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Research Article

The Most Common Chemical Replacements in Drug-Like Compounds

Robert P. Sheridan^†

Department of Molecular Systems, RY50SW-100 Merck Research Laboratories, Rahway, New Jersey 07065

J. Chem. Inf. Comput. Sci., 2002, 42 (1), pp 103–108

DOI: 10.1021/ci0100806

Publication Date (Web): January 3, 2002

†

Corresponding author phone: (732)594-3859; fax: (732)594-4224; e-mail: sheridan@merck.com.

Abstract

We have written a method that extracts one-to-one replacements of chemical groups in pairs of drug-like molecules with the same biological activity and counts the frequency of the replacements in a large collection of such molecules. There are two variations on the method that differ in their treatment of replacements in rings. This method is one possible approach to systematically identify candidate bioisosteres. Here we look at the MDDR database because it has a large diversity of drug-like compounds in a large number of therapeutic areas. The most frequent replacements in MDDR seem generally consistent with medicinal chemistry intuition about what chemical groups are equivalent or with groups that are easily converted by synthetic or metabolic pathways. This method can be applied to any set of molecules wherein the molecules can be paired by similar biological activity.

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Published In Issue January 28, 2002
Received August 10, 2001

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Research Article

The Most Common Chemical Replacements in Drug-Like Compounds

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Bioisosterism: A Rational Approach in Drug Design

Cheminformatics Analysis of Organic Substituents: Identification of the Most Common Substituents, Calculation of Substituent Properties, and Automatic Identification of Drug-like Bioisosteric Groups

The Quest for Bioisosteric Replacements

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