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/************************************************************************
* obwrapper.cpp OpenBabel wrapper functions
*
* Copyright (c) 2004, 2018 by Ernst-G. Schmid
*
* This file is part of the xchem::tigress project.
*
* This program is free software; you can redistribute it and/or modify
* it under the terms of the GNU General Public License as published by
* the Free Software Foundation version 2 of the License.
*
* This program is distributed in the hope that it will be useful,
* but WITHOUT ANY WARRANTY; without even the implied warranty of
* MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
* lesser GNU General Public License for more details.
************************************************************************/
//#include <vector>
#if HAVE_SSTREAM
#include <sstream>
#elif HAVE_SSTREAM_H
#include <sstream.h>
#endif
#if HAVE_IOSTREAM
#include <iostream>
#elif HAVE_IOSTREAM_H
#include <iostream.h>
#endif
#include <iomanip>
#include <limits>
#include <mol.h>
#include <fingerprint.h>
#include <obconversion.h>
#include <openbabel/op.h>
#include <openbabel/query.h>
#include <openbabel/isomorphism.h>
#include <openbabel/groupcontrib.h>
#include <openbabel/spectrophore.h>
#include <openbabel/graphsym.h>
#include <openbabel/stereo/stereo.h>
#include <openbabel/stereo/tetrahedral.h>
#include <openbabel/stereo/cistrans.h>
#include <openbabel/stereo/squareplanar.h>
#include <obiter.h>
//#include <vf2/vf2.h>
#include "obwrapper.h"
using namespace OpenBabel;
using namespace std;
typedef struct
{
char type;
unsigned long atomids[2];
unsigned long refs[4];
OBStereo::Shape shape;
OBStereo::View view;
OBStereo::Winding winding;
} _STEREO;
//using namespace XchemTigress;
/*static const unsigned char popcount_counts_8[] =
{
0,1,1,2,1,2,2,3,1,2,2,3,2,3,3,4,1,2,2,3,2,3,3,4,2,3,3,4,3,4,4,5,
1,2,2,3,2,3,3,4,2,3,3,4,3,4,4,5,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,
1,2,2,3,2,3,3,4,2,3,3,4,3,4,4,5,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,
2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,
1,2,2,3,2,3,3,4,2,3,3,4,3,4,4,5,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,
2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,
2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,
3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8
};*/
static const unsigned char popcount_counts_16[] = {0,1,1,2,1,2,2,3,1,2,2,3,2,3,3,4,1,2,2,3,2,3,3,4,2,3,3,4,3,4,4,5,1,2,2,3,2,3,3,4,2,3,3,4,3,4,4,5,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,1,2,2,3,2,3,3,4,2,3,3,4,3,4,4,5,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,1,2,2,3,2,3,3,4,2,3,3,4,3,4,4,5,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,1,2,2,3,2,3,3,4,2,3,3,4,3,4,4,5,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,1,2,2,3,2,3,3,4,2,3,3,4,3,4,4,5,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,1,2,2,3,2,3,3,4,2,3,3,4,3,4,4,5,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,1,2,2,3,2,3,3,4,2,3,3,4,3,4,4,5,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,2,3,3,4,3,4,4,5,3,4,4,5,4,5,5,6,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,3,4,4,5,4,5,5,6,4,5,5,6,5,6,6,7,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,4,5,5,6,5,6,6,7,5,6,6,7,6,7,7,8,5,6,6,7,6,7,7,8,6,7,7,8,7,8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3,13,14,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,11,12,12,13,12,13,13,14,12,13,13,14,13,14,14,15,5,6,6,7,6,7,7,8,6,7,7,8,7,8,8,9,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,11,12,12,13,12,13,13,14,12,13,13,14,13,14,14,15,6,7,7,8,7,8,8,9,7,8,8,9,8,9,9,10,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,11,12,12,13,12,