Structure Database (LMSD)
Common Name
Isorhamnetin
Systematic Name
3,4?,5,7-Tetrahydroxy-3?-methoxyflavone
Synonyms
- 3-methylquercetin
3D model of Isorhamnetin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Isorhamnetin is a natural flavonol aglycone that is the 3-methyl metabolite of quercetin . It has antioxidant activity and inhibits xanthine oxidase (IC50 = 0.40 µM).1 Isorhamnetin also competitively inhibits the human multidrug and toxic compounds extrusion transporter 1 (Ki = 0.32 µM), which has an important role in the excretion of xenobiotics at the kidney and liver.2 It has also been reported to potentiate the neurological actions of nerve growth factor, diminish the cardiotoxic impact of doxorubicin, and have beneficial anti-cancer effects.3,4,5,6
This information has been provided by Cayman Chemical
References
3. Sun, J., Sun, G., Meng, X., et al. Isorhamnetin protects against doxorubicin-induced cardiotoxicity in vivo and in vitro. PLoS One 8(5), 1-14 (2014).
4. Saud, S.M., Young, M.R., Jones-Hall, Y.L., et al. Chemopreventive activity of plant flavonoid isorhamnetin in colorectal cancer is mediated by oncogenic Src and β-catenin. Cancer Res. 73(17), 5473-5484 (2013).
5. Ramachandran, L., Manu, K.A., Shanmugam, M.K., et al. Isorhamnetin inhibits proliferation and invasion and induces apoptosis through the modulation of peroxisome proliferator-activated receptor γ activation pathway in gastric cancer. J. Biol. Chem. 287(45), 38028-38040 (2012).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Ginkgo biloba
(#3311)
Ginkgoopsida
(#29811)
Isorhamnetin, A Flavonol Aglycone from Ginkgo biloba L., Induces Neuronal Differentiation of Cultured PC12 Cells: Potentiating the Effect of Nerve Growth Factor.,
Evid Based Complement Alternat Med, 2012
Evid Based Complement Alternat Med, 2012
Pubmed ID:
22761636
String Representations
InChiKey (Click to copy)
IZQSVPBOUDKVDZ-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
SMILES (Click to copy)
C1(O)C=C2OC(C3=CC=C(O)C(OC)=C3)=C(O)C(=O)C2=C(O)C=1
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
3
Aromatic Rings
3
Rotatable Bonds
2
Van der Waals Molecular Volume
255.99
Topological Polar Surface Area
120.36
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
7
logP
3.19
Molar Refractivity
81.24
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Created at
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Updated at
23rd Jul 2024