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Properties of Known Drugs. 2. Side Chains
Abstract
We continue our study of the common features present in drug molecules by looking in detail at drug side chains. Using shape description methods, we divide a database of commercially available drugs into a list of common drug side chains. On the basis of the atom pair shape descriptor (taking into account atom type, hybridization, and bond order), there are 1,246 different side chains among the 5,090 compounds analyzed. The average number of side chains per molecule is 4, and the average number of heavy atoms per side chain is 2. If we ignore the carbonyl side chain, then there are approximately 15,000 occurrences of side chains. Of these 15,000 approximately 11,000 are from the "top 20" group of side chains. This suggests that the diversity that side chains provide to drug molecules is quite low. We discuss ways that this work could be used to provide guidance for molecular design efforts.
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Cites
Can We Learn To Distinguish between “Drug-like” and “Nondrug-like” Molecules?
Ajay, Walters, W. P., & Murcko, M. A. (1998) · Journal of Medicinal Chemistry · doi:10.1021/jm970666c · Cited by 484
Self-citation
Cited by
Simple Selection Criteria for Drug-like Chemical Matter
Muegge, I., Heald, S. L., & Brittelli, D. (2001) · Journal of Medicinal Chemistry · doi:10.1021/jm015507e · Cited by 1,315
Reymond, J.-L. (2015) · Accounts of Chemical Research · doi:10.1021/ar500432k · Cited by 720
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
Fragment Informatics and Computational Fragment‐Based Drug Design: An Overview and Update
Sheng, C., & Zhang, W. (2013) · Medicinal Research Reviews · doi:10.1002/med.21255 · Cited by 80
Metadata
- Authors
- Bemis, G. W., & Murcko, M. A.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-12-01
- Volume
- 42
- Issue
- 25
- Pages
- 5095-5099
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2003932717
- Cited by
- 271
- References
- 1
- FWCI
- 14.76
- Type
- journal article
- Language
- en
- Open access
- closed
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