U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24O11
Molecular Weight 440.3988
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GINKGOLIDE C

SMILES

C[C@]1([H])C(=O)O[C@@]2([H])[C@@]([H])([C@]34[C@@]5([H])[C@@]([H])([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)O)O

InChI

InChIKey=AMOGMTLMADGEOQ-DTDWCABLSA-N
InChI=1S/C20H24O11/c1-5-12(24)28-11-8(22)18-10-6(21)7(16(2,3)4)17(18)9(23)13(25)30-15(17)31-20(18,14(26)29-10)19(5,11)27/h5-11,15,21-23,27H,1-4H3/t5-,6-,7+,8+,9+,10-,11+,15+,17+,18-,19-,20-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H24O11
Molecular Weight 440.3988
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 12 / 12
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 C (GC, BN52022), 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 C is 25-fold less potent than ginkgolide B as a platelet activating factor receptor antagonist, due to the presence of the 7beta-OH. Ginkgolide C may not be bioavailable at clinically relevant concentrations due to rapid metabolism.

CNS Activity

Curator's Comment:: Ginkgolide C is CNS active in animals. No human data available.

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibition of the metabolism of platelet activating factor (PAF-acether) by three specific antagonists from Ginkgo biloba.
1987 Sep 1
Preparation of 7-substituted ginkgolide derivatives: potent platelet activating factor (PAF) receptor antagonists.
2003 Feb 13
Ginkgolides, diterpene trilactones of Ginkgo biloba, as antagonists at recombinant alpha1beta2gamma2L GABAA receptors.
2004 Jun 28
Chemistry and biology of terpene trilactones from Ginkgo biloba.
2004 Mar 19
Ginkgolide C inhibits platelet aggregation in cAMP- and cGMP-dependent manner by activating MMP-9.
2007 Dec
Restoration of impaired phosphorylation of cyclic AMP response element-binding protein (CREB) by EGb 761 and its constituents in Abeta-expressing neuroblastoma cells.
2007 Nov
Modulation of CYP1A1 activity by a Ginkgo biloba extract in the human intestinal Caco-2 cells.
2011 May 10
Current Perspectives on the Beneficial Role of Ginkgo biloba in Neurological and Cerebrovascular Disorders.
2015
GABAA receptor cysteinyl mutants and the ginkgo terpenoid lactones bilobalide and ginkgolides.
2016 Apr 15
Patents

Sample Use Guides

Unknown
Route of Administration: Unknown
Ginkgolide C was shown to inhibit in vitro platelet aggregation at 100 µM through stimulation of matrix-metalloproteinase-9
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:20:32 UTC 2021
Edited
by admin
on Sat Jun 26 16:20:32 UTC 2021
Record UNII
32ZQ957R4A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GINKGOLIDE C
MI  
Common Name English
GINKGOLIDE C (CONSTITUENT OF GINKGO) [DSC]
Common Name English
GINKGOLIDE C [MI]
Common Name English
(1.ALPHA.,7.BETA.)-1,7-DIHYDROXYGINKGOLIDE A
Common Name English
BN-52022
Code 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-2,4,7B,11-TETRAHYDROXY-8-METHYL-, (1S,2R,3S,3AS,4R,6AR,7AR,7BR,8S,10AS,11R,11AR)-
Common Name English
GINKGOLIDE C [WHO-DD]
Common Name English
Code System Code Type Description
MESH
C058295
Created by admin on Sat Jun 26 16:20:32 UTC 2021 , Edited by admin on Sat Jun 26 16:20:32 UTC 2021
PRIMARY
CAS
15291-76-6
Created by admin on Sat Jun 26 16:20:32 UTC 2021 , Edited by admin on Sat Jun 26 16:20:32 UTC 2021
PRIMARY
FDA UNII
32ZQ957R4A
Created by admin on Sat Jun 26 16:20:32 UTC 2021 , Edited by admin on Sat Jun 26 16:20:32 UTC 2021
PRIMARY
EVMPD
SUB184979
Created by admin on Sat Jun 26 16:20:32 UTC 2021 , Edited by admin on Sat Jun 26 16:20:32 UTC 2021
PRIMARY
DRUG BANK
DB06745
Created by admin on Sat Jun 26 16:20:32 UTC 2021 , Edited by admin on Sat Jun 26 16:20:32 UTC 2021
PRIMARY
MERCK INDEX
M5731
Created by admin on Sat Jun 26 16:20:32 UTC 2021 , Edited by admin on Sat Jun 26 16:20:32 UTC 2021
PRIMARY Merck Index
PUBCHEM
9867869
Created by admin on Sat Jun 26 16:20:32 UTC 2021 , Edited by admin on Sat Jun 26 16:20:32 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
USP