File: node.cpp

package info (click to toggle)
rdkit 202503.6-3
  • links: PTS, VCS
  • area: main
  • in suites: forky, sid
  • size: 222,000 kB
  • sloc: cpp: 411,111; python: 78,482; ansic: 26,181; java: 8,285; javascript: 4,404; sql: 2,393; yacc: 1,626; lex: 1,267; cs: 1,090; makefile: 581; xml: 229; fortran: 183; sh: 121
file content (323 lines) | stat: -rw-r--r-- 10,981 bytes parent folder | download
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
306
307
308
309
310
311
312
313
314
315
316
317
318
319
320
321
322
323
//
//  Copyright (c) 2024, Glysade Inc
//  All rights reserved.
//
// Redistribution and use in source and binary forms, with or without
// modification, are permitted provided that the following conditions are
// met:
//
//     * Redistributions of source code must retain the above copyright
//       notice, this list of conditions and the following disclaimer.
//     * Redistributions in binary form must reproduce the above
//       copyright notice, this list of conditions and the following
//       disclaimer in the documentation and/or other materials provided
//       with the distribution.
//     * Neither the name of Novartis Institutes for BioMedical Research Inc.
//       nor the names of its contributors may be used to endorse or promote
//       products derived from this software without specific prior written
//       permission.
//
// THIS SOFTWARE IS PROVIDED BY THE COPYRIGHT HOLDERS AND CONTRIBUTORS
// "AS IS" AND ANY EXPRESS OR IMPLIED WARRANTIES, INCLUDING, BUT NOT
// LIMITED TO, THE IMPLIED WARRANTIES OF MERCHANTABILITY AND FITNESS FOR
// A PARTICULAR PURPOSE ARE DISCLAIMED. IN NO EVENT SHALL THE COPYRIGHT
// OWNER OR CONTRIBUTORS BE LIABLE FOR ANY DIRECT, INDIRECT, INCIDENTAL,
// SPECIAL, EXEMPLARY, OR CONSEQUENTIAL DAMAGES (INCLUDING, BUT NOT
// LIMITED TO, PROCUREMENT OF SUBSTITUTE GOODS OR SERVICES; LOSS OF USE,
// DATA, OR PROFITS; OR BUSINESS INTERRUPTION) HOWEVER CAUSED AND ON ANY
// THEORY OF LIABILITY, WHETHER IN CONTRACT, STRICT LIABILITY, OR TORT
// (INCLUDING NEGLIGENCE OR OTHERWISE) ARISING IN ANY WAY OUT OF THE USE
// OF THIS SOFTWARE, EVEN IF ADVISED OF THE POSSIBILITY OF SUCH DAMAGE.
//#include "node.h"
#include "fragment.h"
#include "utils.h"

namespace RDKit {
namespace ChemDraw {
bool parseNode(
    RWMol &mol, unsigned int fragmentId, CDXNode &node, PageData &pagedata,
    std::map<std::pair<int, StereoGroupType>, StereoGroupInfo> &sgroups,
    int &missingFragId, int externalAttachment) {
  int atom_id = node.GetObjectID();
  int elemno = node.m_elementNum;  // default to carbon
  // UINT16 max is not addigned?
  int num_hydrogens =
      node.m_numHydrogens == kNumHydrogenUnspecified ? 0 : node.m_numHydrogens;
  bool explicitHs = node.m_numHydrogens != kNumHydrogenUnspecified;
  int charge = 0;
  if ((node.m_charge & 0x00FFFFFF) == 0)
    charge = node.m_charge >> 24;
  else
    charge = node.m_charge;
  int atommap = 0;
  int rgroup_num = -1;
  int isotope = node.m_isotope;

  bool checkForRGroup = false;
  ;
  std::string query_label;
  std::vector<int16_t> elementlist;

