rdkit/Code/GraphMol/ReducedGraphs/test1.cpp

// $Id$
//
//  Copyright (C) 2013 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/RDKitBase.h>
#include <GraphMol/SmilesParse/SmilesParse.h>
#include <GraphMol/SmilesParse/SmilesWrite.h>
#include <GraphMol/ReducedGraphs/ReducedGraphs.h>
#include <DataStructs/ExplicitBitVect.h>

#include <RDGeneral/RDLog.h>
#include <string>

using namespace RDKit;

void test1(){
  BOOST_LOG(rdInfoLog) <<"testing basics" << std::endl;
  {
    std::string smi = "c1ccccc1CCO";
    ROMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    
    RDNumeric::DoubleVector *fp=ReducedGraphs::getErGFingerprint(*m1);
    std::cerr<<*fp<<std::endl;
    
    delete fp;
    delete m1;
  }

  {
    std::string smi = "c1cnccc1CCO";
    ROMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    
    RDNumeric::DoubleVector *fp=ReducedGraphs::getErGFingerprint(*m1);
    std::cerr<<*fp<<std::endl;
    
    delete fp;
    delete m1;
  }

  {
    std::string smi = "OCCC1=CC2=C(C=CC=C2)C=C1";
    ROMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    
    RDNumeric::DoubleVector *fp=ReducedGraphs::getErGFingerprint(*m1);
    std::cerr<<*fp<<std::endl;
    
    delete fp;
    delete m1;
  }

  {
    std::string smi = "OCCC1=CC2=C(C=CC=C2)N=C1";
    ROMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    
    RDNumeric::DoubleVector *fp=ReducedGraphs::getErGFingerprint(*m1);
    std::cerr<<*fp<<std::endl;
    
    delete fp;
    delete m1;
  }
  {
    std::string smi = "OCCC1=CC2=C(CCCC2)N=C1";
    ROMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    
    RDNumeric::DoubleVector *fp=ReducedGraphs::getErGFingerprint(*m1);
    std::cerr<<*fp<<std::endl;
    
    delete fp;
    delete m1;
  }
  {
    std::string smi = "OCCc1ccc(CC(C)C)cc1";
    ROMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    
    RDNumeric::DoubleVector *fp=ReducedGraphs::getErGFingerprint(*m1);
    std::cerr<<*fp<<std::endl;
    
    delete fp;
    delete m1;
  }
  {
    std::string smi = "OCCC1CCC(CC(C)C)CC1";
    ROMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    
    RDNumeric::DoubleVector *fp=ReducedGraphs::getErGFingerprint(*m1);
    std::cerr<<*fp<<std::endl;
    
    delete fp;
    delete m1;
  }
  {
    std::string smi = "OCCC1=CCC(CC(C)C)CC1";
    ROMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    
    RDNumeric::DoubleVector *fp=ReducedGraphs::getErGFingerprint(*m1);
    std::cerr<<*fp<<std::endl;
    
    delete fp;
    delete m1;
  }
  {
    std::string smi = "OCCC1=CCC(CC(C)C)C=C1";
    ROMol *m1 = SmilesToMol(smi);
    TEST_ASSERT(m1);
    
    RDNumeric::DoubleVector *fp=ReducedGraphs::getErGFingerprint(*m1);
    std::cerr<<*fp<<std::endl;
    
    delete fp;
    delete m1;
  }
  
  BOOST_LOG(rdInfoLog) <<"done" << std::endl;
}


void test2(){
  BOOST_LOG(rdInfoLog) <<"testing basics2" << std::endl;
  {
    std::string smi1 = "c1ccccc1CCO";
    std::string smi2 = "C1=CC=CCC1CCO";
    ROMol *m1 = SmilesToMol(smi1);
    TEST_ASSERT(m1);
    ROMol *m2 = SmilesToMol(smi2);
    TEST_ASSERT(m2);
    
    RDNumeric::DoubleVector *fp1=ReducedGraphs::getErGFingerprint(*m1);
    RDNumeric::DoubleVector *fp2=ReducedGraphs::getErGFingerprint(*m2);

    TEST_ASSERT(feq(RDNumeric::TanimotoSimilarity(*fp1,*fp2),1.0,0.001));
    
    delete fp1;
    delete fp2;
    delete m1;
    delete m2;
  }
  {
    std::string smi1 = "c1ccccc1CCO";
    std::string smi2 = "C1CC=CCC1CCO";
    ROMol *m1 = SmilesToMol(smi1);
    TEST_ASSERT(m1);
    ROMol *m2 = SmilesToMol(smi2);
    TEST_ASSERT(m2);
    
    RDNumeric::DoubleVector *fp1=ReducedGraphs::getErGFingerprint(*m1);
    RDNumeric::DoubleVector *fp2=ReducedGraphs::getErGFingerprint(*m2);

    TEST_ASSERT(!feq(RDNumeric::TanimotoSimilarity(*fp1,*fp2),1.0,0.001));
    
    delete fp1;
    delete fp2;
    delete m1;
    delete m2;
  }

  BOOST_LOG(rdInfoLog) <<"done" << std::endl;
}

int main(int argc,char *argv[]){
  RDLog::InitLogs();
  test1();
  test2();
  return 0;
}