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On the hydrophobicity of peptides: comparing empirical predictions of peptide log P values

Thompson, S.J., Hattotuwagama, C.K., Holliday, J.D. and Flower, D. (2006) On the hydrophobicity of peptides: comparing empirical predictions of peptide log P values. Bioinformation, 1 (7). pp. 237-241. ISSN 0973-2063

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Peptides are of great therapeutic potential as vaccines and drugs. Knowledge of physicochemical descriptors, including the partition coefficient logP, is useful for the development of predictive Quantitative Structure-Activity Relationships (QSARs). We have investigated the accuracy of available programs for the prediction of logP values for peptides with known experimental values obtained from the literature. Eight prediction programs were tested, of which seven programs were fragment-based methods: XLogP, LogKow, PLogP, ACDLogP, AlogP, Interactive Analysis’s LogP and MlogP; and one program used a whole molecule approach: QikProp. The predictive accuracy of the programs was assessed using r2 values, with ALogP being the most effective (r2 = 0.822) and MLogP the least (r2 = 0.090). We also examined three distinct types of peptide structure: blocked, unblocked, and cyclic. For each study (all peptides, blocked, unblocked and cyclic peptides) the performance of programs rated from best to worse is as follows: all peptides – ALogP, QikProp, PLogP, XLogP, IALogP, LogKow, ACDLogP, and MlogP; blocked peptides – PLogP, XLogP, ACDLogP, IALogP, LogKow, QikProp, ALogP, and MLogP; unblocked peptides – QikProp, IALogP, ALogP, ACDLogP, MLogP, XLogP, LogKow and PLogP; cyclic peptides – LogKow, ALogP, XLogP, MLogP, QikProp, ACDLogP, IALogP. In summary, all programs gave better predictions for blocked peptides, while, in general, logP values for cyclic peptides were under-predicted and those of unblocked peptides were over-predicted.

Item Type: Article
Keywords: partition coefficient; logP; peptides; octanol; biphasic system; QSAR
Institution: The University of Sheffield
Academic Units: The University of Sheffield > Faculty of Social Sciences (Sheffield) > Information School (Sheffield)
Depositing User: Information Studies
Date Deposited: 26 Aug 2009 09:34
Last Modified: 26 Aug 2009 09:34
Published Version: http://www.bioinformation.net/001/006100012006.htm
Status: Published
Publisher: Biomedical Informatics Publishing Group
URI: http://eprints.whiterose.ac.uk/id/eprint/9227

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