Extended-connectivity fingerprints

J Chem Inf Model. 2010 May 24;50(5):742-54. doi: 10.1021/ci100050t.


Extended-connectivity fingerprints (ECFPs) are a novel class of topological fingerprints for molecular characterization. Historically, topological fingerprints were developed for substructure and similarity searching. ECFPs were developed specifically for structure-activity modeling. ECFPs are circular fingerprints with a number of useful qualities: they can be very rapidly calculated; they are not predefined and can represent an essentially infinite number of different molecular features (including stereochemical information); their features represent the presence of particular substructures, allowing easier interpretation of analysis results; and the ECFP algorithm can be tailored to generate different types of circular fingerprints, optimized for different uses. While the use of ECFPs has been widely adopted and validated, a description of their implementation has not previously been presented in the literature.

MeSH terms

  • Algorithms*
  • Databases, Factual*
  • Drug Design*
  • Molecular Structure
  • Structure-Activity Relationship