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Use of reduced graphs to encode bioisosterism for similarity-based virtual screening

Birchall, K., Gillet, V.J., Willett, P., Ducrot, P. and Luttman, C. (2009) Use of reduced graphs to encode bioisosterism for similarity-based virtual screening. Journal of Chemical Information and Modeling, 49 (6). pp. 1330-1346. ISSN 1549-9596

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Abstract

This paper describes a project to include explicit information about bioisosteric equivalences between pairs of fragment substructures in a system for similarity-based virtual screening. Data from the BIOSTER database show that reduced graphs provide a simple way of encoding known bioisosteric equivalences in a manner that can be used during similarity searching. Scaffold-hopping experiments with the WOMBAT database show that including such information enables similarities to be identified between the reference structures and active structures from the database that contain different, but equivalent, fragment substructures. However, such equivalences also contribute to the similarities between the reference structures and inactives, and the latter equivalences can swamp those involving the actives. This presents serious problems for the routine use of information about bioisosteric fragments in similarity-based virtual screening.

Item Type: Article
Academic Units: The University of Sheffield > Faculty of Social Sciences (Sheffield) > Information School (Sheffield)
Depositing User: Miss Anthea Tucker
Date Deposited: 28 Sep 2009 12:23
Last Modified: 28 Sep 2009 12:23
Published Version: http://dx.doi.org/10.1021/ci900078h
Status: Published
Publisher: American Chemical Society
Identification Number: 10.1021/ci900078h
URI: http://eprints.whiterose.ac.uk/id/eprint/9786

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