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CHEBI:5356 - ginkgolide B

ChEBI IDCHEBI:5356
ChEBI Nameginkgolide B
Stars
DefinitionA ginkgolide in which the pro-R hydrogens at positions 6, 12, and 17 of the 8-tert-butyl-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione ginkgolide skeleton have been replaced by hydroxy groups.
Last Modified2 August 2017
DownloadsMolfile
FormulaC20H24O10
Net Charge0
Average Mass424.402
Monoisotopic Mass424.13695
SMILES[H][C@@]1(C(C)(C)C)C[C@@]2([H])OC(=O)[C@@]34O[C@@H]5OC(=O)[C@H](O)C51C23[C@@H](O)[C@]1([H])OC(=O)[C@@H](C)[C@@]14O
InChIInChI=1S/C20H24O10/c1-6-12(23)28-11-9(21)18-8-5-7(16(2,3)4)17(18)10(22)13(24)29-15(17)30-20(18,14(25)27-8)19(6,11)26/h6-11,15,21-22,26H,5H2,1-4H3/t6-,7+,8-,9+,10+,11+,15+,17?,18?,19-,20-/m1/s1
InChIKeySQOJOAFXDQDRGF-NNGCZKEZSA-N
Species of MetaboliteComponentSourceComments
Ginkgo biloba (ncbitaxon:3311) root (BTO:0001188) PubMed (15038029) Isolated from root bark
Roles Classification
Biological Roles:
platelet-activating factor receptor antagonist  An antagonist that acts at the platelet-activating factor receptor.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
ginkgolide B (CHEBI:5356) has role antineoplastic agent (CHEBI:35610)
ginkgolide B (CHEBI:5356) has role neuroprotective agent (CHEBI:63726)
ginkgolide B (CHEBI:5356) has role platelet-activating factor receptor antagonist (CHEBI:134182)
ginkgolide B (CHEBI:5356) is a diterpene lactone (CHEBI:49193)
ginkgolide B (CHEBI:5356) is a ginkgolide (CHEBI:136909)
IUPAC Name 
(1R,3R,6R,8S,10R,12R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione
Manual XrefsDatabases
C07602KEGG COMPOUND
LMPR0104540002LIPID MAPS
C00035830KNApSAcK
HMDB0036861HMDB
DB06744DrugBank
Registry NumbersSources
Reaxys:4727611Reaxys
Reaxys:8173450Reaxys
CAS:15291-77-7KEGG COMPOUND
CAS:15291-77-7ChemIDplus
Citations