13,13,14,12,13,13,14,13,14,14,15,7,8,8,9,8,9,9,10,8,9,9,10,9,10,10,11,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,11,12,12,13,12,13,13,14,12,13,13,14,13,14,14,15,8,9,9,10,9,10,10,11,9,10,10,11,10,11,11,12,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,11,12,12,13,12,13,13,14,12,13,13,14,13,14,14,15,9,10,10,11,10,11,11,12,10,11,11,12,11,12,12,13,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,11,12,12,13,12,13,13,14,12,13,13,14,13,14,14,15,10,11,11,12,11,12,12,13,11,12,12,13,12,13,13,14,11,12,12,13,12,13,13,14,12,13,13,14,13,14,14,15,11,12,12,13,12,13,13,14,12,13,13,14,13,14,14,15,12,13,13,14,13,14,14,15,13,14,14,15,14,15,15,16};
//static bool ob_rehydrate_molecule(OBBase* pOb, char *serializedInput);
//static bool unserializeOBMol(OBBase* pOb, const char *serializedInput);
static inline bool unserializeOBMol(OpenBabel::OBBase* pOb, const char *serializedInput);
//static inline OBMol* convertToOBMol(const string input, const string format);
//static inline string convertFromOBMol(OBMol *input, const string format);
static inline OBMol* convertToOBMol(const string input, const string format)
{
OBMol *mol;
OBConversion conv;
istringstream molstream (input);
mol = new OBMol();
conv.SetInFormat(format.c_str());
conv.Read (mol, &molstream);
return mol;
}
static inline string convertFromOBMol(OBMol *input, const string format)
{
OBConversion conv;
ostringstream molstream;
conv.SetOutFormat(format.c_str());
conv.Write (input, &molstream);
return molstream.str();
}
extern "C" char *
ob_molfile_to_smiles (char *molfile, int omit_iso_and_chiral_markings)
{
OBMol mol;
OBConversion conv;
string tmpStr (molfile);
string outstring;
istringstream molstream (tmpStr);
ostringstream smilesstream;
char *tmpSmiles;
conv.SetInAndOutFormats ("MDL", "SMI");
conv.AddOption ("n", OBConversion::OUTOPTIONS);
if (omit_iso_and_chiral_markings != 0)
{
conv.AddOption ("i", OBConversion::OUTOPTIONS);
}
conv.Read (&mol, &molstream);
if (mol.Empty ())
return NULL;
conv.Write (&mol, &smilesstream);
outstring = smilesstream.str ();
//outstring = outstring.substr (0, outstring.length ()-1);
tmpSmiles = strdup (outstring.c_str ());
//printf("Orig: %s\n",tmpSmiles);
return (tmpSmiles);
}
extern "C" char *
ob_molfile_to_canonical_smiles (char *molfile, int omit_iso_and_chiral_markings)
{
OBMol mol;
OBConversion conv;
string tmpStr (molfile);
string outstring;
istringstream molstream (tmpStr);
ostringstream smilesstream;
char *tmpSmiles;
conv.SetInAndOutFormats ("MDL", "CAN");
conv.AddOption ("n", OBConversion::OUTOPTIONS);
//conv.AddOption ("c", OBConversion::OUTOPTIONS);
if (omit_iso_and_chiral_markings != 0)
{
conv.AddOption ("i", OBConversion::OUTOPTIONS);
}
conv.Read (&mol, &molstream);
if (mol.Empty ())
return NULL;
conv.Write (&mol, &smilesstream);
outstring = smilesstream.str ();
outstring = outstring.substr (0, outstring.length () - 1);
tmpSmiles = strdup (outstring.c_str ());
return (tmpSmiles);
}
extern "C" char *
ob_smiles_to_smiles (char *smiles, int omit_iso_and_chiral_markings)
{
OBMol mol;
OBConversion conv;
string tmpStr (smiles);
string outstring;
istringstream molstream (tmpStr);
ostringstream smilesstream;
char *tmpSmiles;
conv.SetInAndOutFormats ("SMI", "SMI");
conv.AddOption ("n", OBConversion::OUTOPTIONS);
if (omit_iso_and_chiral_markings != 0)
{
conv.AddOption ("i", OBConversion::OUTOPTIONS);
}
conv.Read (&mol, &molstream);
if (mol.Empty ())
return NULL;
conv.Write (&mol, &smilesstream);
outstring = smilesstream.str ();
//outstring = outstring.substr (0, outstring.length ()-1);
tmpSmiles = strdup (outstring.c_str ());
//printf("Orig: %s\n",tmpSmiles);
return (tmpSmiles);
}
extern "C" char *
ob_smiles_to_canonical_smiles (char *smiles, int omit_iso_and_chiral_markings)
