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Torsion Library Reloaded: A New Version of Expert-Derived SMARTS Rules for Assessing Conformations of Small Molecules
- Source :
- Journal of Chemical Information and Modeling. 56:1-5
- Publication Year :
- 2015
- Publisher :
- American Chemical Society (ACS), 2015.
-
Abstract
- The Torsion Library contains hundreds of rules for small molecule conformations which have been derived from the Cambridge Structural Database (CSD) and are curated by molecular design experts. The torsion rules are encoded as SMARTS patterns and categorize rotatable bonds via a traffic light coloring scheme. We have systematically revised all torsion rules to better identify highly strained conformations and minimize the number of false alerts for CSD small molecule X-ray structures. For this new release, we added or substantially modified 78 torsion patterns and reviewed all angles and tolerance intervals. The overall number of red alerts for a filtered CSD data set with 130 000 structures was reduced by a factor of 4 compared to the predecessor. This is of clear advantage in 3D virtual screening where hits should only be removed by a conformational filter if they are in energetically inaccessible conformations.
- Subjects :
- Models, Molecular
0301 basic medicine
Virtual screening
Databases, Pharmaceutical
Computer science
General Chemical Engineering
Molecular Conformation
Computational Biology
Torsion (mechanics)
Small Molecule Libraries
General Chemistry
Library and Information Sciences
Small molecule
Molecular conformation
Computer Science Applications
03 medical and health sciences
Traffic signal
030104 developmental biology
Drug Design
Algorithm
Subjects
Details
- ISSN :
- 1549960X and 15499596
- Volume :
- 56
- Database :
- OpenAIRE
- Journal :
- Journal of Chemical Information and Modeling
- Accession number :
- edsair.doi.dedup.....19fc214f9932a8852cb5a894d3e05e6f