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Gardiner, E.J., Holliday, J.D., O'Dowd, C. et al. (1 more author) (2011) Effectiveness of 2D fingerprints for scaffold hopping. Future Medicinal Chemistry, 3 (4). 405 - 414. ISSN 1756-8919
Abstract
Background: It has been suggested that similarity searching using 2D fingerprints may not be suitable for scaffold hopping. Methods: This article reports a detailed evaluation of the effectiveness of six common types of 2D fingerprints when they are used for scaffold-hopping similarity searches of the Molecular Design Limited Drug Data Report database, World of Molecular Bioactivity database and Maximum Unbiased Validation database. Results: The results demonstrate that 2D fingerprints can be used for scaffold hopping, with novel scaffolds being identified in nearly every search that was carried out. The degree of enrichment depends on the structural diversity of the actives that are being sought, with the greatest enrichments often being obtained using the extended connectivity fingerprint encoding a circular substructure of diameter four bonds (ECFP4) fingerprint. Conclusion: 2D fingerprints provide a simple and computationally efficient way of identifying novel chemotypes in lead-discovery programs.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2011 Future Science. This is an author produced version of a paper subsequently published in Future Medicinal Chemistry. Uploaded in accordance with the publisher's self-archiving policy. |
Keywords: | Data fusion; Similarity |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Social Sciences (Sheffield) > Information School (Sheffield) |
Depositing User: | Miss Anthea Tucker |
Date Deposited: | 20 Nov 2013 15:32 |
Last Modified: | 23 Jun 2023 21:34 |
Published Version: | http://dx.doi.org/10.4155/FMC.11.4 |
Status: | Published |
Publisher: | Future Science |
Identification Number: | 10.4155/FMC.11.4 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:76255 |
Available Versions of this Item
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Effectiveness of 2D fingerprints for scaffold hopping. (deposited 01 Jun 2011 09:31)
- Effectiveness of 2D fingerprints for scaffold hopping. (deposited 20 Nov 2013 15:32) [Currently Displayed]