Structure Database (LMSD)

Common Name
Myricetin
Systematic Name
3,3?,4?,5,5?,7-Hexahydroxyflavone
Synonyms
  • Cannabiscetin
  • Myricetol
  • Myricitin
LM ID
LMPK12110001
Formula
C15H10O8
Exact Mass
Calculate m/z
318.03757
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum
View ion mobility data

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Flavones and Flavonols [PK1211]

Biological Context

Myricetin is a flavonoid compound found in many fruits and vegetables, including red wine, that acts as a powerful antioxidant.1 Myricetin inhibits TBARS formation with an IC50 value of 6.34 and at 20 µM, blocks oxLDL uptake by U937-derived macrophages, reducing CD36 expression.2 Myricetin demonstrates potent chemopreventative potential by binding JAK1/STAT3 to inhibit the neoplastic transformation of murine JB6 P+ cells and inhibiting MEK1 kinase activity.3,4

This information has been provided by Cayman Chemical

References

1. Lee, K.W., Kang, N.J., Rogozin, E.A., et al. Myricetin is a novel natural inhibitor of neoplastic cell transformation and MEK1. Carcinogenesis 28(9), 1918-1927 (2007).
2. Kumamoto, T., Fujii, M., and Hou, D.X. Myricetin directly targets JAK1 to inhibit cell transformation. Cancer Lett. 275(1), 17-26 (2009).
3. Lian, T.-W., Wang, L., Lo, Y.-H., et al. Fisetin, morin and myricetin attenuate CD36 expression and oxLDL uptake in U937-derived macrophages. Biochim. Biophys. Acta 1781(10), 601-609 (2008).
4. Bennett, C.J., Caldwell, S.T., McPhail, D.B., et al. Potential therapeutic antioxidants that combine the radical scavenging ability of myricetin and the lipophilic chain of vitamin E to effectively inhibit microsomal lipid peroxidation. Bioorg. Med. Chem. 12(9), 2079-2098 (2004).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Morella rubra (#262757)
Magnoliopsida (#3398)
Anti-inflammatory activity of myricetin isolated from Myrica rubra Sieb. et Zucc. leaves.,
Planta Med, 2010
Pubmed ID: 20383816

String Representations

InChiKey (Click to copy)
IKMDFBPHZNJCSN-UHFFFAOYSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1(O)C=C2OC(C3=CC(O)=C(O)C(O)=C3)=C(O)C(=O)C2=C(O)C=1

Other Databases

Wikipedia
Myricetin
KEGG ID
C10107
HMDB ID
HMDB0002755
CHEBI ID
18152
PubChem CID
5281672
Cayman ID
10012600
PDB ID
MYC
GuidePharm ID
13074

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 3
Aromatic Rings 3
Rotatable Bonds 1
Van der Waals Molecular Volume 247.48
Topological Polar Surface Area 151.59
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 8
logP 2.59
Molar Refractivity 78.02

Admin

Created at
-
Updated at
3rd Apr 2025