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myricetin   Click here for help

GtoPdb Ligand ID: 13074

Synonyms: 3,3',4',5,5',7-hexahydroxyflavone | cannabiscetin
PDB Ligand
Compound class: Natural product
Comment: Myricetin is a plant-derived natural product. It is a flavonoid with a range of pharmacological activities that suggest potential therapeutic opportunities in diabetes, liver disease and cancer [2-3,5-7].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 6
Rotatable bonds 1
Topological polar surface area 147.68
Molecular weight 318.24
XLogP 1.91
No. Lipinski's rules broken 1

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 C1=C(C(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O)O)O2)O)O)O)O
Isomeric SMILES C1=C(C=C(C(=C1O)O)O)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O
InChI InChI=1S/C15H10O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,16-20,22H
InChI Key IKMDFBPHZNJCSN-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. Androutsopoulos VP, Papakyriakou A, Vourloumis D, Spandidos DA. (2011)
Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids.
Bioorg Med Chem, 19 (9): 2842-9. [PMID:21482471]
2. Babotă M, Frumuzachi O, Tanase C, Mocan A. (2024)
Efficacy of Myricetin Supplementation on Glucose and Lipid Metabolism: A Systematic Review and Meta-Analysis of In Vivo Mice Studies.
Nutrients, 16 (21). [PMID:39519561]
3. Chen M, Zhang S, Huang X, Zhang D, Zhu D, Ouyang C, Li Y. (2025)
The protective effects and mechanism of myricetin in liver diseases (Review).
Mol Med Rep, 31 (4). [PMID:39917997]
4. Hagiwara M, Inoue S, Tanaka T, Nunoki K, Ito M, Hidaka H. (1988)
Differential effects of flavonoids as inhibitors of tyrosine protein kinases and serine/threonine protein kinases.
Biochem Pharmacol, 37 (15): 2987-92. [PMID:3164998]
5. Oldoni TLC, da Silva C, Bicas TC, Ayres BRB, Zanchet ER, Marafon F, da Silva AP, Carpes ST, Bagatini MD, Ascari J et al.. (2025)
Antihyperglycemic activity and bioguided isolation of phenolic compounds with antioxidant and cytotoxic properties from Syzygium malaccense leaves.
Fitoterapia, 181: 106357. [PMID:39732206]
6. Pattanaik SK, Anil MP, Jena S, Rath D. (2024)
A Mechanism-based Perspective on the Use of Flavonoids in the Treatment of Diabetes and its Complications.
Curr Diabetes Rev, [Epub ahead of print]. [PMID:39620338]
7. Phosrithong N, Ungwitayatorn J. (2010)
Molecular docking study on anticancer activity of plant-derived natural products.
Med Chem Res, 19: 817–835. DOI: 10.1007/s00044-009-9233-5
8. Williams LK, Li C, Withers SG, Brayer GD. (2012)
Order and disorder: differential structural impacts of myricetin and ethyl caffeate on human amylase, an antidiabetic target.
J Med Chem, 55 (22): 10177-86. [PMID:23050660]