1);
|
|
CHECK(conf.getAtomPos(0).x > 0);
|
|
CHECK(conf.getAtomPos(3).x < 0);
|
|
}
|
|
}
|
|
|
|
TEST_CASE("Non-standard radii") {
|
|
auto m1 =
|
|
"[Xe]c1ccccc1 |(0.392086,-2.22477,0.190651;0.232269,-1.38667,0.118385;-1.06274,-0.918982,0.0342466;-1.26098,0.446053,-0.0811879;-0.244035,1.36265,-0.11691;1.05134,0.875929,-0.031248;1.28797,-0.499563,0.0864097),atomProp:0.dummyLabel.*|"_smiles;
|
|
GaussianShape::ShapeInputOptions shapeOpts;
|
|
shapeOpts.useColors = false;
|
|
shapeOpts.allCarbonRadii = false;
|
|
auto shape1 = GaussianShape::ShapeInput(*m1, -1, shapeOpts);
|
|
|
|
CHECK(shape1.getCoords().size() == 28);
|
|
CHECK_THAT(shape1.getShapeVolume(),
|
|
Catch::Matchers::WithinAbs(387.396, 0.005));
|
|
// mol1 with atom 4 with an N radius and a bigger Xe.
|
|
shapeOpts.atomRadii =
|
|
std::vector<std::pair<unsigned int, double>>{{0, 2.5}, {4, 1.55}};
|
|
shapeOpts.allCarbonRadii = false;
|
|
auto shape2 = GaussianShape::ShapeInput(*m1, -1, shapeOpts);
|
|
CHECK_THAT(shape2.getShapeVolume(),
|
|
Catch::Matchers::WithinAbs(425.051, 0.005));
|
|
|
|
// Corresponding pyridine derivative.
|
|
auto m2 =
|
|
"[Xe]c1ccncc1 |(0.392086,-2.22477,0.190651;0.232269,-1.38667,0.118385;-1.06274,-0.918982,0.0342466;-1.26098,0.446053,-0.0811879;-0.244035,1.36265,-0.11691;1.05134,0.875929,-0.031248;1.28797,-0.499563,0.0864097),atomProp:0.dummyLabel.*|"_smiles;
|
|
auto shape3 = GaussianShape::ShapeInput(*m2, -1, shapeOpts);
|
|
CHECK(shape3.getShapeVolume() == shape2.getShapeVolume());
|
|
}
|
|
|
|
TEST_CASE("Shape subset") {
|
|
auto m1 =
|
|
"c1ccc(-c2ccccc2)cc1 |(-3.26053,-0.0841607,-0.741909;-2.93383,0.123873,0.593407;-1.60713,0.377277,0.917966;-0.644758,0.654885,-0.0378428;0.743308,0.219134,0.168663;1.82376,1.0395,-0.0112769;3.01462,0.695405,0.613858;3.18783,-0.589771,1.09649;2.15761,-1.50458,1.01949;0.988307,-1.1313,0.385783;-1.1048,0.797771,-1.34022;-2.39754,0.435801,-1.69921)|"_smiles;
|
|
REQUIRE(m1);
|
|
GaussianShape::ShapeInputOptions shapeOpts;
|
|
shapeOpts.atomSubset = std::vector<unsigned int>{0, 1, 2, 3, 10, 11};
|
|
auto partShape = GaussianShape::ShapeInput(*m1, -1, shapeOpts);
|
|
CHECK(partShape.getCoords().size() == 28);
|
|
CHECK_THAT(partShape.getShapeVolume(),
|
|
Catch::Matchers::WithinAbs(261.166, 0.005));
|
|
CHECK_THAT(partShape.getColorVolume(),
|
|
Catch::Matchers::WithinAbs(5.316, 0.005));
|
|
|
|
shapeOpts.atomSubset.clear();
|
|
auto wholeShape = GaussianShape::ShapeInput(*m1, -1, shapeOpts);
|
|
CHECK(wholeShape.getCoords().size() == 56);
|
|
CHECK_THAT(wholeShape.getShapeVolume(),
|
|
Catch::Matchers::WithinAbs(556.266, 0.005));
|
|
CHECK_THAT(wholeShape.getColorVolume(),
|
|
Catch::Matchers::WithinAbs(10.631, 0.005));
|
|
}
|
|
|
|
// These are LOBSTER structures 437_A_355, YIW_A_1353, LSA_A_503, SU0_A_263,
|
|
// VHC_A_1, 40Z_A_301, 0J8_A_1401, 5QQ_A_1401, 054_A_578, 053_A_578
|
|
// respectively. LOBSTER is published
|
|
// https://doi.org/10.1007/s10822-024-00581-1 from the Rarey and BioSolveIT
|
|
// group.
