The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.
Matched Molecular Pairs as a Guide in the Optimization of Pharmaceutical Properties; a Study of Aqueous Solubility, Plasma Protein Binding and Oral Exposure
Abstract
By identifying every pair of molecules that differ only by a particular, well-defined, structural transformation in a database of measured properties and computing the corresponding change in property, we obtain an overview of the effect that structural change has upon the property and set an expectation for what will happen when that transformation is applied elsewhere. The mean change indicates the expected magnitude of the change in the property and the number of cases in which the property increases give the probability that the structural transformation will cause the property to increase. Outliers indicate potential ways of avoiding the general trend. Comparing to changes in lipophilicity highlights structural transformations that have unusual effects, some of which can be explained by conformational changes. In this paper, we focus upon the effects on aqueous solubility, plasma protein binding and oral exposure of adding substituents to aromatic rings and methylating heteroatoms.
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Cites
The Prediction of Human Pharmacokinetic Parameters from Preclinical and in Vitro Metabolism Data
Obach, R. S., Baxter, J. G., Liston, T. E., Silber, B. M., Jones, B. C., Macintyre, F., Rance, D. J., & Wastall, P. (1997) · The Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(24)36999-x · Cited by 987
Discovery of a potent and selective inhibitor of cyclin-dependent kinase 4/6
Toogood, P. L., Harvey, P. J., Repine, J. T., Sheehan, D. J., VanderWel, S. N., Zhou, H., Keller, P. R., McNamara, D. J., Sherry, D., Zhu, T., et al. (2005) · Journal of Medicinal Chemistry · doi:10.1021/jm049354h · Cited by 513
Cited by
Advancing drug discovery via artificial intelligence
Chan, H. C. S., Shan, H., Dahoun, T., Vogel, H., & Yuan, S. (2019) · Trends in Pharmacological Sciences · doi:10.1016/j.tips.2019.06.004 · Cited by 654
Computationally Efficient Algorithm to Identify Matched Molecular Pairs (MMPs) in Large Data Sets
Hussain, J., & Rea, C. (2010) · Journal of Chemical Information and Modeling · doi:10.1021/ci900450m · Cited by 420
Matched Molecular Pairs as a Medicinal Chemistry Tool: Miniperspective
Griffen, E., Leach, A. G., Robb, G. R., & Warner, D. J. (2011) · Journal of Medicinal Chemistry · doi:10.1021/jm200452d · Cited by 282
Self-citationWard, R. A., Anderton, M. J., Ashton, S., Bethel, P. A., Box, M., Butterworth, S., Colclough, N., Chorley, C. G., Chuaqui, C., Cross, D. A. E., et al. (2013) · Journal of Medicinal Chemistry · doi:10.1021/jm400822z · Cited by 279
Self-citationInterpretation of Quantitative Structure-Activity Relationship Models: Past, Present, and Future
Polishchuk, P. (2017) · Journal of Chemical Information and Modeling · doi:10.1021/acs.jcim.7b00274 · Cited by 236
Metadata
- Authors
- Leach, A. G., Jones, H. D., Cosgrove, D. A., Kenny, P. W., Ruston, L., MacFaul, P., Wood, J. M., Colclough, N., & Law, B.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-10-20
- Volume
- 49
- Issue
- 23
- Pages
- 6672-6682
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2087952495
- Cited by
- 277
- References
- 2
- FWCI
- 8.88
- Type
- journal article
- Language
- en
- Open access
- closed
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- Leach, A. G., Jones, H. D., Cosgrove, D. A., Kenny, P. W., Ruston, L., MacFaul, P., Wood, J. M., Colclough, N., & Law, B. (2006). Matched Molecular Pairs as a Guide in the Optimization of Pharmaceutical Properties; a Study of Aqueous Solubility, Plasma Protein Binding and Oral Exposure. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm0605233
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