fixes #7295 (#7303)

rdkit · Mar 28, 2024 · 0a0b158 · 0a0b158
1 parent eebad84
commit 0a0b158
Show file tree

Hide file tree

Showing 2 changed files with 17 additions and 3 deletions.
diff --git a/Code/GraphMol/SmilesParse/SmilesWrite.cpp b/Code/GraphMol/SmilesParse/SmilesWrite.cpp
@@ -371,7 +371,6 @@ std::string FragmentSmilesConstruct(
   if (params.canonical && params.doIsomericSmiles) {
     Canon::canonicalizeEnhancedStereo(mol, &ranks);
   }
-
   Canon::canonicalizeFragment(mol, atomIdx, colors, ranks, molStack,
                               bondsInPlay, bondSymbols, params.doIsomericSmiles,
                               params.doRandom);
@@ -521,11 +520,10 @@ std::string MolToSmiles(const ROMol &mol, const SmilesWriteParams &params,
     // but that should not be:
     if (params.doIsomericSmiles) {
       tmol->setProp(common_properties::_doIsoSmiles, 1);
-      if (!mol.hasProp(common_properties::_StereochemDone)) {
+      if (!tmol->hasProp(common_properties::_StereochemDone)) {
         MolOps::assignStereochemistry(*tmol, true);
       }
     }
-
     if (!doingCXSmiles) {
       // remove any stereo groups that may be present. Otherwise they will be
       // used in the canonicalization

diff --git a/Code/GraphMol/SmilesParse/catch_tests.cpp b/Code/GraphMol/SmilesParse/catch_tests.cpp
@@ -2790,4 +2790,20 @@ TEST_CASE("leaks on unclosed rings") {
     auto m = "C1C)foo"_smiles;
     REQUIRE(!m);
   }
+}
+
+TEST_CASE("Github #7295") {
+  SECTION("basics") {
+    auto m = "C[C@@H]1CC[C@@H](C(=O)O)CC1.Cl"_smiles;
+    REQUIRE(m);
+    auto smi1 = MolToSmiles(*m);
+    m->clearComputedProps();
+    auto smi2 = MolToSmiles(*m);
+    CHECK(smi1 == smi2);
+    auto m2(*m);
+    bool cleanIt=true;
+    MolOps::assignStereochemistry(m2, cleanIt);
+    auto smi3 = MolToSmiles(m2);
+    CHECK(smi1 == smi3);
+  }
 }