|
|
std::
|
|
vector<std::string>
|
|
lobstersText =
|
|
{
|
|
"CC(C)(C)c1cc(NC(=O)Nc2cccc3ccccc23)n(-c2ccc(CO)cc2)n1 |(4.1858,1.2187,12.6749;3.4917,2.128,11.6409;4.5532,3.0576,11.0244;2.9098,1.2685,10.5255;2.3016,2.8612,12.2277;1.3306,2.2548,13.0356;0.4334,3.2937,13.302;-0.7316,3.3518,14.0275;-0.978,2.5581,15.0932;-0.147,1.7378,15.4901;-2.1645,2.6924,15.6938;-2.626,2.0319,16.8298;-1.8457,2.1016,18.0083;-2.2654,1.5179,19.2117;-3.4858,0.8316,19.2546;-4.2646,0.7339,18.1056;-5.4724,0.0393,18.1895;-6.2813,-0.103,17.0695;-5.8756,0.4693,15.8666;-4.6776,1.1996,15.7839;-3.8502,1.3304,16.8984;0.8824,4.3943,12.6425;0.3828,5.6491,12.5902;-0.1458,6.3636,13.6677;-0.6231,7.6713,13.5508;-0.5802,8.3258,12.3036;-1.1083,9.738,12.1288;-0.2929,10.4745,11.2057;-0.0699,7.6584,11.21;0.4028,6.3542,11.3691;2.0606,4.1572,11.9546)|",
|
|
"CC(C)c1nnc2ccc(Sc3ccccc3CNC(=O)Nc3cc(C(C)(C)C)nn3-c3ccccc3)cn12 |(-2.677,-1.147,25.057;-1.383,-1.713,24.501;-0.937,-2.645,25.64;-1.654,-2.496,23.218;-1.533,-3.804,23.035;-1.814,-4.126,21.82;-2.125,-3.054,21.15;-2.484,-2.842,19.8;-2.737,-1.521,19.397;-2.633,-0.45,20.292;-2.934,1.2,19.817;-4.086,0.989,18.473;-5.306,0.233,18.595;-6.145,0.057,17.523;-5.802,0.63,16.3;-4.651,1.427,16.155;-3.805,1.585,17.237;-2.532,2.33,17.092;-2.317,3.124,15.849;-1.208,2.896,15.139;-0.293,2.051,15.461;-0.934,3.704,14.164;0.194,3.633,13.319;1.093,2.626,13.06;2.064,3.138,12.153;3.254,2.438,11.547;2.765,1.497,10.446;4.297,3.407,10.979;3.923,1.592,12.556;1.755,4.357,11.974;0.557,4.674,12.592;0.026,5.998,12.604;-0.011,6.769,11.405;-0.52,8.07,11.439;-0.946,8.61,12.635;-0.914,7.879,13.819;-0.396,6.572,13.782;-2.292,-0.677,21.581;-2.025,-1.986,22.016)|",
|
|
"O=S1(=O)N=C(O)c2ccccc21 |(-5.7089,1.0252,18.4004;-6.3943,1.0779,17.1227;-7.8251,0.8757,17.0645;-5.6185,0.1418,15.9961;-4.8784,0.7874,15.1629;-4.3563,0.192,14.2273;-5.1972,2.2654,15.1438;-4.6774,3.2806,14.3416;-5.0543,4.5982,14.6171;-5.8378,4.8973,15.7426;-6.3084,3.8774,16.5767;-5.9587,2.5637,16.2652)|",
|
|
"COc1ccc2c(CC(=O)Nc3ccc(S(N)(=O)=O)cc3)cc(=O)oc2c1 |(-2.8164,14.7062,11.3592;-3.6624,13.537,11.2643;-3.2822,12.2442,11.6717;-3.8543,11.0312,10.9854;-3.454,9.7632,11.3397;-2.4737,9.5893,12.4478;-2.0245,8.2354,12.8485;-2.4284,7.0271,12.0534;-3.4577,6.2276,12.8381;-4.6459,6.5341,12.9744;-2.9341,5.1799,13.652;-3.8043,4.2751,14.3593;-3.0353,3.1465,14.8909;-3.6696,2.1888,15.6247;-5.1279,2.3197,15.867;-5.8526,1.0165,16.8148;-5.1597,-0.2684,16.1766;-7.2644,1.0484,16.6895;-5.3596,1.2234,18.1529;-5.863,3.3573,15.3579;-5.1676,4.4008,14.5479;-1.2733,8.1678,14.0258;-0.8262,9.3446,14.6451;-0.1397,9.3025,15.6623;-1.0563,10.6342,14.1829;-1.9446,10.7231,13.0793;-2.3948,12.0761,12.7036)|",
