Tautomerism in Computer‐Aided Drug Design
- 1 January 2003
- journal article
- review article
- Published by Taylor & Francis in Journal of Receptors and Signal Transduction
- Vol. 23 (4) , 361-371
- https://doi.org/10.1081/rrs-120026975
Abstract
Tautomers are often disregarded in computer‐aided molecular modeling applications. Little is known about the different tautomeric states of a molecule and they are rarely registered in chemical databases. Tautomeric forms of a molecule differ in shape, functional groups, surface, and hydrogen‐bonding pattern. Calculation of physical–chemical properties and molecular descriptors differ from one tautomeric state to the other as it is demonstrated with an example of the log P calculation, similarity index, and the complementarity pattern to the targeted protein. Considering tautomery in ligand–protein interactions therefore has a significant impact on the prediction of the ligand binding using various docking techniques. This article points on hitherto unaddressed issue of tautomerism in computer‐aided drug design.Keywords
This publication has 27 references indexed in Scilit:
- Advanced Exact Structure Searching in Large Databases of Chemical CompoundsJournal of Chemical Information and Computer Sciences, 2003
- Chemical database techniques in drug discoveryNature Reviews Drug Discovery, 2002
- Virtual screening and fast automated docking methodsDrug Discovery Today, 2002
- Prediction of Physicochemical PropertiesPublished by Wiley ,2000
- Understanding Receptor‐Ligand Interactions as a Prerequisite for—Virtual ScreeningPublished by Wiley ,2000
- Chemical Similarity SearchingJournal of Chemical Information and Computer Sciences, 1998
- On the Properties of Bit String-Based Measures of Chemical SimilarityJournal of Chemical Information and Computer Sciences, 1998
- Intramolecular Interactions Encoded in Lipophilicity: Their Nature and SignificancePublished by Wiley ,1996
- A new model for the agonistic binding site on the histamine H2-receptor: The catalytic triad in serine proteases as a model for the binding site ofJournal of Molecular Graphics, 1994
- The Chemical Abstracts Service Chemical Registry System. VII. Tautomerism and Alternating BondsJournal of Chemical Information and Computer Sciences, 1980