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Quest for the rings. In silico exploration of ring universe to identify novel bioactive heteroaromatic scaffolds.

Ertl, Peter and Jelfs, Stephen and Mühlbacher, Jörg and Schuffenhauer, Ansgar and Selzer, Paul (2006) Quest for the rings. In silico exploration of ring universe to identify novel bioactive heteroaromatic scaffolds. Journal of Medicinal Chemistry, 49 (15). pp. 4568-4573. ISSN 0022-2623

Abstract

Bioactive molecules only contain a relatively limited number of unique ring types. To identify those ring properties and structural characteristics that are necessary for biological activity, a large virtual library of nearly 600 000 heteroaromatic scaffolds was created and characterized by calculated properties, including structural features, bioavailability descriptors, and quantum chemical parameters. A self-organizing neural network was used to cluster these scaffolds and to identify properties that best characterize bioactive ring systems. The analysis shows that bioactivity is very sparsely distributed within the scaffold property and structural space, forming only several relatively small, well-defined "bioactivity islands". Various possible applications of a large database of rings with calculated properties and bioactivity scores in the drug design and discovery process are discussed, including virtual screening, support for the design of combinatorial libraries, bioisosteric design, and scaffold hopping.

Item Type: Article
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Date Deposited: 14 Dec 2009 14:00
Last Modified: 31 Jan 2013 01:18
URI: https://oak.novartis.com/id/eprint/389

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