ArticleThe Journal of organic chemistry2015
Tautomerism of Warfarin: Combined Chemoinformatics, Quantum Chemical, and NMR Investigation.
Article in The Journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Improving drug-induced liver injury prediction using graph neural networks with augmented graph features from molecular optimisation.Journal of cheminformatics · 2025Article
- Reliable gas-phase tautomer equilibria of drug-like molecule scaffolds and the issue of continuum solvation.Journal of computer-aided molecular design · 2022Article
- Assigning confidence to molecular property prediction.Expert opinion on drug discovery · 2021Article
- Pattern-free generation and quantum mechanical scoring of ring-chain tautomers.Journal of computer-aided molecular design · 2021Article
- Antagonists of Vitamin K-Popular Coumarin Drugs and New Synthetic and Natural Coumarin Derivatives.Molecules (Basel, Switzerland) · 2020Review
- Experimental and Chemoinformatics Study of Tautomerism in a Database of Commercially Available Screening Samples.Journal of chemical information and modeling · 2016Article
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Authors and funding
3 authors.
Funding
Abstract
Warfarin, an important anticoagulant drug, can exist in solution in 40 distinct tautomeric forms through both prototropic tautomerism and ring-chain tautomerism. We have investigated all warfarin tautomers with computational and NMR approaches. Relative energies calculated at the B3LYP/6-311G++(d,p) level of theory indicate that the 4-hydroxycoumarin cyclic hemiketal tautomer is the most stable tautomer in aqueous solution, followed by the 4-hydroxycoumarin open-chain tautomer. This is in agreement with our NMR experiments where the spectral assignments indicate that warfarin exists mainly as a mixture of cyclic hemiketal diastereomers, with an open-chain tautomer as a minor component. We present a diagram of the interconversion of warfarin created taking into account the calculated equilibrium constants (pK(T)) for all tautomeric reactions. These findings help with gaining further understanding of proton transfer and ring closure tautomerization processes. We also discuss the results in the context of chemoinformatics rules for handling tautomerism.
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