{
OBMol mol;
OBConversion conv;
string tmpStr (smiles);
string outstring;
istringstream molstream (tmpStr);
ostringstream smilesstream;
char *tmpSmiles;
conv.SetInAndOutFormats ("SMI", "CAN");
conv.AddOption ("n", OBConversion::OUTOPTIONS);
//conv.AddOption ("c", OBConversion::OUTOPTIONS);
if (omit_iso_and_chiral_markings != 0)
{
conv.AddOption ("i", OBConversion::OUTOPTIONS);
}
conv.Read (&mol, &molstream);
if (mol.Empty ())
return NULL;
conv.Write (&mol, &smilesstream);
outstring = smilesstream.str ();
outstring = outstring.substr (0, outstring.length () - 1);
tmpSmiles = strdup (outstring.c_str ());
return (tmpSmiles);
}
extern "C" char *
ob_smiles_to_V2000 (char *smiles)
{
OBMol mol;
OBConversion conv;
//OBOp* pOp = OBOp::FindType("gen2D");
string tmpStr (smiles);
string outstring;
istringstream smilesstream (tmpStr);
ostringstream molstream;
char *tmpMolfile;
conv.SetInAndOutFormats ("SMI", "MDL");
conv.AddOption ("2", OBConversion::OUTOPTIONS);
conv.Read (&mol, &smilesstream);
if (mol.Empty ())
return NULL;
/*if(pOp)
pOp->Do(&mol);*/
conv.Write (&mol, &molstream);
outstring = molstream.str ();
// remove the trailling $$$$\n from the SDFile
if (outstring.find ("$$$$\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 5);
}
else if (outstring.find ("$$$$\r\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 6);
}
tmpMolfile = strdup (outstring.c_str ());
return (tmpMolfile);
}
extern "C" char *
ob_inchi_to_canonical_smiles (char *inchi, int omit_iso_and_chiral_markings)
{
OBMol mol;
OBConversion conv;
//OBOp* pOp = OBOp::FindType("gen2D");
string tmpStr (inchi);
string outstring;
istringstream inchistream (tmpStr);
ostringstream molstream;
char *tmpMolfile;
conv.SetInAndOutFormats ("INCHI", "CAN");
conv.AddOption ("n", OBConversion::OUTOPTIONS);
//conv.AddOption ("c", OBConversion::OUTOPTIONS);
if (omit_iso_and_chiral_markings != 0)
{
conv.AddOption ("i", OBConversion::OUTOPTIONS);
}
conv.Read (&mol, &inchistream);
if (mol.Empty ())
return NULL;
/*if(pOp)
pOp->Do(&mol);*/
conv.Write (&mol, &molstream);
outstring = molstream.str ();
// remove the trailling $$$$\n from the SDFile
if (outstring.find ("$$$$\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 5);
}
else if (outstring.find ("$$$$\r\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 6);
}
tmpMolfile = strdup (outstring.c_str ());
return (tmpMolfile);
}
extern "C" char *
ob_inchi_to_V2000 (char *inchi)
{
OBMol mol;
OBConversion conv;
//OBOp* pOp = OBOp::FindType("gen2D");
string tmpStr (inchi);
string outstring;
istringstream inchistream (tmpStr);
ostringstream molstream;
char *tmpMolfile;
conv.SetInAndOutFormats ("INCHI", "MDL");
conv.AddOption ("2", OBConversion::OUTOPTIONS);
conv.Read (&mol, &inchistream);
if (mol.Empty ())
return NULL;
/*if(pOp)
pOp->Do(&mol);*/
conv.Write (&mol, &molstream);
outstring = molstream.str ();
// remove the trailling $$$$\n from the SDFile
if (outstring.find ("$$$$\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 5);
}
else if (outstring.find ("$$$$\r\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 6);
}
tmpMolfile = strdup (outstring.c_str ());
return (tmpMolfile);
}
extern "C" char *
ob_molfile_to_V2000 (char *molfile)
{
OBMol mol;
OBConversion conv;
string tmpStr (molfile);
string outstring;
istringstream molstream (tmpStr);
ostringstream V2000stream;
char *tmpV2000;
conv.SetInAndOutFormats ("MDL", "MDL");
//conv.AddOption ("2", OBConversion::INOPTIONS);
conv.AddOption ("2", OBConversion::OUTOPTIONS);
conv.Read (&mol, &molstream);
if (mol.Empty ())
return NULL;
conv.Write (&mol, &V2000stream);
outstring = V2000stream.str ();
// remove the trailling $$$$\n from the SDFile
