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// $Id: test1.cpp 1625 2011-01-13 04:22:56Z glandrum $
//
// Copyright (C) 2003-2006 Rational Discovery LLC
//
// @@ 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 <RDGeneral/Invariant.h>
#include <RDGeneral/utils.h>
#include <Geometry/Transform3D.h>
#include <iostream>
#include <GraphMol/RDKitBase.h>
#include <GraphMol/SmilesParse/SmilesParse.h>
#include <GraphMol/FileParsers/FileParsers.h>
#include <Geometry/point.h>
#include "MolTransforms.h"
using namespace RDKit;
using namespace MolTransforms;
bool comparePts(const RDGeom::Point3D &pt1, const RDGeom::Point3D &pt2, double tol=1.0e-4) {
RDGeom::Point3D tpt = pt1;
tpt -= pt2;
return (tpt.length() < tol);
}
void test1Canonicalization() {
ROMol *mol = SmilesToMol("C", 0, 1);
Conformer *conf = new Conformer(1);
conf->setAtomPos(0, RDGeom::Point3D(4.0, 5.0, 6.0));
int cid = mol->addConformer(conf, true);
RDGeom::Point3D pt = computeCentroid(*conf);
CHECK_INVARIANT(comparePts(pt, RDGeom::Point3D(4.0, 5.0, 6.0)), "");
RDGeom::Transform3D *trans = computeCanonicalTransform(*conf);
transformConformer(*conf, *trans);
CHECK_INVARIANT(comparePts(conf->getAtomPos(0), RDGeom::Point3D(0.0, 0.0, 0.0)), "");
conf->setAtomPos(0, RDGeom::Point3D(4.0, 5.0, 6.0));
canonicalizeConformer(*conf);
CHECK_INVARIANT(comparePts(conf->getAtomPos(0), RDGeom::Point3D(0.0, 0.0, 0.0)), "");
delete mol;
//delete conf;
delete trans;
// lets try two points now
mol = SmilesToMol("CC", 0, 1);
conf = new Conformer(2);
conf->setAtomPos(0, RDGeom::Point3D(0.0, 0.0, 0.0));
conf->setAtomPos(1, RDGeom::Point3D(1.5, 0.0, 0.0));
cid = mol->addConformer(conf, true);
trans = computeCanonicalTransform(*conf);
canonicalizeConformer(*conf);
CHECK_INVARIANT(comparePts(conf->getAtomPos(0), RDGeom::Point3D(-0.75, 0.0, 0.0)), "");
CHECK_INVARIANT(comparePts(conf->getAtomPos(1), RDGeom::Point3D(0.75, 0.0, 0.0)), "");
conf->setAtomPos(0, RDGeom::Point3D(0.0, 0.0, 0.0));
conf->setAtomPos(1, RDGeom::Point3D(0.0, 1.5, 0.0));
trans = computeCanonicalTransform(*conf);
canonicalizeConformer(*conf);
CHECK_INVARIANT(comparePts(conf->getAtomPos(0), RDGeom::Point3D(-0.75, 0.0, 0.0)), "");
CHECK_INVARIANT(comparePts(conf->getAtomPos(1), RDGeom::Point3D(0.75, 0.0, 0.0)), "");
delete mol;
delete trans;
mol = SmilesToMol("CC", 0, 1);
conf = new Conformer(2);
conf->setAtomPos(0, RDGeom::Point3D(0.0, 0.0, 0.0));
conf->setAtomPos(1, RDGeom::Point3D(1.5, 0.0, 0.0));
cid = mol->addConformer(conf, true);
trans = computeCanonicalTransform(*conf);
transformConformer(*conf, *trans);
canonicalizeConformer(*conf);
CHECK_INVARIANT(comparePts(conf->getAtomPos(0), RDGeom::Point3D(-0.75, 0.0, 0.0)), "");
CHECK_INVARIANT(comparePts(conf->getAtomPos(1), RDGeom::Point3D(0.75, 0.0, 0.0)), "");
delete mol;
delete trans;
mol = SmilesToMol("C1CC1", 0, 1);
conf = new Conformer(3);
conf->setAtomPos(0, RDGeom::Point3D(0.58, -0.66, -0.08));
conf->setAtomPos(1, RDGeom::Point3D(-0.88, -0.18, -0.04));
conf->setAtomPos(2, RDGeom::Point3D(.26, 0.82, 0.14));
cid = mol->addConformer(conf, true);
//trans = computeCanonicalTransform(*conf);
//transformConformer(*conf, *trans);
canonicalizeConformer(*conf);
CHECK_INVARIANT(comparePts(conf->getAtomPos(0), RDGeom::Point3D(-0.6418, 0.6158, 0.0)), "");
CHECK_INVARIANT(comparePts(conf->getAtomPos(1), RDGeom::Point3D(-0.2029, -0.8602, 0.0)), "");
CHECK_INVARIANT(comparePts(conf->getAtomPos(2), RDGeom::Point3D(0.8447, 0.2445, 0.0)), "");
MolToMolFile(*mol, "junk.mol", 0);
//CHECK_INVARIANT(comparePts(conf->getAtomPos(0), RDGeom::Point3D(-0.75, 0.0, 0.0)), "");
//CHECK_INVARIANT(comparePts(conf->getAtomPos(1), RDGeom::Point3D(0.75, 0.0, 0.0)), "");
delete mol;
std::string rdbase = getenv("RDBASE");
std::string fname1 = rdbase + "/Code/GraphMol/MolTransforms/test_data/1oir.mol";
mol = MolFileToMol(fname1);
std::string fname2 = rdbase + "/Code/GraphMol/MolTransforms/test_data/1oir_canon.mol";
ROMol *mol2 = MolFileToMol(fname2);
Conformer &conf1 = mol->getConformer(0);
canonicalizeConformer(conf1);
Conformer &conf2 = mol2->getConformer();
unsigned int i, nats = mol->getNumAtoms();
for (i = 0; i < nats; ++i) {
CHECK_INVARIANT(comparePts(conf1.getAtomPos(i), conf2.getAtomPos(i)), "");
}
delete mol;
delete mol2;
}
void test1(){
std::cout << " ----------> Test1 "<< std::endl;
std::cout << " Finished <---------- "<< std::endl;
}
int main() {
//test1();
std::cout << "***********************************************************\n";
std::cout << "Testing MolTransforms\n";
std::cout << "\t---------------------------------\n";
std::cout << "\t test1Canonicalization \n\n";
test1Canonicalization();
std::cout << "***********************************************************\n";
return(0);
}
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