1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 191 192 193 194 195 196 197 198 199 200 201 202 203 204 205 206 207 208 209 210 211 212 213 214 215 216 217 218 219 220 221 222 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 245 246 247 248 249 250 251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266 267 268 269 270 271 272 273 274 275 276 277 278 279 280 281 282 283 284 285 286 287 288 289 290 291 292 293 294 295 296 297 298 299 300 301 302 303 304 305
|
/****************************************************************************
* Copyright (C) 2009-2013 GGA Software Services LLC
*
* This file is part of Indigo toolkit.
*
* This file may be distributed and/or modified under the terms of the
* GNU General Public License version 3 as published by the Free Software
* Foundation and appearing in the file LICENSE.GPL included in the
* packaging of this file.
*
* This file is provided AS IS with NO WARRANTY OF ANY KIND, INCLUDING THE
* WARRANTY OF DESIGN, MERCHANTABILITY AND FITNESS FOR A PARTICULAR PURPOSE.
***************************************************************************/
#ifndef __molecule_tautomer_h__
#define __molecule_tautomer_h__
#include "base_cpp/array.h"
#include "base_cpp/tlscont.h"
#include "base_cpp/obj.h"
#include "graph/graph_decomposer.h"
#include "molecule/molecule.h"
#include "molecule/molecule_dearom.h"
#include "molecule/base_molecule.h"
#ifdef _WIN32
#pragma warning(push)
#pragma warning(disable:4251)
#endif
namespace indigo {
class Molecule;
class AromaticityMatcher;
class Dearomatizer;
class DearomatizationMatcher;
struct Atom;
//#define TRACE_TAUTOMER_MATCHING
struct TautomerRule
{
bool check (BaseMolecule &molecule, int first, int last, char other_arom_first, char other_arom_last) const;
Array<int> list1;
Array<int> list2;
int aromaticity1;
int aromaticity2;
static bool atomInAromaticRing (BaseMolecule &mol, int atom_idx);
};
struct TautomerSearchContext
{
explicit TautomerSearchContext (BaseMolecule &g1_, BaseMolecule &g2_, GraphDecomposer &decomposer1_, GraphDecomposer &decomposer2_,
const PtrArray<TautomerRule> &rules_list_, const AromaticityOptions &arom_options);
virtual ~TautomerSearchContext ();
BaseMolecule &g1;
BaseMolecule &g2;
GraphDecomposer &decomposer1;
GraphDecomposer &decomposer2;
// amount of metal bonds
CP_DECL;
TL_CP_DECL(Array<int>, h_rep_count_1);
TL_CP_DECL(Array<int>, h_rep_count_2);
const PtrArray<TautomerRule> &rules_list;
bool force_hydrogens;
bool ring_chain;
int rules;
bool substructure;
bool (*cb_check_rules) (TautomerSearchContext &context, int first1, int first2, int last1, int last2);
int max_chains;
AromaticityOptions arom_options;
TL_CP_DECL(DearomatizationsStorage, dearomatizations);
TL_CP_DECL(Array<int>, core_1);
TL_CP_DECL(Array<int>, core_2);
int initial_g1_vertexend;
TL_CP_DECL(Array<int>, chains_2);
TL_CP_DECL(Array<int>, edges_1);
TL_CP_DECL(Array<int>, edges_2);
TL_CP_DECL(Array<int>, edge_types_2);
TL_CP_DECL(Array<int>, n1);
TL_CP_DECL(Array<int>, n2);
Obj<Dearomatizer> dearomatizer;
Obj<DearomatizationMatcher> dearomatizationMatcher;
};
class TautomerMatcher
{
public:
explicit TautomerMatcher (TautomerSearchContext &context);
explicit TautomerMatcher (TautomerSearchContext &context, int start_path_number, int n_chains);
virtual ~TautomerMatcher ();
bool findMatch ();
void addPair (int n1, int n2, int arom_bond_idx2, int bond_type2);
bool nextPair (int &n1, int &n2, int &h_diff, int prev_n1, int prev_n2);
bool isFeasiblePair (int n1, int n2, int &h_diff);
void restore ();
static bool matchAtomsTau (BaseMolecule &g1, BaseMolecule &g2, int n1, int n2);
static bool matchBondsTau (Graph &subgraph, Graph &supergraph,
int sub_idx, int super_idx, void *userdata);
static bool matchBondsTauSub (Graph &subgraph, Graph &supergraph,
int sub_idx, int super_idx, void *userdata);
static bool fixBondsNotInChains (TautomerSearchContext &context, const int *core1, const int *core2);
private:
bool _checkInterPathBonds ();
static int _remainderEmbedding (Graph &g1, Graph &g2,
int *core1, int *core2, void *userdata);