|
|
"Cc1cc(C)c2cc1C(=O)NCCCOc1cccc(c1)Sc1cc-2nc(N)n1 |(73.8435,34.0723,26.5156;72.3815,34.1628,26.0388;71.6766,32.9652,25.9327;70.3451,32.9485,25.4823;69.6347,31.5936,25.3834;69.7284,34.1492,25.0935;70.4497,35.3542,25.1896;71.7747,35.3826,25.6823;72.4585,36.7442,25.8391;73.1172,37.0066,26.8611;72.1633,37.6292,24.8945;72.7135,39.0047,24.8716;71.7025,40.047,24.3677;71.3796,39.8568,22.8758;70.4153,38.7939,22.9499;69.8006,38.3095,21.8404;70.2406,38.4827,20.5148;69.5441,37.8479,19.489;68.407,37.0853,19.7393;68.0155,36.8722,21.0628;68.6923,37.5061,22.0951;66.5592,35.8914,21.365;66.9463,35.055,22.8617;68.2573,34.8374,23.3077;68.4281,34.247,24.558;67.3421,33.831,25.243;66.0874,33.9792,24.7404;65.0509,33.4765,25.428;65.8935,34.6016,23.5436)|",
|
|
"Cc1c2c(n3c1CCN(Cc1ccco1)c1cc(C(N)=O)c(Cl)cc1-3)CC(C)(C)CC2=O |(74.8244,36.0896,26.0638;73.6879,35.186,25.6743;73.8428,33.8098,25.2429;72.5848,33.3216,24.9555;71.6743,34.332,25.2034;72.3429,35.4561,25.6334;71.7112,36.7663,26.0021;70.9895,37.4573,24.8514;70.1361,36.585,24.0367;69.7698,37.0101,22.6942;70.4319,38.0048,21.8175;70.8144,39.2778,21.9818;71.3289,39.7044,20.7598;71.23,38.6778,19.9306;70.6882,37.6078,20.5486;69.5068,35.3697,24.5106;68.1241,35.239,24.3599;67.4459,34.0963,24.7908;65.9689,34.0392,24.5456;65.1976,33.5111,25.4835;65.5111,34.4884,23.4842;68.1905,33.0839,25.4012;67.4671,31.5959,25.9018;69.5536,33.1987,25.5786;70.2398,34.3166,25.103;72.2711,31.9512,24.4312;73.4524,31.2236,23.7805;73.1395,29.7332,23.6933;73.6857,31.7544,22.3618;74.7055,31.4432,24.6434;74.982,32.872,25.0594;76.1434,33.2319,25.2012)|",
|
|
"O=[N+]([O-])c1cccc(CNc2nc(C(F)(F)F)nc3ncc(-c4cnn(C5CCNCC5)c4)cc23)c1 |(-1.438,-13.226,20.761;-2.668,-13.702,20.695;-3.225,-14.278,21.715;-3.449,-13.606,19.5;-4.865,-13.703,19.611;-5.66,-13.615,18.465;-5.057,-13.44,17.21;-3.642,-13.329,17.113;-2.985,-13.176,15.754;-3.208,-14.453,15.102;-2.183,-15.47,15.231;-1.174,-15.247,16.105;-0.207,-16.166,16.24;0.913,-15.872,17.233;1.607,-16.968,17.501;1.653,-14.932,16.679;0.431,-15.434,18.382;-0.155,-17.307,15.532;-1.134,-17.587,14.626;-1.051,-18.759,13.937;-2.004,-19.081,13.034;-3.067,-18.213,12.807;-4.134,-18.597,11.829;-4.958,-17.727,11.105;-5.807,-18.503,10.373;-5.518,-19.836,10.648;-6.22,-21.008,10.059;-7.613,-21.132,10.635;-8.385,-22.302,9.993;-8.344,-22.271,8.528;-7.465,-21.299,7.857;-6.163,-20.922,8.548;-4.513,-19.902,11.543;-3.18,-16.987,13.52;-2.183,-16.667,14.458;-2.84,-13.422,18.253)|",
