Structure Database (LMSD)

Common Name
Ginkgetin
Systematic Name
Synonyms
  • Amentoflavone 7,4'-dimethyl ether
LM ID
LMPK12040003
Formula
Exact Mass
Calculate m/z
566.1213
Status
Curated


Classification

Biological Context

Ginkgetin is a biflavonoid that has been isolated from G. biloba and has diverse biological activities, including pro-apoptotic, antiproliferative, anti-inflammatory, anti-atherosclerosis, and neuroprotective properties.1,2,3,4 It inhibits the proliferation of OVCAR-3 ovarian and HeLa cervical cancer cells (EC50s = 3 and 5.2 μg/ml, respectively) and induces apoptosis and caspase-3 cleavage in OVCAR-3 cells when used at a concentration of 3 μg/ml.1 Topical ginkgetin (20 μg/ear) reduces ear edema and prostaglandin E2 (PGE2) levels in a mouse model of chronic skin inflammation induced by phorbol 12-myristate 13-acetate (PMA).2 It decreases the thickness of the intima-media and lipid plaque deposition in the thoracic aorta in a rat model of high-fat diet-induced atherosclerosis when administered at a dose of 100 mg/kg.3 Ginkgetin (0.8 mg/kg per day) improves sensorimotor coordination and increases the time spent on a rotating bar in a mouse model of Parkinson's disease induced by MPTP.4

This information has been provided by Cayman Chemical

References

1. Su, Y., Sun, C.M., Chuang, H.H., et al. Studies on the cytotoxic mechanisms of ginkgetin in a human ovarian adenocarcinoma cell line. Naunyn Schmiedebergs Arch. Pharmacol. 362(10), 82-90 (2000).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Ginkgo biloba (#3311)
Ginkgoopsida (#29811)
Flavonoids of Ginkgo biloba,
Ginkgo Biloba A Global Treasure, 1997

String Representations

InChiKey (Click to copy)
AIFCFBUSLAEIBR-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C32H22O10/c1-39-18-10-20(34)30-23(37)13-27(41-28(30)11-18)16-5-8-25(40-2)19(9-16)29-21(35)12-22(36)31-24(38)14-26(42-32(29)31)15-3-6-17(33)7-4-15/h3-14,33-36H,1-2H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=CC(OC)=C(C4=C(O)C=C(O)C5C(=O)C=C(C6=CC=C(O)C=C6)OC4=5)C=3)=CC(=O)C=2C(O)=C1

Other Databases

KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 42
Rings 6
Aromatic Rings 6
Rotatable Bonds 5
Van der Waals Molecular Volume 468.26
Topological Polar Surface Area 159.80
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 10
logP 7.54
Molar Refractivity 154.81

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Created at
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Updated at
8th Jun 2021