if (outstring.find ("$$$$\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 5);
}
else if (outstring.find ("$$$$\r\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 6);
}
tmpV2000 = strdup (outstring.c_str ());
return (tmpV2000);
}
extern "C" char *
ob_smiles_to_V3000 (char *smiles)
{
OBMol mol;
OBConversion conv;
string tmpStr (smiles);
string outstring;
istringstream molstream (tmpStr);
ostringstream V3000stream;
char *tmpV3000;
conv.SetInAndOutFormats ("SMI", "MDL");
//conv.AddOption ("2", OBConversion::INOPTIONS);
conv.AddOption ("3", OBConversion::OUTOPTIONS);
conv.Read (&mol, &molstream);
if (mol.Empty ())
return NULL;
conv.Write (&mol, &V3000stream);
outstring = V3000stream.str ();
// remove the trailling $$$$\n from the SDFile
if (outstring.find ("$$$$\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 5);
}
else if (outstring.find ("$$$$\r\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 6);
}
tmpV3000 = strdup (outstring.c_str ());
return (tmpV3000);
}
extern "C" char *
ob_V3000_to_V2000 (char *V3000)
{
OBMol mol;
OBConversion conv;
string tmpStr (V3000);
string outstring;
istringstream V3000stream (tmpStr);
ostringstream molstream;
char *tmpMolfile;
conv.SetInAndOutFormats ("MDL", "MDL");
conv.AddOption ("3", OBConversion::INOPTIONS);
conv.AddOption ("2", OBConversion::OUTOPTIONS);
conv.Read (&mol, &V3000stream);
conv.Write (&mol, &molstream);
outstring = molstream.str ();
// remove the trailling $$$$\n from the SDFile
if (outstring.find ("$$$$\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 5);
}
else if (outstring.find ("$$$$\r\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 6);
}
tmpMolfile = strdup (outstring.c_str ());
return (tmpMolfile);
}
extern "C" double
ob_molweight (char *smiles)
{
OBMol *mol;
string tmpStr (smiles);
double molweight = 0.0;
mol = convertToOBMol(tmpStr,"SMI");
molweight = mol->GetMolWt ();
delete mol;
return (molweight);
}
extern "C" char *
ob_hillformula (char *smiles)
{
string tmpStr (smiles);
string molfmla;
OBMol *mol;
char *tmpFormula;
mol = convertToOBMol(tmpStr,"SMI");
molfmla = mol->GetFormula ();
delete mol;
tmpFormula = strdup (molfmla.c_str ());
return (tmpFormula);
}
extern "C" unsigned int
ob_num_atoms (char *smiles)
{
OBMol *mol;
string tmpStr (smiles);
unsigned int numatoms = 0;
mol = convertToOBMol(tmpStr,"SMI");
//mol.AddHydrogens (false, false);
numatoms = mol->NumAtoms ();
delete mol;
return (numatoms);
}
extern "C" unsigned int
ob_num_heavy_atoms (char *smiles)
{
OBMol *mol;
string tmpStr (smiles);
unsigned int numheavyatoms = 0;
mol = convertToOBMol(tmpStr,"SMI");
numheavyatoms = mol->NumHvyAtoms ();
delete mol;
return (numheavyatoms);
}
extern "C" unsigned int
ob_num_bonds (char *smiles)
{
OBMol *mol;
string tmpStr (smiles);
unsigned int numbonds = 0;
mol = convertToOBMol(tmpStr,"SMI");
//mol.AddHydrogens (false, false);
numbonds = mol->NumBonds ();
delete mol;
return (numbonds);
}
extern "C" unsigned int
ob_num_rotatable_bonds (char *smiles)
{
OBMol *mol;
string tmpStr (smiles);
unsigned int numrotors = 0;
mol = convertToOBMol(tmpStr,"SMI");
numrotors = mol->NumRotors ();
delete mol;
return (numrotors);
}
extern "C" int
ob_total_charge (char *smiles)
{
OBMol *mol;
string tmpStr (smiles);
int totalcharge = 0;
mol = convertToOBMol(tmpStr,"SMI");
totalcharge = mol->GetTotalCharge ();
delete mol;
return (totalcharge);
}
extern "C" unsigned int
ob_is_nostruct (char *molfile)
{
OBMol *mol;
string tmpStr (molfile);
bool empty = false;
mol = convertToOBMol(tmpStr,"MDL");
empty = mol->Empty();
delete mol;
return empty ? 1 : 0;
}
extern "C" unsigned int
ob_is_chiral (char *smiles)
{
OBMol *mol;
string tmpStr (smiles);
bool chiral = false;
mol = convertToOBMol(tmpStr,"SMI");
