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CHEBI:69330 - (1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-methoxy-4-oxopseudoguai-11(13)-en-12,8-olide

ChEBI IDCHEBI:69330
ChEBI Name(1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-methoxy-4-oxopseudoguai-11(13)-en-12,8-olide
Stars
ASCII Name(1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-methoxy-4-oxopseudoguai-11(13)-en-12,8-olide
DefinitionA pseudoguaianolide with anti-inflammatory activity isolated from the aerial parts of Inula hupehensis.
Last Modified9 January 2014
DownloadsMolfile
FormulaC18H24O6
Net Charge0
Average Mass336.384
Monoisotopic Mass336.15729
SMILES[H][C@]12[C@H](C)C[C@]3([H])OC(=O)C(=C)[C@@]3([H])[C@H](OC(C)=O)[C@]1(C)C(=O)C[C@H]2OC
InChIInChI=1S/C18H24O6/c1-8-6-11-14(9(2)17(21)24-11)16(23-10(3)19)18(4)13(20)7-12(22-5)15(8)18/h8,11-12,14-16H,2,6-7H2,1,3-5H3/t8-,11+,12-,14-,15-,16+,18-/m1/s1
InChIKeyIVGBVLQEASLHGO-REDUYKFESA-N
Species of MetaboliteComponentSourceComments
Inula hupehensis (IPNI:225932-1) aerial part (BTO:0001658) PubMed (21894898) 95% aqueous EtOH extract of dried and powdered aerial parts
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
(1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-methoxy-4-oxopseudoguai-11(13)-en-12,8-olide (CHEBI:69330) has role anti-inflammatory agent (CHEBI:67079)
(1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-methoxy-4-oxopseudoguai-11(13)-en-12,8-olide (CHEBI:69330) has role plant metabolite (CHEBI:76924)
(1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-methoxy-4-oxopseudoguai-11(13)-en-12,8-olide (CHEBI:69330) is a acetate ester (CHEBI:47622)
(1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-methoxy-4-oxopseudoguai-11(13)-en-12,8-olide (CHEBI:69330) is a cyclic ketone (CHEBI:3992)
(1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-methoxy-4-oxopseudoguai-11(13)-en-12,8-olide (CHEBI:69330) is a ether (CHEBI:25698)
(1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-methoxy-4-oxopseudoguai-11(13)-en-12,8-olide (CHEBI:69330) is a organic heterotricyclic compound (CHEBI:26979)
(1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-methoxy-4-oxopseudoguai-11(13)-en-12,8-olide (CHEBI:69330) is a pseudoguaianolide (CHEBI:76704)
(1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-methoxy-4-oxopseudoguai-11(13)-en-12,8-olide (CHEBI:69330) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aR,4S,4aR,7R,7aS,8R,9aS)-7-methoxy-4a,8-dimethyl-3-methylidene-2,5-dioxododecahydroazuleno[6,5-b]furan-4-yl acetate
Registry NumbersSources
Reaxys:21902560Reaxys
Citations