ArticleJournal of chemical information and modeling2020
Toward a Comprehensive Treatment of Tautomerism in Chemoinformatics Including in InChI V2.
Article in Journal of chemical information and modeling, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Deep learning of tautomer stability from crystallographic proton positions.Chemical science · 2026Article
- pKa prediction for small molecules: an overview of experimental, quantum, and machine learning-based approaches.Journal of computer-aided molecular design · 2025Review
- Machine Learning for Toxicity Prediction Using Chemical Structures: Pillars for Success in the Real World.Chemical research in toxicology · 2025Review
- Fast and Accurate Prediction of Tautomer Ratios in Aqueous Solution via a Siamese Neural Network.Journal of chemical theory and computation · 2025Article
- What impact does tautomerism have on drug discovery and development?Expert opinion on drug discovery · 2024Article
- QupKake: Integrating Machine Learning and Quantum Chemistry for Micro-pJournal of chemical theory and computation · 2024Article
- IUPAC International Chemical Identifier (InChI)-related education and training materials through InChI Open Education Resource (OER).Chemistry Teacher International : best practices in chemistry education · 2024Article
- Free and open-source QSAR-ready workflow for automated standardization of chemical structures in support of QSAR modeling.Journal of cheminformatics · 2024Article
- Challenges and perspectives for naming lipids in the context of lipidomics.Metabolomics : Official journal of the Metabolomic Society · 2024Review
- The in-silico evaluation of important GLUT9 residue for uric acid transport based on renal hypouricemia type 2.Chemico-biological interactions · 2023Article
- Guided discovery of chemical reaction pathways with imposed activation.Chemical science · 2022Article
- canSAR chemistry registration and standardization pipeline.Journal of cheminformatics · 2022Article
- Atomistic mechanisms of the tautomerization of the G·C base pairs through the proton transfer: quantum-chemical survey.Journal of molecular modeling · 2021Article
- Automated Exploration of Prebiotic Chemical Reaction Space: Progress and Perspectives.Life (Basel, Switzerland) · 2021Review
- Novel mechanisms of the conformational transformations of the biologically important G·C nucleobase pairs in Watson-Crick, Hoogsteen and wobble configurationsRSC advances · 2021Article
- Exploring the octanol-water partition coefficient dataset using deep learning techniques and data augmentation.Communications chemistry · 2021Article
- InChI version 1.06: now more than 99.99% reliable.Journal of cheminformatics · 2021Article
- Pattern-free generation and quantum mechanical scoring of ring-chain tautomers.Journal of computer-aided molecular design · 2021Article
- Tautomer Database: A Comprehensive Resource for Tautomerism Analyses.Journal of chemical information and modeling · 2020Article
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5 authors.
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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.
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