mol->FindChiralCenters();
chiral = mol->IsChiral();
delete mol;
return chiral ? 1 : 0;
}
extern "C" int
ob_2D (char *molfile)
{
OBMol *mol;
string tmpStr (molfile);
bool twod = false;
mol = convertToOBMol(tmpStr,"MDL");
twod = mol->Has2D();
delete mol;
return twod ? 1 : 0;
}
extern "C" int
ob_3D (char *molfile)
{
OBMol *mol;
string tmpStr (molfile);
bool threed = false;
mol = convertToOBMol(tmpStr,"MDL");
threed = mol->Has3D();
delete mol;
return threed ? 1 : 0;
}
extern "C" char *
ob_add_hydrogens (char *smiles, int polaronly, int correct4PH, double PH)
{
OBMol *mol;
string tmpStr (smiles);
string outstring;
char *tmpMolfile;
mol = convertToOBMol(tmpStr, "SMI");
mol->AddHydrogens((polaronly != 0), (correct4PH != 0), PH);
outstring = convertFromOBMol(mol,"SMI");
delete mol;
// remove the trailling $$$$\n from the SDFile
if (outstring.find ("$$$$\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 5);
}
else if (outstring.find ("$$$$\r\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 6);
}
tmpMolfile = strdup (outstring.c_str());
return tmpMolfile;
}
extern "C" char *
ob_delete_hydrogens (char *smiles, int nonpolaronly)
{
OBMol *mol;
string tmpStr (smiles);
string outstring;
char *tmpMolfile;
mol = convertToOBMol(tmpStr, "SMI");
if(mol->NumHvyAtoms () > 0)
{
if (nonpolaronly != 0)
{
mol->DeleteNonPolarHydrogens ();
}
else
{
mol->DeleteHydrogens ();
}
}
else
{
cout << "Warning: Cannot remove hydrogens. Resulting molecule would be empty!" << endl;
}
outstring = convertFromOBMol(mol,"SMI");
delete mol;
// remove the trailling $$$$\n from the SDFile
if (outstring.find ("$$$$\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 5);
}
else if (outstring.find ("$$$$\r\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 6);
}
tmpMolfile = strdup (outstring.c_str ());
return tmpMolfile;
}
extern "C" char *
ob_strip_salts (char *smiles, int neutralize_residue)
{
OBAtom atom;
OBMol *mol;
string tmpStr (smiles);
string outstring;
char *tmpMolfile;
mol = convertToOBMol(tmpStr, "SMI");
mol->StripSalts(0);
if(neutralize_residue != 0)
{
mol->ConvertDativeBonds();
FOR_ATOMS_OF_MOL(atom, mol)
{
atom->SetFormalCharge(0);
}
}
outstring = convertFromOBMol(mol,"SMI");
delete mol;
// remove the trailling $$$$\n from the SDFile
if (outstring.find ("$$$$\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 5);
}
else if (outstring.find ("$$$$\r\n", 0) != string::npos)
{
outstring = outstring.substr (0, outstring.length () - 6);
}
tmpMolfile = strdup (outstring.c_str ());
return tmpMolfile;
}
extern "C" double
ob_exactmass (char *smiles)
{
OBMol *mol;
string tmpStr (smiles);
double exactmass = 0.0;
mol = convertToOBMol(tmpStr, "SMI");
exactmass = mol->GetExactMass();
delete mol;
return exactmass;
}
extern "C" char*
ob_describe_fp2 (char *smiles)
{
OBMol *mol;
OBFingerprint *fprint=NULL;
string tmpStr (smiles);
//string fp_mode ("FP2");
vector < unsigned int >vfp;
fprint = OBFingerprint::FindFingerprint ("FP2");
vector < unsigned int >::iterator i;
string desc;
char* description=NULL;
//memset(fp,0x0, FPSIZE2*sizeof(unsigned int));
mol = convertToOBMol(tmpStr, "SMI");
mol->ConvertDativeBonds();
fprint->GetFingerprint (mol, vfp);
desc = fprint->DescribeBits(vfp);
description = strdup(desc.c_str());
delete mol;
/* for (i = vfp.begin();i != vfp.end();i++) {
fp[j++]=*i;
}*/
//memcpy (fp, &vfp[0], FPSIZE2*sizeof(unsigned int));
//delete fprint;
return description;
}
extern "C" void
ob_fp3 (char *smiles, unsigned int *fp)
{
OBMol *mol;
OBFingerprint *fprint=NULL;
string tmpStr (smiles);
//string fp_mode ("evoFP");
//string fp_mode ("FPPC8");
vector < unsigned int >vfp;
fprint = OBFingerprint::FindFingerprint ("FPPC8");
//vector < unsigned int >::iterator i;