|
|
"Fc1ccc(-c2cnc3nnc(C(F)(F)c4ccc5ncccc5c4)n3n2)cc1 |(-8.9341,-13.5345,15.2941;-7.8624,-13.6169,16.1019;-8.0323,-13.604,17.4747;-6.927,-13.6949,18.3088;-5.6563,-13.7867,17.7687;-4.5363,-13.8655,18.5962;-4.6798,-14.0273,19.9861;-3.5769,-14.1,20.7695;-2.3321,-14.0007,20.1927;-1.0691,-14.049,20.7489;-0.1759,-13.9183,19.7353;-0.8597,-13.8052,18.581;-0.2877,-13.6262,17.1957;1.0077,-13.3321,17.3153;-0.932,-12.6293,16.5758;-0.3953,-14.89,16.3793;0.3679,-16.0044,16.7321;0.2944,-17.1762,15.9833;-0.5658,-17.2197,14.8472;-0.6484,-18.3768,14.1035;-1.4592,-18.4618,13.0237;-2.2424,-17.3707,12.6345;-2.1971,-16.184,13.3658;-1.3263,-16.1253,14.5037;-1.2424,-14.9308,15.2731;-2.1994,-13.8502,18.8681;-3.3091,-13.7741,18.0449;-5.4848,-13.7974,16.3944;-6.5897,-13.7169,15.5608)|",
|
|
"Nc1cc(Cn2c(C(=O)O)c(-n3c(=O)[nH]c4cscc4c3=O)c3cc(C(F)(F)F)ccc32)ccn1 |(29.5323,45.8636,43.104;28.8655,44.7866,42.5152;27.6833,44.3191,43.0964;27.0256,43.2322,42.5026;25.769,42.5937,43.0062;25.1539,43.3311,44.0877;24.4106,44.4698,43.8927;24.1642,45.0354,42.563;23.9009,46.3564,42.5697;24.0503,44.4039,41.5301;23.9917,44.8584,45.1623;23.2031,45.9947,45.3911;21.8869,45.9724,44.834;21.3954,44.9674,44.2853;21.1644,47.1439,44.9613;21.7067,48.2779,45.5571;21.0928,49.4972,45.696;22.1115,50.6335,46.4923;23.3622,49.4671,46.6456;23.0143,48.2553,46.0988;23.8418,47.054,46.0577;24.9808,47.0096,46.5158;24.5049,43.9455,46.1213;24.4196,43.8288,47.5202;25.0722,42.7404,48.1424;25.0173,42.5333,49.6217;24.5189,41.3151,49.9335;26.2412,42.5919,50.1868;24.2862,43.4348,50.3041;25.7949,41.7994,47.3917;25.8973,41.9011,46.0107;25.2386,42.9843,45.4045;27.5907,42.6386,41.3749;28.7511,43.1735,40.8552;29.3972,44.2337,41.3948)|",
|
|
"Nc1cc(Cn2c(C(=O)O)c(-c3ccc[nH]c3=O)c3cc(C(F)(F)F)ccc32)ccn1 |(29.4427,46.05,43.4472;28.8505,44.9996,42.7518;27.6724,44.4529,43.2669;27.0734,43.3813,42.5955;25.8189,42.6999,43.052;25.2163,43.3606,44.2071;24.4581,44.4943,44.0838;24.1931,45.0901,42.7808;24.1204,46.4333,42.7998;23.8923,44.4562,41.7912;24.0461,44.8297,45.3707;23.2097,45.9536,45.7413;23.5041,46.7963,46.7667;22.6287,47.9099,47.1092;21.5037,48.1244,46.3872;21.