Tags

Type your tag names separated by a space and hit enter

Toward a Comprehensive Treatment of Tautomerism in Chemoinformatics Including in InChI V2.
J Chem Inf Model. 2020 Mar 23; 60(3):1253-1275.JC

Abstract

We have collected 86 different transforms of tautomeric interconversions. Out of those, 54 are for prototropic (non-ring-chain) tautomerism, 21 for ring-chain tautomerism, and 11 for valence tautomerism. The majority of these rules have been extracted from experimental literature. Twenty rules, covering the most well-known types of tautomerism such as keto-enol tautomerism, were taken from the default handling of tautomerism by the chemoinformatics toolkit CACTVS. The rules were analyzed against nine differerent databases totaling over 400 million (non-unique) structures as to their occurrence rates, mutual overlap in coverage, and recapitulation of the rules' enumerated tautomer sets by InChI V.1.05, both in InChI's Standard and a Nonstandard version with the increased tautomer-handling options 15T and KET turned on. These results and the background of this study are discussed in the context of the IUPAC InChI Project tasked with the redesign of handling of tautomerism for an InChI version 2. Applying the rules presented in this paper would approximately triple the number of compounds in typical small-molecule databases that would be affected by tautomeric interconversion by InChI V2. A web tool has been created to test these rules at https://cactus.nci.nih.gov/tautomerizer.

Authors+Show Affiliations

Computer-Aided Drug Design Group, Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, NIH, Frederick, Maryland 21702, United States.Xemistry GmbH, Hainholzweg 11, D-61479 Glashütten, Germany.Computer-Aided Drug Design Group, Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, NIH, Frederick, Maryland 21702, United States.Computer-Aided Drug Design Group, Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, NIH, Frederick, Maryland 21702, United States.Computer-Aided Drug Design Group, Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, NIH, Frederick, Maryland 21702, United States.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32043883

Citation

Dhaked, Devendra K., et al. "Toward a Comprehensive Treatment of Tautomerism in Chemoinformatics Including in InChI V2." Journal of Chemical Information and Modeling, vol. 60, no. 3, 2020, pp. 1253-1275.
Dhaked DK, Ihlenfeldt WD, Patel H, et al. Toward a Comprehensive Treatment of Tautomerism in Chemoinformatics Including in InChI V2. J Chem Inf Model. 2020;60(3):1253-1275.
Dhaked, D. K., Ihlenfeldt, W. D., Patel, H., Delannée, V., & Nicklaus, M. C. (2020). Toward a Comprehensive Treatment of Tautomerism in Chemoinformatics Including in InChI V2. Journal of Chemical Information and Modeling, 60(3), 1253-1275. https://doi.org/10.1021/acs.jcim.9b01080
Dhaked DK, et al. Toward a Comprehensive Treatment of Tautomerism in Chemoinformatics Including in InChI V2. J Chem Inf Model. 2020 Mar 23;60(3):1253-1275. PubMed PMID: 32043883.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Toward a Comprehensive Treatment of Tautomerism in Chemoinformatics Including in InChI V2. AU - Dhaked,Devendra K, AU - Ihlenfeldt,Wolf-Dietrich, AU - Patel,Hitesh, AU - Delannée,Victorien, AU - Nicklaus,Marc C, Y1 - 2020/03/10/ PY - 2020/2/12/pubmed PY - 2020/2/12/medline PY - 2020/2/12/entrez SP - 1253 EP - 1275 JF - Journal of chemical information and modeling JO - J Chem Inf Model VL - 60 IS - 3 N2 - We have collected 86 different transforms of tautomeric interconversions. Out of those, 54 are for prototropic (non-ring-chain) tautomerism, 21 for ring-chain tautomerism, and 11 for valence tautomerism. The majority of these rules have been extracted from experimental literature. Twenty rules, covering the most well-known types of tautomerism such as keto-enol tautomerism, were taken from the default handling of tautomerism by the chemoinformatics toolkit CACTVS. The rules were analyzed against nine differerent databases totaling over 400 million (non-unique) structures as to their occurrence rates, mutual overlap in coverage, and recapitulation of the rules' enumerated tautomer sets by InChI V.1.05, both in InChI's Standard and a Nonstandard version with the increased tautomer-handling options 15T and KET turned on. These results and the background of this study are discussed in the context of the IUPAC InChI Project tasked with the redesign of handling of tautomerism for an InChI version 2. Applying the rules presented in this paper would approximately triple the number of compounds in typical small-molecule databases that would be affected by tautomeric interconversion by InChI V2. A web tool has been created to test these rules at https://cactus.nci.nih.gov/tautomerizer. SN - 1549-960X UR - https://www.unboundmedicine.com/medline/citation/32043883/Toward_a_Comprehensive_Treatment_of_Tautomerism_in_Chemoinformatics_Including_in_InChI_V2 L2 - https://doi.org/10.1021/acs.jcim.9b01080 DB - PRIME DP - Unbound Medicine ER -
Try the Free App:
Prime PubMed app for iOS iPhone iPad
Prime PubMed app for Android
Prime PubMed is provided
free to individuals by:
Unbound Medicine.