Structure Database (LMSD)

Common Name
Isorhamnetin
Systematic Name
3,4?,5,7-Tetrahydroxy-3?-methoxyflavone
Synonyms
  • 3-methylquercetin
LM ID
LMPK12110002
Formula
Exact Mass
Calculate m/z
316.058305
Status
Curated




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

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
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