1624,47.2732,45.3588;21.9195,46.1834,44.9822;21.563,45.4266,44.0641;24.5817,43.8725,46.2645;24.4958,43.6833,47.6538;25.1452,42.5857,48.2292;25.0531,42.3252,49.6881;24.5934,41.0857,49.9422;26.2447,42.4118,50.3073;24.2575,43.1875,50.3428;25.8943,41.6963,47.4464;25.9994,41.8646,46.0771;25.324,42.958,45.5057;27.6791,42.8877,41.4291;28.8324,43.5019,40.9842;29.4267,44.5435,41.6155)|",
|
|
};
|
|
std::vector<std::shared_ptr<RWMol>> lobsters;
|
|
void initLobsters() {
|
|
if (lobsters.empty()) {
|
|
for (const auto &text : lobstersText) {
|
|
lobsters.emplace_back(v2::SmilesParse::MolFromSmiles(text));
|
|
REQUIRE(lobsters.back());
|
|
}
|
|
}
|
|
}
|
|
|
|
TEST_CASE("Tversky") {
|
|
// Score the PDB overlay.
|
|
auto pdb_trp_3tmn =
|
|
R"(N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2 |(37.935,40.394,-3.825;39.119,39.593,-4.13;38.758,38.486,-5.101;37.526,38.337,-5.395;39.716,37.852,-5.605;39.883,39.108,-2.906;39.086,38.098,-2.209;38.093,38.363,-1.34;37.565,37.179,-0.881;38.201,36.136,-1.471;39.193,36.684,-2.308;40.015,35.812,-3.036;39.846,34.441,-2.913;38.844,33.933,-2.075;38.015,34.752,-1.333),wU:1.0|)"_smiles;
|
|
REQUIRE(pdb_trp_3tmn);
|
|
auto pdb_0zn_1tmn =
|
|
R"([C@H](CCc1ccccc1)(C(=O)O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2)CC(C)C |(35.672,41.482,-5.722;34.516,40.842,-6.512;34.843,39.355,-6.7;33.819,38.475,-7.45;33.825,38.414,-8.838;32.951,37.553,-9.53;32.064,36.747,-8.81;32.096,36.799,-7.402;32.985,37.656,-6.73;35.934,42.778,-6.452;36.833,42.858,-7.316;35.175,43.735,-6.275;35.516,41.561,-4.218;36.707,42.096,-3.513;38.055,41.449,-3.859;39.11,42.138,-3.959;37.975,40.129,-3.983;39.134,39.277,-4.298;38.825,38.04,-5.133;37.649,37.934,-5.605;39.788,37.369,-5.652;39.985,38.945,-3.037;39.221,37.953,-2.164;37.934,37.961,-1.823;37.579,36.695,-1.314;38.63,35.975,-1.286;39.736,36.771,-1.642;41.052,36.341,-1.48;41.213,35.042,-0.964;40.095,34.215,-0.69;38.765,34.665,-0.855;36.506,41.966,-2.002;37.6,42.757,-1.31;37.546,44.225,-1.728;37.408,42.58,0.19),wD:0.0,wU:17.21,13.33|)"_smiles;
|
|
REQUIRE(pdb_0zn_1tmn);
|
|
GaussianShape::ShapeOverlayOptions ovlyOpts;
|
|
GaussianShape::ShapeInputOptions inOpts;
|
|
auto tan_scores = GaussianShape::ScoreMolecule(*pdb_0zn_1tmn, *pdb_trp_3tmn);
|
|
CHECK_THAT(tan_scores[0], Catch::Matchers::WithinAbs(0.307, 0.001));
|
|
CHECK_THAT(tan_scores[1], Catch::Matchers::WithinAbs(0.349, 0.001));
|
|
