title: Comparison of chemical clustering methods using graph- and fingerprint-based similarity measures.
abstract: This paper compares several published methods for clustering chemical structures, using both graph- and fingerprint-based similarity measures. The clusterings from each method were compared to determine the degree of cluster overlap. Each method was also evaluated on how well it grouped structures into clusters possessing a non-trivial substructural commonality. The methods which employ adjustable parameters were tested to determine the stability of each parameter for datasets of varying size and composition. Our experiments suggest that both graph- and fingerprint-based similarity measures can be used effectively for generating chemical clusterings; it is also suggested that the CAST and Yin-Chen methods, suggested recently for the clustering of gene expression patterns, may also prove effective for the clustering of 2D chemical structures.
authors.affiliation: Pfizer Global Research and Development, Ann Arbor Laboratories, 2800 Plymouth Road, Ann Arbor, MI 48105, USA. john.raymond@pfizer.com
authors.forename: John W
authors.initials: JW
authors.lastname: Raymond
authors.forename: C John
authors.initials: CJ
authors.lastname: Blankley
authors.forename: Peter
authors.initials: P
authors.lastname: Willett
mesh_terms: D000465:Algorithms; D016000:Cluster Analysis; D015394:Molecular Structure; D012984:Software