We have conducted a tautomerism analysis in a large database of commercially available compounds. The goal of this analysis is two-fold: to investigate how many cases of the same chemical being sold as different products (at possibly different prices) may occur in aggregated screening sample databases; and to test the tautomerism definition of the widely used chemoinformatics toolkit CACTVS. We applied the default CACTVS transforms to the publicly accessible Aldrich Market Select (AMS) database from ChemNavigator/Sigma-Aldrich, which currently comprises over 8 million unique chemicals available from hundreds of suppliers worldwide. We found thousands of cases where at least two products listed as different compounds in the AMS were declared as tautomeric forms of the same compound by CACTVS. We report on our efforts to address the question of the true tautomeric overlap by selecting a number of tautomer pairs (or larger tuples) from the AMS, and analyzing their structural identity or difference by, e.g., NMR.

Analysis of tautomerism in databases of commercially available compounds

245th National Meeting (2013)

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