  // position node.m_2dPosition;
#ifdef DEBUG
  std::cerr << NodeType(node.m_nodeType) << std::endl;
#endif
  switch (node.m_nodeType) {
    case kCDXNodeType_Element: {
      break;
    }
    case kCDXNodeType_ElementList: {
      if (node.m_elementList) {
        elementlist = *node.m_elementList;
        query_label = "ElementList";
      }
      break;
    }
    case kCDXNodeType_Nickname: {
      elemno = 0;
      atommap = atom_id;
      break;
    }
    case kCDXNodeType_Fragment: {
      elemno = 0;
      atommap = atom_id;
      break;
    }
    case kCDXNodeType_ExternalConnectionPoint: {
      if (externalAttachment <= 0) {
        // sometimes this is a dummy atom, but I don't know when.
        if (node.m_externalConnectionType == kCDXExternalConnection_Diamond) {
          elemno = 0;
        }
        atommap = atom_id;
      } else {
        elemno = 0;
        atommap = externalAttachment;
      }
      break;
    }
    case kCDXNodeType_GenericNickname: {
      if (node.m_genericNickname.size()) {
        switch (node.m_genericNickname[0]) {
          case 'R': {
            checkForRGroup = true;
            elemno = 0;
            query_label = node.m_genericNickname;
            break;
          }
          case 'A':
          case 'Q':
          case 'X':
          case 'M': {
            elemno = 0;
            query_label = node.m_genericNickname;
          } break;
          default:
            std::cerr << "Unhandled generic nickname: "
                      << node.m_genericNickname << std::endl;
        }
      }
      break;
    }
    case kCDXNodeType_Unspecified:
      break;
    case kCDXNodeType_ElementListNickname:
      break;
    case kCDXNodeType_Formula:
      break;
    case kCDXNodeType_AnonymousAlternativeGroup:
      break;
    case kCDXNodeType_NamedAlternativeGroup:
      break;
    case kCDXNodeType_MultiAttachment:
      break;
    case kCDXNodeType_VariableAttachment:
      break;
    case kCDXNodeType_LinkNode:
      break;
    case kCDXNodeType_Monomer:
      break;
  }

  for (auto &child : node.ContainedObjects()) {
    if (child.second->GetTag() == kCDXObj_Text) {
      const std::string &text = ((CDXText *)child.second)->GetText().str();
      if (text.size() > 0 && text[0] == 'R') {
        try {
          if (checkForRGroup)
            rgroup_num = text.size() > 1 ? stoi(text.substr(1)) : 0;
          else
            isotope = text.size() > 1 ? stoi(text.substr(1)) : 0;
        } catch (const std::invalid_argument &e) {
          if (rgroup_num)
            BOOST_LOG(rdWarningLog)
                << "RGroupError: Invalid argument - Cannot convert '" << text
                << "' to an integer." << std::endl;
        } catch (const std::out_of_range &e) {
          if (rgroup_num)
            BOOST_LOG(rdWarningLog)
                << "RGroupError: Out of range - The number '" << text
                << "' is too large or too small." << std::endl;
        }
      }
    }
  }

  StereoGroupType grouptype = StereoGroupType::STEREO_ABSOLUTE;
  switch (node.m_enhancedStereoType) {
    case kCDXEnhancedStereo_Absolute:
      grouptype = StereoGroupType::STEREO_ABSOLUTE;
      break;
    case kCDXEnhancedStereo_And:
      grouptype = StereoGroupType::STEREO_AND;
      break;
    case kCDXEnhancedStereo_Or:
      grouptype = StereoGroupType::STEREO_OR;
      break;
    default:
      break;
  }

  CHECK_INVARIANT(atom_id != -1, "Uninitialized atom id in cdxml.");
  Atom *rd_atom = new Atom(elemno);
  rd_atom->setFormalCharge(charge);
  rd_atom->setNumExplicitHs(num_hydrogens);
  rd_atom->setNoImplicit(explicitHs);

  rd_atom->setIsotope(isotope);
  if (rgroup_num >= 0) {
    rd_atom->setAtomMapNum(rgroup_num);
  }
  set_fuse_label(rd_atom, atommap);
  switch (node.m_hStereo) {
    case kCDXProp_Atom_HDot:  // this atom has an implicit hydrogen with a
                              // wedged bond
      rd_atom->setProp<char>(CDX_IMPLICIT_HYDROGEN_STEREO, 'w');
      break;
    case kCDXProp_Atom_HDash:  // this atom has an implicit hydrogen with a
                               // hashed bond
      rd_atom->setProp<char>(CDX_IMPLICIT_HYDROGEN_STEREO, 'h');
      break;
  }
  
  if (node.m_bondOrdering) {
    // This node may be completely replaced by the fragment
    // i.e. [*:1]C[*:1].C[*:1]C => CCC
    rd_atom->setProp<std::vector<int>>(CDX_BOND_ORDERING, *node.m_bondOrdering);
  }
  if (node.m_geometry == kCDXAtomGeometry_Tetrahedral) {
    // std::cerr << "tetrahedral" << std::endl;
    //  if we have a cip type we can interpret, set it, otherwise don't

