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
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
| Molecular Formula | C20H24O9 |
| Molecular Weight | 408.3992 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 9 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26604665
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26604665 | https://www.ncbi.nlm.nih.gov/pubmed/27182682
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0046469 |
9.7 µM [IC50] | ||
Target ID: CHEMBL2095172 |
14.5 µM [Ki] | ||
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Ginkgolide A, B, and huperzine A inhibit nitric oxide-induced neurotoxicity. | 2002 Oct |
|
| Ginkgolide A contributes to the potentiation of acetaminophen toxicity by Ginkgo biloba extract in primary cultures of rat hepatocytes. | 2006 Dec 1 |
|
| 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 |
|
| Induction of cytochrome P450s by terpene trilactones and flavonoids of the Ginkgo biloba extract EGb 761 in rats. | 2008 May |
|
| 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
| Substance Class |
Chemical
Created
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admin
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Edited
Sat Dec 16 05:40:21 UTC 2023
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Sat Dec 16 05:40:21 UTC 2023
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TAZ2DPR77B
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| Record Status |
Validated (UNII)
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2519 (Number of products:2)
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DB06743
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TAZ2DPR77B
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m5731
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DTXSID10873222
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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