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PLoS One. 2014 Jul 14;9(7):e102069. doi: 10.1371/journal.pone.0102069. eCollection 2014.

Asymmetric clustering index in a case study of 5-HT1A receptor ligands.

Author information

1
Faculty of Mathematics and Computer Science, Jagiellonian University, Kraków, Poland.
2
Institute of Pharmacology, Polish Academy of Sciences, Kraków, Poland.

Abstract

The automatic clustering of chemical compounds is an important branch of chemoinformatics. In this paper the Asymmetric Clustering Index (Aci) is proposed to assess how well an automatically created partition reflects the reference. The asymmetry allows for a distinction between the fixed reference and the numerically constructed partition. The introduced index is applied to evaluate the quality of hierarchical clustering procedures for 5-HT1A receptor ligands. We find that the most appropriate combination of parameters for the hierarchical clustering of compounds with a determined activity for this biological target is the Klekota Roth fingerprint combined with the complete linkage function and the Buser similarity metric.

PMID:
25019251
PMCID:
PMC4096758
DOI:
10.1371/journal.pone.0102069
[Indexed for MEDLINE]
Free PMC Article

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