The DOI matches its Crossref record; 4 of the 4 references it cites were found in a registry or an index.
Molecular Similarity in Medicinal Chemistry: Miniperspective
Abstract
Similarity is a subjective and multifaceted concept, regardless of whether compounds or any other objects are considered. Despite its intrinsically subjective nature, attempts to quantify the similarity of compounds have a long history in chemical informatics and drug discovery. Many computational methods employ similarity measures to identify new compounds for pharmaceutical research. However, chemoinformaticians and medicinal chemists typically perceive similarity in different ways. Similarity methods and numerical readouts of similarity calculations are probably among the most misunderstood computational approaches in medicinal chemistry. Herein, we evaluate different similarity concepts, highlight key aspects of molecular similarity analysis, and address some potential misunderstandings. In addition, a number of practical aspects concerning similarity calculations are discussed.
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Cites
ChEMBL: a large-scale bioactivity database for drug discovery
Gaulton, A., Bellis, L. J., Bento, A. P., Chambers, J., Davies, M., Hersey, A., Light, Y., McGlinchey, S., Michalovich, D., Al-Lazikani, B., et al. (2012) · Nucleic Acids Research · doi:10.1093/nar/gkr777 · Cited by 4,382
Similarity-based virtual screening using 2D fingerprints
Willett, P. (2006) · Drug Discovery Today · doi:10.1016/j.drudis.2006.10.005 · Cited by 849
Do Structurally Similar Molecules Have Similar Biological Activity?
Martin, Y. C., Kofron, J. L., & Traphagen, L. M. (2002) · Journal of Medicinal Chemistry · doi:10.1021/jm020155c · Cited by 806
On Outliers and Activity CliffsWhy QSAR Often Disappoints
Maggiora, G. M. (2006) · Journal of Chemical Information and Modeling · doi:10.1021/ci060117s · Cited by 728
Self-citation
Cited by
QSAR Modeling: Where have you been? Where are you going to?
Cherkasov, A., Muratov, E. N., Fourches, D., Varnek, A., Baskin, I. I., Cronin, M., Dearden, J., Gramatica, P., Martin, Y. C., Todeschini, R., et al. (2014) · Journal of Medicinal Chemistry · doi:10.1021/jm4004285 · Cited by 2,164
Muratov, E. N., Bajorath, J., Sheridan, R. P., Tetko, I. V., Filimonov, D., Poroikov, V., Oprea, T. I., Baskin, I. I., Varnek, A., Roitberg, A., et al. (2020) · Chemical Society Reviews · doi:10.1039/d0cs00098a · Cited by 913
Self-citationRecent Advances in Scaffold Hopping: Miniperspective
Hu, Y., Stumpfe, D., & Bajorath, J. (2017) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.6b01437 · Cited by 361
Self-citationIsayev, O., Fourches, D., Muratov, E. N., Oses, C., Rasch, K., Tropsha, A., & Curtarolo, S. (2015) · Chemistry of Materials · doi:10.1021/cm503507h · Cited by 300
What Is High-Throughput Virtual Screening? A Perspective from Organic Materials Discovery
Pyzer-Knapp, E. O., Suh, C., Gómez-Bombarelli, R., Aguilera-Iparraguirre, J., & Aspuru-Guzik, A. (2015) · Annual Review of Materials Research · doi:10.1146/annurev-matsci-070214-020823 · Cited by 299
Metadata
- Authors
- Maggiora, G., Vogt, M., Stumpfe, D., & Bajorath, J.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-11-11
- Volume
- 57
- Issue
- 8
- Pages
- 3186-3204
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2412446857
- Cited by
- 666
- References
- 4
- FWCI
- 37.18
- Type
- journal article
- Language
- en
- Open access
- closed
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