CHECK_THAT(tan_scores[2], Catch::Matchers::WithinAbs(0.265, 0.001));
|
|
|
|
ovlyOpts.simAlpha = 0.95;
|
|
ovlyOpts.simBeta = 0.05;
|
|
auto ref_tversky = GaussianShape::ScoreMolecule(*pdb_0zn_1tmn, *pdb_trp_3tmn,
|
|
inOpts, inOpts, ovlyOpts);
|
|
CHECK_THAT(ref_tversky[0], Catch::Matchers::WithinAbs(0.362, 0.001));
|
|
CHECK_THAT(ref_tversky[1], Catch::Matchers::WithinAbs(0.383, 0.001));
|
|
CHECK_THAT(ref_tversky[2], Catch::Matchers::WithinAbs(0.342, 0.001));
|
|
|
|
ovlyOpts.simAlpha = 0.05;
|
|
ovlyOpts.simBeta = 0.95;
|
|
auto fit_tversky = GaussianShape::ScoreMolecule(*pdb_0zn_1tmn, *pdb_trp_3tmn,
|
|
inOpts, inOpts, ovlyOpts);
|
|
CHECK_THAT(fit_tversky[0], Catch::Matchers::WithinAbs(0.668, 0.001));
|
|
CHECK_THAT(fit_tversky[1], Catch::Matchers::WithinAbs(0.795, 0.001));
|
|
CHECK_THAT(fit_tversky[2], Catch::Matchers::WithinAbs(0.540, 0.001));
|
|
}
|
|
|
|
#ifdef RDK_USE_BOOST_SERIALIZATION
|
|
TEST_CASE("Serialization") {
|
|
auto m1 =
|
|
"[H]c1c([H])c([H])c([H])c([H])c1[H] |(-2.06264,-0.844763,-0.0261403;-1.04035,-0.481453,-0.0114878;-0.00743655,-1.41861,-0.0137121;-0.215455,-2.47997,-0.0295909;1.29853,-0.949412,0.00507497;2.12524,-1.65277,0.00390664;1.58501,0.395878,0.0254188;2.61997,0.704365,0.0394811;0.550242,1.31385,0.0273741;0.783172,2.37039,0.0434262;-0.763786,0.88847,0.00908113;-1.60557,1.58532,0.0100194)|"_smiles;
|
|
REQUIRE(m1);
|
|
GaussianShape::ShapeInputOptions shapeOpts;
|
|
shapeOpts.allCarbonRadii = false;
|
|
auto shape = GaussianShape::ShapeInput(*m1, -1, shapeOpts);
|
|
auto istr = shape.toString();
|
|
|
|
GaussianShape::ShapeInput shape2(istr);
|
|
CHECK(shape2.getCoords() == shape.getCoords());
|
|
CHECK(shape2.getTypes() == shape.getTypes());
|
|
CHECK(shape2.getNumAtoms() == shape.getNumAtoms());
|
|
CHECK(shape2.getNumFeatures() == shape.getNumFeatures());
|
|
CHECK(shape2.getNormalized() == shape.getNormalized());
|
|
CHECK(shape2.calcExtremes() == shape.calcExtremes());
|
|
CHECK(shape2.calcCanonicalRotation() == shape.calcCanonicalRotation());
|
|
CHECK(shape2.calcCanonicalTranslation() == shape.calcCanonicalTranslation());
|
|
CHECK(*shape2.getCarbonRadii() == *shape.getCarbonRadii());
|
|
CHECK_THAT(shape2.getShapeVolume(),
|
|
Catch::Matchers::WithinAbs(261.0145, 0.005));
|
|
CHECK_THAT(shape2.getColorVolume(), Catch::Matchers::WithinAbs(5.316, 0.005));
|
|
|
|
// Check it handles the case of no d_carbonRadii in the ShapeInput.
