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HPLC Coupled with Chemical Fingerprinting for Multi-Pattern Recognition for Identifying the Authenticity of Clematidis Armandii Caulis
Published on: November 11, 2022
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One chiral fingerprint to find them all
Markus Orsi1, Jean-Louis Reymond2
1Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern, Freiestrasse 3, 3012, Bern, Switzerland.
Journal of Cheminformatics
|May 14, 2024
Summary
A new chiral molecular fingerprint, MAP4C, accurately accounts for stereochemistry in molecules. This advancement improves virtual screening and distinguishes stereoisomers across diverse chemical structures, from drugs to peptides.
Area of Science:
- Cheminformatics and computational chemistry.
- Development of novel molecular descriptors.
Background:
- Traditional molecular fingerprints often neglect stereochemistry, a critical feature for chiral molecules.
- This limitation is particularly problematic for large molecules, which are frequently chiral.
Purpose of the Study:
- To introduce MAP4C, a chiral molecular fingerprint designed to incorporate stereochemical information.
- To evaluate MAP4C's performance in distinguishing stereoisomers and its utility in virtual screening.
Main Methods:
- MAP4C is based on MinHashes of character strings representing pairs of circular substructures up to a four-bond diameter.
- It incorporates Cahn-Ingold-Prelog (CIP) annotations for stereocenters and cis-trans information for double bonds.
Main Results:
- MAP4C demonstrates slightly improved performance over achiral fingerprints (MAP4, ECFP, AP) in non-stereoselective virtual screening.
- MAP4C effectively distinguishes between stereoisomers in a wide range of molecules, including drugs, natural products, and peptides.
- The degree of distinction is proportional to the number of chirality changes and smaller than that between structural isomers.
Conclusions:
- MAP4C is a generally applicable chiral molecular fingerprint capable of handling stereochemistry across diverse molecular classes.
- Its ability to differentiate stereoisomers is unprecedented, paving the way for stereochemistry's integration as a key molecular parameter in molecular design.
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