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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24O9
Molecular Weight 408.3999
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GINKGOLIDE A

SMILES

C[C@]1([H])C(=O)O[C@@]2([H])C[C@]34[C@@]5([H])C[C@@]([H])(C(C)(C)C)[C@]64[C@]([H])(C(=O)O[C@@]6([H])O[C@@]3(C(=O)O5)[C@@]12O)O

InChI

InChIKey=FPUXKXIZEIDQKW-VKMVSBOZSA-N
InChI=1S/C20H24O9/c1-7-12(22)26-10-6-17-9-5-8(16(2,3)4)18(17)11(21)13(23)28-15(18)29-20(17,14(24)27-9)19(7,10)25/h7-11,15,21,25H,5-6H2,1-4H3/t7-,8+,9-,10+,11+,15+,17-,18+,19-,20-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H24O9
Molecular Weight 408.3999
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26604665

Ginkgolide A (GA, BN52020), is a terpene lactone constituent of Ginkgo biloba, the ginkgo tree, is the oldest living tree, with a long history of use in traditional Chinese medicine. Ginkgolide A is an effective antagonist of platelet activating factor, an ubiquitous phospholipid that acts as a mediator of numerous pathophysiological conditions. Ginkgolide A displays anxiolytic, antiinflammatory properties, protects from cerebral ischemia in animal models.

CNS Activity

Curator's Comment:: Ginkgolide A is CNS active in animals, however it was reported that the compound poorly crosses the blood-brain barrier. No human data available.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Distinct role of bilobalide and ginkgolide A in the modulation of rat CYP2B1 and CYP3A23 gene expression by Ginkgo biloba extract in cultured hepatocytes.
2006 Feb
Bioactive terpenoids and flavonoids from Ginkgo biloba extract induce the expression of hepatic drug-metabolizing enzymes through pregnane X receptor, constitutive androstane receptor, and aryl hydrocarbon receptor-mediated pathways.
2009 Apr
Modulation of CYP1A1 activity by a Ginkgo biloba extract in the human intestinal Caco-2 cells.
2011 May 10
Patents

Sample Use Guides

Daily administration of ginkgolide-A in mice (1 or 2 mg/kg, po) resulted in an anxiolytic-like effect by the third treatment, with the maximal effect observed after the fifth administration. Ginkgolide A (GA, BN52020) (ED50 = 1.1 mg/kg i.v.) inhibit bronchospasms, hypotension and concomitant generation of TXA2-like activity induced by PAF-acether in anaesthetized guinea-pigs. Combined pre- and post-treatment with the Ginkgolide A (2 x 25 mg/kg, s.c.) significantly reduced the resulting neuronal damage of the CA1 and CA3 hippocampal subfields and of the occipital and parietal cerebral cortex in rat.
Route of Administration: Other
The endothelial production of high-glucose-induced interleukin (IL)-4, IL-6, IL-13 and signal transducer and activator of transcription-3 (STAT-3) phosphorylation were significantly inhibited by the pretreatment with Ginkgolide A at concentrations of 10, 15 and 20μM
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:18:25 UTC 2021
Edited
by admin
on Sat Jun 26 13:18:25 UTC 2021
Record UNII
TAZ2DPR77B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GINKGOLIDE A
MI  
Common Name English
BN-52020
Common Name English
GINKGOLIDE A [MI]
Common Name English
GINKGOLIDE A (CONSTITUENT OF GINKGO) [DSC]
Common Name English
9H-1,7A-(EPOXYMETHANO)-1H,6AH-CYCLOPENTA(C)FURO(2,3-B)FURO(3',2':3,4)CYCLOPENTA(1,2-D)FURAN-5,9,12(4H)-TRIONE, 3-(1,1-DIMETHYLETHYL)HEXAHYDRO-4,7B-DIHYDROXY-8-METHYL-, (1R,3S,3AS,4R,6AR,7AR,7BR,8S,10AS,11AS)-
Common Name English
GINKGOLIDE A [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 2519 (Number of products:2)
Created by admin on Sat Jun 26 13:18:25 UTC 2021 , Edited by admin on Sat Jun 26 13:18:25 UTC 2021
Code System Code Type Description
CAS
15291-75-5
Created by admin on Sat Jun 26 13:18:25 UTC 2021 , Edited by admin on Sat Jun 26 13:18:25 UTC 2021
PRIMARY
EVMPD
SUB184977
Created by admin on Sat Jun 26 13:18:25 UTC 2021 , Edited by admin on Sat Jun 26 13:18:25 UTC 2021
PRIMARY
DRUG BANK
DB06743
Created by admin on Sat Jun 26 13:18:25 UTC 2021 , Edited by admin on Sat Jun 26 13:18:25 UTC 2021
PRIMARY
FDA UNII
TAZ2DPR77B
Created by admin on Sat Jun 26 13:18:25 UTC 2021 , Edited by admin on Sat Jun 26 13:18:25 UTC 2021
PRIMARY
MERCK INDEX
M5731
Created by admin on Sat Jun 26 13:18:25 UTC 2021 , Edited by admin on Sat Jun 26 13:18:25 UTC 2021
PRIMARY Merck Index
PUBCHEM
9909368
Created by admin on Sat Jun 26 13:18:25 UTC 2021 , Edited by admin on Sat Jun 26 13:18:25 UTC 2021
PRIMARY
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