int len=0;
memset(fp,0x0, OB_FPSIZE3*sizeof(unsigned int));
if (fprint != NULL)
{
mol = convertToOBMol(tmpStr, "SMI");
mol->ConvertDativeBonds();
fprint->GetFingerprint (mol, vfp);
delete mol;
/* for (i = vfp.begin();i != vfp.end();i++) {
fp[j++]=*i;
printf("%i",*i);
}*/
len = vfp.size();
//cout << len << endl;
if (len > OB_FPSIZE3)
{
len = OB_FPSIZE3;
cout << "Warning: Index dictionary size exceeded. Only the first " << OB_FPSIZE3*sizeof(unsigned int)*8 << " bits will be used!" << endl;
}
memcpy (fp, &vfp[0], len*sizeof(unsigned int));
}
else
{
cout << "FPPC8 fingerprint not found!" << endl;
}
}
extern "C" void
ob_fp_ECFP_n (char *smiles, unsigned int *fp, unsigned int type, unsigned int len)
{
OBMol *mol;
OBFingerprint *fprint=NULL;
string tmpStr (smiles);
vector < unsigned int >vfp;
switch (type)
{
case 0:
fprint = OBFingerprint::FindFingerprint ("ECFP0");
break;
case 2:
fprint = OBFingerprint::FindFingerprint ("ECFP2");
break;
case 4:
fprint = OBFingerprint::FindFingerprint ("ECFP4");
break;
case 6:
fprint = OBFingerprint::FindFingerprint ("ECFP6");
break;
case 8:
fprint = OBFingerprint::FindFingerprint ("ECFP8");
break;
case 10:
fprint = OBFingerprint::FindFingerprint ("ECFP10");
break;
}
memset(fp,0x0, len);
if (fprint != NULL)
{
mol = convertToOBMol(tmpStr,"SMI");
mol->ConvertDativeBonds();
fprint->GetFingerprint (mol, vfp, len * 8);
delete mol;
memcpy (fp, &vfp[0], len);
}
else
{
cout << "ECFP " << type << " fingerprint not found!" << endl;
}
}
extern "C" void
ob_fp_MACCS (char *smiles, unsigned int *fp)
{
OBMol *mol;
OBFingerprint *fprint=NULL;
string tmpStr (smiles);
//string fp_mode ("evoFP");
//string fp_mode ("FPPC8");
vector < unsigned int >vfp;
fprint = OBFingerprint::FindFingerprint ("MACCS");
//vector < unsigned int >::iterator i;
int len=0;
memset(fp,0x0, OB_FPSIZE_MACCS*sizeof(unsigned int));
if (fprint != NULL)
{
mol = convertToOBMol(tmpStr,"SMI");
mol->ConvertDativeBonds();
//cout << mol.NumHvyAtoms() << endl;
//cout << fprint->GetID() << endl;
fprint->GetFingerprint (mol, vfp);
delete mol;
/* for (i = vfp.begin();i != vfp.end();i++) {
fp[j++]=*i;
printf("%i",*i);
} */
len = vfp.size();
//cout << len << endl;
if (len > OB_FPSIZE_MACCS)
{
len = OB_FPSIZE_MACCS;
cout << "Warning: Index dictionary size exceeded. Only the first " << OB_FPSIZE_MACCS*sizeof(unsigned int)*8 << " bits will be used!" << endl;
}
memcpy (fp, &vfp[0], len*sizeof(unsigned int));
}
else
{
cout << "MACCS fingerprint not found!" << endl;
}
}
extern "C" void
ob_fp (char *smiles, unsigned int *fp)
{
OBMol *mol;
OBFingerprint *fprint2, *fprint3;
vector < unsigned int >vfp;
fprint2 = OBFingerprint::FindFingerprint ("FP2");
fprint3 = OBFingerprint::FindFingerprint ("FPPC8");
vector < unsigned int >::iterator i;
string tmpStr (smiles);
int len;
//ob_rehydrate_molecule(&mol, serializedInput);
mol = convertToOBMol(tmpStr,"SMI");
mol->ConvertDativeBonds();
fprint2->GetFingerprint (mol, vfp);
memset(fp,0x0, OB_FPSIZE*sizeof(unsigned int));
memcpy (fp, &vfp[0], OB_FPSIZE2*sizeof(unsigned int));
if (fprint3 != NULL)
{
vfp.clear();
fprint3->GetFingerprint (mol, vfp);
len = vfp.size();
if (len > OB_FPSIZE3)
{
len = OB_FPSIZE3;
cout << "Warning: Index dictionary size exceeded. Only the first " << OB_FPSIZE3*sizeof(unsigned int)*8 << " bits will be used!" << endl;
}
memcpy (fp+OB_OFFSET, &vfp[0], len*sizeof(unsigned int));
}
else
{
cout << "FPPC8 fingerprint not found!" << endl;
}
delete mol;
}
extern "C" double
ob_tanimoto (const unsigned int *fp1, const unsigned int *fp2, unsigned short size)
{
// Fast tanimoto code with 16 bit LUT by Andrew Dalke as published in http://www.dalkescientific.com/writings/diary/archive/2008/06/27/computing_tanimoto_scores.html.