static int _preliminaryEmbedding (Graph &g1, Graph &g2,
int *core1, int *core2, void *userdata);
static bool _matchAtoms (Graph &subgraph, Graph &supergraph,
const int *core_sub, int sub_idx, int super_idx, void *userdata);
static bool _matchAtomsEx (Graph &subgraph, Graph &supergraph,
const int *core_sub, int sub_idx, int super_idx, void *userdata);
struct MatchData
{
MatchData (TautomerSearchContext &context_) : context(context_) {}
TautomerSearchContext &context;
int start_path_number;
} _d;
int _n1;
int _n2;
int _bond_idx2;
int _n_chains;
};
class TautomerChainFinder
{
public:
explicit TautomerChainFinder (TautomerSearchContext &context, int h_difference,
int start_path_number, int n_chains);
explicit TautomerChainFinder (TautomerChainFinder &other);
virtual ~TautomerChainFinder ();
bool enumeratePaths ();
void addPair (int n1, int n2, bool is_zero_bond, int arom_bond_idx2, int bond_type2);
void restore ();
bool nextPair (int &n1, int &n2, int &e1, int &e2, int prev_e1, int prev_e2);
int isFeasiblePair (int n1, int n2, bool &zero_bond, int &arom_bond_idx2, int &bond_type2);
private:
TautomerSearchContext &_context;
int _prev_n1;
int _prev_n2;
int _bond_idx2;
int _path_length;
int _h_difference;
bool _is_zero_bond_present;
int _path_number;
int _start_idx1;
int _start_idx2;
int _n_chains;
};
class TautomerChainChecker
{
public:
explicit TautomerChainChecker (TautomerSearchContext &context,
const Array<int> &core1, const Array<int> &core2, int start_path_number);
explicit TautomerChainChecker (TautomerChainChecker &other);
virtual ~TautomerChainChecker ();
bool check ();
void addPair (int n1, int n2);
void restore();
bool nextStartingPair (int &n1, int &n2);
bool isFeasibleStartingPair (int n1, int n2, int &h_diff);
bool nextPair (int &n1, int &n2, int &e1, int &e2);
int isFeasiblePair (int n1, int n2, TautomerChainChecker &next1, TautomerChainChecker &next2);
bool releaseChain ();
void restoreChain ();
DECL_ERROR;
private:
bool _checkInterPathBonds ();
static bool _matchAromBonds (Graph &subgraph, Graph &supergraph,
int sub_idx, int super_idx, void *userdata);
static void _removeAtom (Graph &subgraph, int sub_idx, void *userdata);
static void _addBond (Graph &subgraph, Graph &supergraph,
int sub_idx, int super_idx, void *userdata);
static int _embedding (Graph &subgraph, Graph &supergraph,
int *core_sub, int *core_super, void *userdata);
bool _matchAromatizedQuery();
TautomerSearchContext &_context;
int _path_length;
int _h_difference;
// at the end of chain
int _final_path_length;
int _final_h_difference;
bool _is_zero_bond_present;
bool _is_query_bond_present;
bool _is_non_aromatic_bond_present;
int _path_number;
const Array<int> &_core_1;
const Array<int> &_core_2;
int _tau_bonds_to_match;
int _prev_n1;
int _prev_n2;
int _bond_idx1;
int _bond_idx2;
int _bond_type2;
int _start_idx1;
int _start_idx2;
};
class DLLEXPORT TautomerSuperStructure : public Molecule
{
public:
enum { NONE, TAUTOMER, ORIGINAL };
TautomerSuperStructure (Molecule &mol);
virtual ~TautomerSuperStructure ();
virtual void clear ();
virtual int getBondOrder (int idx);
virtual int getBondTopology (int idx);
virtual bool possibleBondOrder (int idx, int order);
virtual int getAtomTotalH (int idx);
bool isZeroedBond (int idx);
const int * getMapping ();
const Array<int> & getInvMapping ();
int getSubgraphType (const Array<int> &vertices, const Array<int> &edges);
protected:
void _findMinDistance (int source, int maxDist, Array<int> &dest, int *result);
void _collectAtomProperties (void);
void _getDoubleBondsCount (int i, int &double_count, int &arom_count);
bool _isAcceptingHeteroatom (int idx);
bool _isEmittingHeteroatom (int idx);
int _hetroatomsCount (int idx);
int _getBondOrder (int idx);
int _getBondTopology (int idx);
bool _inside_ctor;
CP_DECL;
TL_CP_DECL(Array<int>, _atomsEmitBond);
TL_CP_DECL(Array<int>, _atomsAcceptBond);
TL_CP_DECL(Array<bool>, _isBondAttachedArray);
TL_CP_DECL(Array<int>, _mapping);
TL_CP_DECL(Array<int>, _inv_mapping);
TL_CP_DECL(Array<int>, _edge_mapping);
TL_CP_DECL(Array<int>, _total_h);
};
}
#ifdef _WIN32
#pragma warning(pop)
#endif
#endif
|