Ononetin

Ononetin

Identifiers
IUPAC name 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone
CAS Number	487-49-0
PubChem CID	259632
ChemSpider	227880
UNII	4S084Z7YS4
ChEMBL	ChEMBL241858
CompTox Dashboard (EPA)	DTXSID50197590
Chemical and physical data
Formula	C15H14O4
Molar mass	258.273 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC=C(C=C1)CC(=O)C2=C(C=C(C=C2)O)O
InChI InChI=1S/C15H14O4/c1-19-12-5-2-10(3-6-12)8-14(17)13-7-4-11(16)9-15(13)18/h2-7,9,16,18H,8H2,1H3 Key:XHBZOAYMBBUURD-UHFFFAOYSA-N

Ononetin is a natural product from the deoxybenzoin group, which is found in the Russian traditional medicine plant Ononis spinosa . It acts as an inhibitor of the transient receptor potential ion channel TRPM3 and has analgesic effects in animal studies, ^{[1] [2]} as well as being used for research into the role of TRPM3 in the immune system dysfunction associated with chronic fatigue syndrome. ^{[3] [4]}

References

1. Straub I, Mohr F, Stab J, Konrad M, Philipp SE, Oberwinkler J, Schaefer M (April 2013). "Citrus fruit and fabacea secondary metabolites potently and selectively block TRPM3". British Journal of Pharmacology. 168 (8): 1835–50. doi:10.1111/bph.12076. PMC   3623054 . PMID   23190005.
2. Straub I, Krügel U, Mohr F, Teichert J, Rizun O, Konrad M, et al. (November 2013). "Flavanones that selectively inhibit TRPM3 attenuate thermal nociception in vivo". Molecular Pharmacology. 84 (5): 736–50. doi:10.1124/mol.113.086843. PMID   24006495. S2CID   20522738.
3. Cabanas H, Muraki K, Balinas C, Eaton-Fitch N, Staines D, Marshall-Gradisnik S (April 2019). "Validation of impaired Transient Receptor Potential Melastatin 3 ion channel activity in natural killer cells from Chronic Fatigue Syndrome/ Myalgic Encephalomyelitis patients". Molecular Medicine. 25 (1): 14. doi: 10.1186/s10020-019-0083-4 . PMC   6480905 . PMID   31014226.
4. Cabanas H, Muraki K, Staines D, Marshall-Gradisnik S (2019). "Naltrexone Restores Impaired Transient Receptor Potential Melastatin 3 Ion Channel Function in Natural Killer Cells From Myalgic Encephalomyelitis/Chronic Fatigue Syndrome Patients". Frontiers in Immunology. 10: 2545. doi: 10.3389/fimmu.2019.02545 . PMC   6834647 . PMID   31736966.