    switch (node.m_CIP) {
      case kCDXCIPAtom_R:
      case kCDXCIPAtom_r:
      case kCDXCIPAtom_S:
      case kCDXCIPAtom_s:
        rd_atom->setProp<CDXAtomCIPType>(CDX_CIP, node.m_CIP);
        break;
      default:
        rd_atom->setProp<CDXAtomCIPType>(CDX_CIP, kCDXCIPAtom_Undetermined);
        break;
    }
  }

  std::vector<double> atom_coords;
  if (node.KnownPosition3D()) {
    atom_coords.reserve(3);
    atom_coords.push_back(node.m_3dPosition.x);
    atom_coords.push_back(node.m_3dPosition.y);
    atom_coords.push_back(node.m_3dPosition.z);
  } else {
    atom_coords.reserve(2);
    atom_coords.push_back(node.m_2dPosition.x);
    atom_coords.push_back(node.m_2dPosition.y);
  }
  rd_atom->setProp<std::vector<double>>(CDX_ATOM_POS, atom_coords);
  rd_atom->setProp<unsigned int>(CDX_ATOM_ID, atom_id);

  const bool updateLabels = true;
  const bool takeOwnership = true;
  auto idx = mol.addAtom(rd_atom, updateLabels, takeOwnership);
  if (query_label.size()) {
    if (query_label[0] == 'R') {
      rd_atom = addquery(makeAtomNullQuery(), query_label, mol, idx);
    } else if (query_label == "A") {
      rd_atom = addquery(makeAAtomQuery(), query_label, mol, idx);
    } else if (query_label == "Q") {
      rd_atom = addquery(makeQAtomQuery(), query_label, mol, idx);
    } else if (query_label == "M") {
      rd_atom = addquery(makeMAtomQuery(), query_label, mol, idx);
    } else if (query_label == "MH") {
      rd_atom = addquery(makeMHAtomQuery(), query_label, mol, idx);
    } else if (query_label == "X") {
      rd_atom = addquery(makeXAtomQuery(), query_label, mol, idx);
    } else if (query_label == "ElementList") {
      if (!elementlist.size()) {
        BOOST_LOG(rdWarningLog)
            << "ElementList is empty, ignoring..." << std::endl;
      } else {
        auto *q = new ATOM_OR_QUERY;
        q->setDescription("AtomOr");
        for (auto atNum : elementlist) {
          q->addChild(
              QueryAtom::QUERYATOM_QUERY::CHILD_TYPE(makeAtomNumQuery(atNum)));
        }
        rd_atom = addquery(q, query_label, mol, idx);
        rd_atom->setAtomicNum(elementlist.front());
      }
    } else if (query_label.size()) {
      std::cerr << "Unhandled generic nickname: " << query_label << std::endl;
    } else {
      rd_atom->setProp(common_properties::atomLabel, query_label);
    }
  }

  switch (node.m_radical) {
    case kCDXRadical_None:
      break;
    case kCDXRadical_Singlet:
      rd_atom->setNumRadicalElectrons(2);
      break;
    case kCDXRadical_Doublet: {
      rd_atom->setNumRadicalElectrons(1);
      break;
    }
    case kCDXRadical_Triplet: {
      rd_atom->setNumRadicalElectrons(2);
      break;
    }
  }

  if (node.m_enhancedStereoGroupNum > 0) {
    auto key = std::make_pair(node.m_enhancedStereoGroupNum, grouptype);
    auto &stereo = sgroups[key];
    stereo.sgroup = node.m_enhancedStereoGroupNum;
    stereo.grouptype = grouptype;
    stereo.atoms.push_back(rd_atom);
  }

  pagedata.atomIds[atom_id] =
      rd_atom;  // The mol has ownership so this can't leak
  if (node.m_nodeType == kCDXNodeType_Nickname ||
      node.m_nodeType == kCDXNodeType_Fragment) {
    // This fragment needs to be expanded and joined to the current one
    //  the external_id is the node's atom_id
    for (auto fragment : node.ContainedObjects()) {
      if (fragment.second->GetTag() == kCDXObj_Fragment) {
        if (!parseFragment(mol, (CDXFragment &)(*fragment.second), pagedata,
                           missingFragId, atom_id)) {
          return false;
        }
        mol.setProp<bool>(NEEDS_FUSE, true);
        // might need to reset to OUR frag_id since parse_fragment will
        // set
        //  it to the fragments
        mol.setProp(CDX_FRAG_ID, fragmentId);
      }
    }
  }
  return true;
}
}
}  // namespace RDKit