rdkit/Code/GraphMol/Descriptors/testATF.cpp

//  Created by Guillaume GODIN
//  Copyright (C) 2012-2020 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 <RDGeneral/test.h>
#include <RDGeneral/Invariant.h>
#include <GraphMol/RDKitBase.h>
#include <GraphMol/GraphMol.h>
#include <GraphMol/FileParsers/MolSupplier.h>
#include <GraphMol/FileParsers/MolWriters.h>
#include <GraphMol/SmilesParse/SmilesParse.h>
#include <RDGeneral/RDLog.h>
#include <vector>
#include <algorithm>
#include <fstream>
#include <sstream>

#include <chrono>  // for high_resolution_clock

#include <GraphMol/Descriptors/AtomFeat.h>

using namespace RDKit;

void test1() {
 
    auto m = "CO"_smiles; 

    TEST_ASSERT(m);
    
    std::vector<double> res;

    int atomid = 0;
    RDKit::Descriptors::AtomFeatVect(*m, res, atomid);

    std::vector <double > exp{ 0. , 1. , 0. , 0. , 0. , 0. , 0. , 0. , 0. , 0. , 0. , 0. , 0. ,
       0. , 0. , 1. , 0. , 0. , 0. , 0. , 0. , 0. , 0. , 1. , 0. , 0. ,
       0. , 0. , 0. , 1. , 0. , 0. , 0. , 0. , 1. , 0. , 0. , 0. , 0. ,
       0. , 0. , 0. , 0. , 0. , 0. , 0. , 1. , 0. , 0.5};

    // 49 features
    TEST_ASSERT(res.size() == 49);

    for (std::size_t i = 0; i < res.size() ; i++) {
     	TEST_ASSERT(fabs( res[i]-exp[i])< 0.001);
      //std::cout << res[i] << "," ;
    }


    
}

void test2() {
 
    auto m = "C1CC=C1[NH3+]"_smiles; 

    TEST_ASSERT(m);
    
    std::vector<double> res;

    std::vector <double > molatf{ 0,1,0,0,0,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,1,0,0,0,0,1,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0.2,
     0,1,0,0,0,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,1,0,0,0,0,1,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0.2,
     0,1,0,0,0,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,1,0,0,0,0,1,0,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,1,0,0,0,0.2,
     0,1,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,1,0,0,0,1,0,0,0,0,0,0,0,1,0,0,1,0,0,0,0,0,1,0,0,0,0,0.2,
     0,0,1,0,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,0,1,0,0.2};


    for (unsigned int j=0; j< m->getNumAtoms(); j++) {

      RDKit::Descriptors::AtomFeatVect(*m, res, j);

      // 49 features
      TEST_ASSERT(res.size() == 49);

      for (std::size_t i = 0; i < res.size() ; i++) {
        TEST_ASSERT(fabs( res[i]-molatf[i+j*49])< 0.001);
      }

     res.clear();
     res.resize(49);
    }
    
}

void test3() {
 
    auto m = "O[C@H](F)[C@H](F)O"_smiles; 

    TEST_ASSERT(m);

    std::vector <double > molatf{ 0,0,0,1,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,0,1,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0.166667,
    0,1,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0.166667,
    0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,1,0,0,0,0,0.166667,
    0,1,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0.166667,
    0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,1,0,0,0,0,0.166667,
    0,0,0,1,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,0,1,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0.166667};

    std::vector<double> res;

    for (unsigned int j=0; j< m->getNumAtoms(); j++) {

      RDKit::Descriptors::AtomFeatVect(*m, res, j);


      // 49 features
      TEST_ASSERT(res.size() == 49);

      for (std::size_t i = 0; i < res.size() ; i++) {
        TEST_ASSERT(fabs( res[i]-molatf[i+j*49])< 0.001);
      }

     res.clear();
     res.resize(49);
    }
}

void test4() {
 
    auto m = "O[C@H](F)[C@H](F)O"_smiles; 

    TEST_ASSERT(m);
    
    std::vector<double> res;

    std::vector <double > molatf{ 0,0,0,1,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,0,1,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0.166667,0,0,0,
    0,1,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0.166667,0,1,0,
    0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,1,0,0,0,0,0.166667,0,0,0,
    0,1,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0.166667,0,1,0,
    0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,1,0,0,0,0,0.166667,0,0,0,
    0,0,0,1,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,0,1,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0.166667,0,0,0};

    for (unsigned int j=0; j< m->getNumAtoms(); j++) {
      RDKit::Descriptors::AtomFeatVect(*m, res, j, true);

      // 52 features
      TEST_ASSERT(res.size() == 52);

      for (std::size_t i = 0; i < res.size() ; i++) {
        TEST_ASSERT(fabs( res[i]-molatf[i+j*52])< 0.001);
      }

     res.clear();
     res.resize(52);
    }
}

void test5() {
 
    auto m = "O[C@@H](F)[C@@H](F)O"_smiles; 

    TEST_ASSERT(m);
    
    std::vector<double> res;

    std::vector <double > molatf{ 0,0,0,1,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,0,1,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0.166667,0,0,0,
    0,1,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0.166667,1,0,0,
    0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,1,0,0,0,0,0.166667,0,0,0,
    0,1,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0.166667,1,0,0,
    0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,1,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,1,0,0,0,0,0.166667,0,0,0,
    0,0,0,1,0,0,0,0,0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,1,0,0,0,1,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0,1,0,0,0,0.166667,0,0,0};

    for (unsigned int j=0; j< m->getNumAtoms(); j++) {
      RDKit::Descriptors::AtomFeatVect(*m, res, j, true);

      // 52 features
      TEST_ASSERT(res.size() == 52);

      for (std::size_t i = 0; i < res.size() ; i++) {
        TEST_ASSERT(fabs( res[i]-molatf[i+j*52])< 0.001);
      }

     res.clear();
     res.resize(52);
    }
}

int main() {
  RDLog::InitLogs();
  test1();
  test2();
  test3();
  test4();
  test5();
}