Enhancing the Effectiveness of Fingerprint-Based Virtual Screening: Use of Turbo Similarity Searching and of Fragment Frequencies of Occurrence

  • Shereena M. Arif
  • Jérôme Hert
  • John D. Holliday
  • Nurul Malim
  • Peter Willett
Part of the Lecture Notes in Computer Science book series (LNCS, volume 5780)

Abstract

Binary fingerprints encoding the presence of 2D fragment substructures in molecules are extensively used for similarity-based virtual screening in the agrochemical and pharmaceutical industries. This paper describes two techniques for enhancing the effectiveness of screening: the use of a second-level search based on the nearest neighbours of the initial reference structure; and the use of weighted fingerprints encoding the frequency of occurrence, rather than just the mere presence, of substructures. Experiments using several databases for which both structural and bioactivity data are available demonstrate the effectiveness of these two approaches.

Keywords

Chemoinformatics Fingerprint Fragment substructure Similarity measure Similarity searching Turbo similarity searching Virtual screening Weighting scheme 

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Copyright information

© Springer-Verlag Berlin Heidelberg 2009

Authors and Affiliations

  • Shereena M. Arif
    • 1
  • Jérôme Hert
    • 1
  • John D. Holliday
    • 1
  • Nurul Malim
    • 1
  • Peter Willett
    • 1
  1. 1.Krebs Institute for Biomolecular Research and Department of Information StudiesUniversity of SheffieldSheffieldUnited Kingdom

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