// Used with permission
unsigned int and_count=0, or_count=0,t;
while (size--)
{
t = (*fp2 | *fp1);
or_count += popcount_counts_16[t&65535];
or_count += popcount_counts_16[t>>16];
t = (*fp2 & *fp1);
and_count += popcount_counts_16[t&65535];
and_count += popcount_counts_16[t>>16];
fp2++;
fp1++;
}
return static_cast<double>(and_count)/or_count;
}
extern "C" double
ob_tversky (const unsigned int *fp1_prototype, const unsigned int *fp2_variant, unsigned short size, double alpha_prototype, double beta_variant)
{
unsigned int a=0,b=0,c=0,t;
if(alpha_prototype<0.0f) alpha_prototype=0.0f;
if(alpha_prototype>1.0f) alpha_prototype=1.0f;
if(beta_variant<0.0f) beta_variant=0.0f;
if(beta_variant>1.0f) beta_variant=1.0f;
while (size--)
{
t = (*fp2_variant & *fp1_prototype);
a += popcount_counts_16[(*fp1_prototype)&65535];
a += popcount_counts_16[(*fp1_prototype)>>16];
b += popcount_counts_16[(*fp2_variant)&65535];
b += popcount_counts_16[(*fp2_variant)>>16];
c += popcount_counts_16[t&65535];
c += popcount_counts_16[t>>16];
fp1_prototype++;
fp2_variant++;
}
return static_cast<double>(c)/((a - c)*alpha_prototype+(b - c)*beta_variant+c);
}
extern "C" unsigned int
ob_popcount (const unsigned char *fp, unsigned short size)
{
unsigned int popcount=0, i;
for (i=0; i<size; i++)
{
popcount += popcount_counts_16[fp[i]];
}
return popcount;
}
/* Copyright © The International Union of Pure and Applied Chemistry 2005: IUPAC
International Chemical Identifier (InChI) (contact: secretariat@iupac.org) */
extern "C" char *
ob_smiles_to_inchi (char *smiles)
{
OBMol *mol;
OBConversion conv;
string tmpStr (smiles);
string outstring;
ostringstream inchistream;
char *tmpInChI;
conv.SetOutFormat ("INCHI");
conv.AddOption ("w", OBConversion::OUTOPTIONS);
mol = convertToOBMol(tmpStr,"SMI");
conv.Write (mol, &inchistream);
delete mol;
//cout << inchistream.str();
outstring = inchistream.str ();
outstring = outstring.substr (0, outstring.length () - 1);
tmpInChI = strdup (outstring.c_str ());
return tmpInChI;
}
extern "C" char *
ob_smiles_to_inchikey (char *smiles)
{
OBMol *mol;
OBConversion conv;
string tmpStr (smiles);
string outstring;
ostringstream inchikeystream;
char *tmpInChIkey;
conv.SetOutFormat("INCHI");
conv.AddOption ("w", OBConversion::OUTOPTIONS);
conv.AddOption ("K", OBConversion::OUTOPTIONS);
mol = convertToOBMol(tmpStr,"SMI");
conv.Write (mol, &inchikeystream);
delete mol;
//cout << inchistream.str();
outstring = inchikeystream.str ();
outstring = outstring.substr (0, outstring.length () - 1);
tmpInChIkey = strdup (outstring.c_str());
return (tmpInChIkey);
}
extern "C" char *
ob_molfile_to_inchikey (char *molfile)
{
OBMol *mol;
OBConversion conv;
string tmpStr (molfile);
string outstring;
ostringstream inchikeystream;
char *tmpInChIkey;
conv.SetOutFormat("INCHI");
conv.AddOption ("w", OBConversion::OUTOPTIONS);
conv.AddOption ("K", OBConversion::OUTOPTIONS);
mol = convertToOBMol(tmpStr,"MDL");
conv.Write (mol, &inchikeystream);
delete mol;
//cout << inchistream.str();
outstring = inchikeystream.str ();
outstring = outstring.substr (0, outstring.length () - 1);
tmpInChIkey = strdup (outstring.c_str ());
return (tmpInChIkey);
}
extern "C" char *
ob_spectrophore (char *smiles)
{
OBMol *mol;
OBConversion conv;
OBSpectrophore spec;
string tmpStr (smiles);
stringstream outstringstream;
vector<double> sphorevec;
int len=0;
mol = convertToOBMol(tmpStr,"SMI");
/*spec.SetResolution(3.0);
spec.SetAccuracy(spec.AccuracyOption::AngStepSize20);
spec.SetStereo(NoStereoSpecificProbes);
spec.SetNormalization(NormalizationTowardsZeroMean);*/
sphorevec = spec.GetSpectrophore(mol);
delete mol;
outstringstream << setprecision(16);
len = sphorevec.size();
for(int i(0); i<len; i++)
{
outstringstream << sphorevec[i];
if(i<len-1) outstringstream << ";";
}
return strdup(outstringstream.str().c_str());
}
extern "C" int
ob_SSS_SMARTS_native (const char *smarts_pattern, char *smiles)
{
OBMol *mol;
OBSmartsPattern sp;
string tmpStr (smiles);
bool match = false;
