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Expanding the fragrance chemical space for virtual screening.

ABSTRACT: 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 http://www.gdb.unibe.ch. 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.

SUBMITTER: Ruddigkeit L

PROVIDER: S-EPMC4037718 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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Expanding the fragrance chemical space for virtual screening.

Ruddigkeit Lars L Awale Mahendra M Reymond Jean-Louis JL

Journal of cheminformatics 20140522

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 databas ...[more]

PMID: 24876890

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