GINKGOLIDE C

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 Search

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
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 7728	37.6 µM [IC50]
GABA-A receptor; alpha-1/beta-2/gamma-2 21 Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15212966 \| https://www.ncbi.nlm.nih.gov/pubmed/26953225	Antagonist 2575	16.3 µM [Ki]
Platelet activating factor receptor 18 Target ID: CHEMBL250 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12570381 \| https://www.ncbi.nlm.nih.gov/pubmed/2850196	Antagonist 2575

Conditions

Condition	Modality	Targets	Highest Phase	Product
Stroke 138 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3432553	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibition of the metabolism of platelet activating factor (PAF-acether) by three specific antagonists from Ginkgo biloba.	1987 Sep 1	2820421
Preparation of 7-substituted ginkgolide derivatives: potent platelet activating factor (PAF) receptor antagonists.	2003 Feb 13	12570381
Ginkgolides, diterpene trilactones of Ginkgo biloba, as antagonists at recombinant alpha1beta2gamma2L GABAA receptors.	2004 Jun 28	15212966
Chemistry and biology of terpene trilactones from Ginkgo biloba.	2004 Mar 19	15038029
Ginkgolide C inhibits platelet aggregation in cAMP- and cGMP-dependent manner by activating MMP-9.	2007 Dec	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 Nov	18001288
Modulation of CYP1A1 activity by a Ginkgo biloba extract in the human intestinal Caco-2 cells.	2011 May 10	21329749
Current Perspectives on the Beneficial Role of Ginkgo biloba in Neurological and Cerebrovascular Disorders.	2015	26604665
GABAA receptor cysteinyl mutants and the ginkgo terpenoid lactones bilobalide and ginkgolides.	2016 Apr 15	26953225

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

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

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Name

Type

Language

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

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