text: user15359: How would one parse the SMILES string
   BrC[2]:C[3]:C(:CH:CH:CH:@2):CH:CH:CH:CH:@3
  
  I rely on tools like rdkit and OpenBabel to parse SMILES, but both tools aren't able to parse this string.
  More specifically, this SMILES string comes from the supplementary information of a 2007 paper on solubility prediction. After doing some searching, it seems that this paper was received prior to the 2007 standardization of OpenSMILES (this might be why canonical parsers like rdkit have trouble with it).
  After searching a bit more, I found an older PubChem sketcher that was able to convert the SMILES in question into a more recognizable format
   (BrC1=C(C(=C(C2=C1C(=C(C(=C2[H])[H])[H])[H])[H])[H])[H])
  
  (parsing this was successful via rdkit, see molecule image below) but still need a way to convert similarly-formatted SMILES strings into the OpenSMILES standard/canonical format en mass.
  
  
  user15359: I couldn't find a way to directly convert these SMILES strings to a more canonical format. However, thanks to @Matteo Ferla, I was able to get around the problem entirely by looking up the chemical names  and resolving the canonical SMILES programmatically.
  More specifically, I used the CAS no column given in the supplementary information of the referenced paper to pull the SMILES via Chemical Identifier Resolver. See this answer for an explanation on how to do so.
  EDIT: Some of the CAS nos couldn't be resolved, so I manually converted them using the PubChem sketcher tool mentioned in the question. There are quite a few (~160) of such molecules, so if anyone needs the full parsed dataset but doesn't want to spend the time manually parsing those molecules, let me know.
  
original_text: 15359: <p>How would one parse the SMILES string</p>
  <pre><code> BrC[2]:C[3]:C(:CH:CH:CH:@2):CH:CH:CH:CH:@3
  </code></pre>
  <p>I rely on tools like <code>rdkit</code> and <code>OpenBabel</code> to parse SMILES, but both tools aren't able to parse this string.</p>
  <p>More specifically, this SMILES string comes from the supplementary information of a <a href="https://pubs.acs.org/doi/10.1021/ci700096r" rel="nofollow noreferrer">2007 paper on solubility prediction</a>. After doing some searching, it seems that this paper was received prior to the 2007 standardization of OpenSMILES (this might be why canonical parsers like <code>rdkit</code> have trouble with it).</p>
  <p>After searching a bit more, I found an <a href="https://pubchem.ncbi.nlm.nih.gov//edit3/index.html" rel="nofollow noreferrer">older PubChem sketcher</a> that was able to convert the SMILES in question into a more recognizable format</p>
  <pre><code> (BrC1=C(C(=C(C2=C1C(=C(C(=C2[H])[H])[H])[H])[H])[H])[H])
  </code></pre>
  <p>(parsing this was successful via <code>rdkit</code>, see molecule image below) but still need a way to convert similarly-formatted SMILES strings into the OpenSMILES standard/canonical format en mass.</p>
  <p><a href="https://i.stack.imgur.com/j4TC9.png" rel="nofollow noreferrer"><img src="https://i.stack.imgur.com/j4TC9.png" alt="image for BrC1=C(C(=C(C2=C1C(=C(C(=C2[H])[H])[H])[H])[H])[H])[H]" /></a></p>
   15359: <p>I couldn't find a way to directly convert these SMILES strings to a more canonical format. However, thanks to <a href="https://bioinformatics.stackexchange.com/users/6322/matteo-ferla">@Matteo Ferla</a>, I was able to get around the problem entirely by looking up the chemical names  and resolving the canonical SMILES programmatically.</p>
  <p>More specifically, I used the CAS no column given in the supplementary information of the referenced paper to pull the SMILES via <a href="https://cactus.nci.nih.gov/chemical/structure" rel="nofollow noreferrer">Chemical Identifier Resolver</a>. See <a href="https://stackoverflow.com/a/54932071/12215814">this answer</a> for an explanation on how to do so.</p>
  <p><strong>EDIT</strong>: Some of the CAS nos couldn't be resolved, so I manually converted them using the PubChem sketcher tool mentioned in the question. There are quite a few (~160) of such molecules, so if anyone needs the full parsed dataset but doesn't want to spend the time manually parsing those molecules, let me know.</p>
  