|
|
shapeOpts.allCarbonRadii = true;
|
|
auto shape3 = GaussianShape::ShapeInput(*m1, -1, shapeOpts);
|
|
auto istr2 = shape3.toString();
|
|
GaussianShape::ShapeInput shape4(istr2);
|
|
CHECK(!shape4.getCarbonRadii());
|
|
}
|
|
#endif
|
|
|
|
#ifdef RDK_TEST_MULTITHREADED
|
|
#include <thread>
|
|
#include <future>
|
|
|
|
namespace {
|
|
void runblock(
|
|
const std::vector<std::pair<std::shared_ptr<RWMol>, std::shared_ptr<RWMol>>>
|
|
&pairs,
|
|
unsigned int count, unsigned int idx,
|
|
std::vector<std::array<double, 3>> &test) {
|
|
for (unsigned int i = idx; i < pairs.size(); i += count) {
|
|
auto p1 = *pairs[i].first;
|
|
auto p2 = *pairs[i].second;
|
|
test[i] = GaussianShape::AlignMolecule(p1, p2);
|
|
}
|
|
}
|
|
} // namespace
|
|
|
|
TEST_CASE("multithreaded") {
|
|
initLobsters();
|
|
|
|
constexpr size_t numRepeats = 1000;
|
|
std::vector<std::pair<std::shared_ptr<RWMol>, std::shared_ptr<RWMol>>> pairs;
|
|
for (auto r = 0u; r < numRepeats; ++r) {
|
|
for (unsigned int i = 0; i < 10; i += 2) {
|
|
unsigned int l1 = i;
|
|
unsigned int l2 = i + 1;
|
|
pairs.emplace_back(lobsters[l1], lobsters[l2]);
|
|
}
|
|
}
|
|
// generate reference data
|
|
std::cerr << " generating reference data" << std::endl;
|
|
auto start = std::chrono::steady_clock::now();
|
|
std::vector<std::array<double, 3>> ref;
|
|
for (auto pr : pairs) {
|
|
auto p1 = *pr.first;
|
|
auto p2 = *pr.second;
|
|
auto norm_scores = GaussianShape::AlignMolecule(p1, p2);
|
|
|
|
ref.push_back(norm_scores);
|
|
}
|
|
auto end = std::chrono::steady_clock::now();
|
|
auto ref_time =
|
|
std::chrono::duration_cast<std::chrono::milliseconds>(end - start)
|
|
.count();
|
|
std::cerr << " reference time: " << ref_time << "ms" << std::endl;
|
|
|
|
// run the same calculations in parallel and check they match the reference
|
|
std::cerr << " parallel loop" << std::endl;
|
|
std::vector<std::array<double, 3>> test(pairs.size());
|
|
std::vector<unsigned int> idx(pairs.size());
|
|
std::iota(idx.begin(), idx.end(), 0);
|
|
auto start2 = std::chrono::steady_clock::now();
|
|
std::vector<std::future<void>> tg;
|
|
unsigned int count = 4;
|
|
for (unsigned int i = 0; i < count; ++i) {
|
|
tg.emplace_back(std::async(std::launch::async, runblock, pairs, count, i,
|
|
std::ref(test)));
|
|
}
|
|
for (auto &fut : tg) {
|
|
fut.get();
|
|
}
|
|
tg.clear();
|
|
auto end2 = std::chrono::steady_clock::now();
|
|
auto test_time =
|
|
std::chrono::duration_cast<std::chrono::milliseconds>(end2 - start2)
|
|
.count();
|
|
std::cerr << " parallel time: " << test_time << "ms" << std::endl;
|
|
CHECK(test == ref);
|
|
}
|
|
#endif
|