Only in Experiment 3 were all the generated IUPAC names retranslated back into SMILES using OPSIN. OPSIN was chosen because it systematically parses IUPAC names with a defined set of rules. The retranslated SMILES strings were compared with the original SMILES strings to determine the similarity between the original and predicted structures. Identical structures and the Tanimoto similarity indices (using PubChem fingerprints) were evaluated.