if (!sp.Init (smarts_pattern)) return -1;
mol = convertToOBMol(tmpStr,"SMI");
if (!mol->Empty ())
{
//if(mol.NumHvyAtoms() < sp.NumAtoms()) return 0;
match = sp.Match (*mol,true);
}
delete mol;
//maplist = sp.GetUMapList ();
//return maplist.size ();
return match ? 1 : 0;
}
extern "C" int
ob_SSS (const char *query_smiles, const char *target_smiles)
{
OBMol *mol_target;
OBQuery *query;
OBIsomorphismMapper *mapper;
OBIsomorphismMapper::Mapping mapping;
//string mol_query_string(query_molfile);
string mol_target_string(target_smiles);
bool match = false;
//mol_target = convertToOBMol(mol_target_string,"MOL");
mol_target = convertToOBMol(mol_target_string,"SMI");
if (mol_target->Empty())
{
}
else
{
query = CompileSmilesQuery(query_smiles);
mapper = OBIsomorphismMapper::GetInstance(query,"VF2");
mapper->MapFirst(mol_target, mapping);
match = (mapping.size()!=0);
}
//delete mol_query;
delete mol_target;
return match ? 1 : 0;
}
extern "C" int
ob_SSS_count (const char *query_smiles, const char *target_smiles)
{
OBMol *mol_target;
OBQuery *query;
OBIsomorphismMapper *mapper;
OBIsomorphismMapper::Mappings mappings;
//string mol_query_string(query_molfile);
string mol_target_string(target_smiles);
int matchcount = -1;
//mol_query = convertToOBMol(mol_query_string,"MOL");
mol_target = convertToOBMol(mol_target_string,"SMI");
if (mol_target->Empty())
{
}
else
{
query = CompileSmilesQuery(query_smiles);
mapper = OBIsomorphismMapper::GetInstance(query,"VF2");
mapper->MapUnique(mol_target, mappings);
matchcount = mappings.size();
}
//delete mol_query;
delete mol_target;
return matchcount;
}
extern "C" int
ob_SSS_SMARTS_native_count (const char *smarts_pattern, char *smiles)
{
OBMol *mol;
OBSmartsPattern sp;
string tmpStr (smiles);
//vector <vector<int> > maplist;
int matchcount = 0;
if(!sp.Init (smarts_pattern)) return -1;
mol = convertToOBMol(tmpStr,"SMI");
if (!mol->Empty ())
{
//if(mol.NumHvyAtoms() < sp.NumAtoms()) return 0;
if (sp.Match(*mol,false))
{
matchcount = sp.GetUMapList().size();
//matchcount=sp.NumMatches();
}
}
delete mol;
//maplist = sp.GetUMapList ();
//return maplist.size ();
return matchcount;
}
extern "C" double
ob_MR (char *smiles)
{
OBMol *mol;
//OBMR mr; //2.1.1
//OBGroupContrib theMR("MR", "mr.txt", "molar refractivity");
OBDescriptor* pDescr = OBDescriptor::FindType("MR");
string tmpStr (smiles);
double MR = 0.0;
mol = convertToOBMol(tmpStr,"SMI");
mol->AddHydrogens (false, false);
//MR = mr.Predict (mol);
if(pDescr)
MR = pDescr->Predict(mol);
delete mol;
return (MR);
}
extern "C" double
ob_TPSA (char *smiles)
{
OBMol *mol;
// //OBPSA psa; //2.1.1
//OBGroupContrib theTPSA("TPSA", "psa.txt", "topological polar surface area");
OBDescriptor* pDescr = OBDescriptor::FindType("TPSA");
string tmpStr (smiles);
double TPSA = 0.0;
mol = convertToOBMol(tmpStr,"SMI");
//
mol->AddHydrogens (false, false);
//
// //PSA = psa.Predict (mol);
if(pDescr)
TPSA = pDescr->Predict(mol);
delete mol;
return (TPSA);
}
extern "C" double
ob_logP (char *smiles)
{
OBMol *mol;
//OBLogP theLOGP; //2.1.1
//OBGroupContrib thelogP("logP", "logp.txt", "octanol/water partition coefficient");
OBDescriptor* pDescr = OBDescriptor::FindType("logP");
string tmpStr (smiles);
double LOGP = 0.0;
mol = convertToOBMol(tmpStr,"SMI");
mol->AddHydrogens (false, false);
//
//LOGP = theLOGP.Predict (mol);
if(pDescr)
LOGP = pDescr->Predict(mol);
delete mol;
return (LOGP);
}
extern "C" unsigned int
ob_num_H_donors (char *smiles)
{
OBMol *mol;
string tmpStr (smiles);
unsigned int numHdonors = 0;
mol = convertToOBMol(tmpStr,"SMI");
FOR_ATOMS_OF_MOL(a, mol)
{
if(a->IsHbondDonor()) numHdonors++;
}
delete mol;
return (numHdonors);
}
extern "C" unsigned int
ob_num_H_acceptors (char *smiles)
{
OBMol *mol;
string tmpStr (smiles);
unsigned int numHacceptors = 0;
mol = convertToOBMol(tmpStr,"SMI");
FOR_ATOMS_OF_MOL(a, mol)
{
if(a->IsHbondAcceptor()) numHacceptors++;
}
delete mol;
return (numHacceptors);
}
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