naringenin   Click here for help

GtoPdb Ligand ID: 10298

Synonyms: BE-14348A | naringetol
Compound class: Natural product
Comment: Naringenin is a citrus fruit flavanone. It acts as an inhibitor of TRPM3 ion channel activity [2-3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 3
Rotatable bonds 1
Topological polar surface area 86.99
Molecular weight 272.07
XLogP 2.03
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES Oc1ccc(cc1)C1CC(=O)c2c(O1)cc(cc2O)O
Isomeric SMILES Oc1ccc(cc1)C1CC(=O)c2c(O1)cc(cc2O)O
InChI InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2
InChI Key FTVWIRXFELQLPI-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

References
1. Roland WS, van Buren L, Gruppen H, Driesse M, Gouka RJ, Smit G, Vincken JP. (2013)
Bitter taste receptor activation by flavonoids and isoflavonoids: modeled structural requirements for activation of hTAS2R14 and hTAS2R39.
J Agric Food Chem, 61 (44): 10454-66. [PMID:24117141]
2. Straub I, Krügel U, Mohr F, Teichert J, Rizun O, Konrad M, Oberwinkler J, Schaefer M. (2013)
Flavanones that selectively inhibit TRPM3 attenuate thermal nociception in vivo.
Mol Pharmacol, 84 (5): 736-50. [PMID:24006495]
3. Straub I, Mohr F, Stab J, Konrad M, Philipp SE, Oberwinkler J, Schaefer M. (2013)
Citrus fruit and fabacea secondary metabolites potently and selectively block TRPM3.
Br J Pharmacol, 168 (8): 1835-50. [PMID:23190005]