GINKGOLIDE C

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H24O11
Molecular Weight	440.398
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1C(=O)O[C@H]2[C@H](O)[C@]34[C@@H]5OC(=O)[C@]3(O[C@@H]6OC(=O)[C@H](O)[C@]46[C@@H]([C@H]5O)C(C)(C)C)[C@@]12O

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15038029
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
platelet activating factor metabolic process 2 Target ID: GO:0046469 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2820421	Inhibitor 8504	37.6 µM [IC50]
GABA-A receptor; alpha-1/beta-2/gamma-2 28 Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15212966 \| https://www.ncbi.nlm.nih.gov/pubmed/26953225	Antagonist 2849	16.3 µM [Ki]
Platelet activating factor receptor 20 Target ID: CHEMBL250 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12570381 \| https://www.ncbi.nlm.nih.gov/pubmed/2850196	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Stroke 144 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3432553	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
GABAA receptor cysteinyl mutants and the ginkgo terpenoid lactones bilobalide and ginkgolides.	2016-04-15	26953225
Current Perspectives on the Beneficial Role of Ginkgo biloba in Neurological and Cerebrovascular Disorders.	2015	26604665
Modulation of CYP1A1 activity by a Ginkgo biloba extract in the human intestinal Caco-2 cells.	2011-05-10	21329749
Ginkgolide C inhibits platelet aggregation in cAMP- and cGMP-dependent manner by activating MMP-9.	2007-12	18057723
Restoration of impaired phosphorylation of cyclic AMP response element-binding protein (CREB) by EGb 761 and its constituents in Abeta-expressing neuroblastoma cells.	2007-11	18001288
Ginkgolides, diterpene trilactones of Ginkgo biloba, as antagonists at recombinant alpha1beta2gamma2L GABAA receptors.	2004-06-28	15212966
Chemistry and biology of terpene trilactones from Ginkgo biloba.	2004-03-19	15038029
Preparation of 7-substituted ginkgolide derivatives: potent platelet activating factor (PAF) receptor antagonists.	2003-02-13	12570381
Inhibition of the metabolism of platelet activating factor (PAF-acether) by three specific antagonists from Ginkgo biloba.	1987-09-01	2820421

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Ginkgolide C was shown to inhibit in vitro platelet aggregation at 100 µM through stimulation of matrix-metalloproteinase-9

Name

Type

Language

BN-52022

Preferred Name

English

GINKGOLIDE C

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

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

EPA CompTox

DTXSID60864569