The properties of fragrance molecules in the public databases SuperScent and Flavornet were analyzed to define a "fragrance-like" (FL) property range (Heavy Atom Count ≤ 21, only C, H, O, S, (O + S) ≤ 3, Hydrogen Bond Donor ≤ 1) and the corresponding chemical space including FL molecules from PubChem (NIH repository of molecules), ChEMBL (bioactive molecules), ZINC (drug-like molecules), and GDB-13 (all possible organic molecules up to 13 atoms of C, N, O, S, Cl). The FL subsets of these databases were classified by MQN (Molecular Quantum Numbers, a set of 42 integer value descriptors of molecular structure) and formatted for fast MQN-similarity searching and interactive exploration of color-coded principal component maps in form of the FL-mapplet and FL-browser applications freely available at. MQN-similarity is shown to efficiently recover 15 different fragrance molecule families from the different FL subsets, demonstrating the relevance of the MQN-based tool to explore the fragrance chemical space. © 2014 Ruddigkeit et al.; licensee Chemistry Central Ltd.
CITATION STYLE
Ruddigkeit, L., Awale, M., & Reymond, J. L. (2014). Expanding the fragrance chemical space for virtual screening. Journal of Cheminformatics, 6(1). https://doi.org/10.1186/1758-2946-6-27
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