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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24O9
Molecular Weight 408.3992
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GINKGOLIDE A

SMILES

[H][C@]12C[C@@]34[C@H]5C[C@@H](C(C)(C)C)[C@@]36[C@@H](O)C(=O)O[C@@]6([H])O[C@@]4(C(=O)O5)[C@@]1(O)[C@H](C)C(=O)O2

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

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
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
Name Type Language
GINKGOLIDE A
MI  
Common Name English
BN-52020
Common Name English
Ginkgolide A [WHO-DD]
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
Classification Tree Code System Code
DSLD 2519 (Number of products:2)
Created by admin on Sat Dec 16 05:40:21 GMT 2023 , Edited by admin on Sat Dec 16 05:40:21 GMT 2023
Code System Code Type Description
CAS
15291-75-5
Created by admin on Sat Dec 16 05:40:21 GMT 2023 , Edited by admin on Sat Dec 16 05:40:21 GMT 2023
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SMS_ID
100000170821
Created by admin on Sat Dec 16 05:40:21 GMT 2023 , Edited by admin on Sat Dec 16 05:40:21 GMT 2023
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EVMPD
SUB184977
Created by admin on Sat Dec 16 05:40:21 GMT 2023 , Edited by admin on Sat Dec 16 05:40:21 GMT 2023
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DRUG BANK
DB06743
Created by admin on Sat Dec 16 05:40:21 GMT 2023 , Edited by admin on Sat Dec 16 05:40:21 GMT 2023
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FDA UNII
TAZ2DPR77B
Created by admin on Sat Dec 16 05:40:21 GMT 2023 , Edited by admin on Sat Dec 16 05:40:21 GMT 2023
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MERCK INDEX
m5731
Created by admin on Sat Dec 16 05:40:21 GMT 2023 , Edited by admin on Sat Dec 16 05:40:21 GMT 2023
PRIMARY Merck Index
PUBCHEM
9909368
Created by admin on Sat Dec 16 05:40:21 GMT 2023 , Edited by admin on Sat Dec 16 05:40:21 GMT 2023
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EPA CompTox
DTXSID10873222
Created by admin on Sat Dec 16 05:40:21 GMT 2023 , Edited by admin on Sat Dec 16 05:40:21 GMT 2023
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