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CHEBI:69334 - 2α-acetoxy-4α,6α-dihydroxy-1β,5αH-guai-9(10),11(13)-dien-12,8alpha-olide

ChEBI IDCHEBI:69334
ChEBI Name2α-acetoxy-4α,6α-dihydroxy-1β,5αH-guai-9(10),11(13)-dien-12,8alpha-olide
Stars
ASCII Name2alpha-acetoxy-4alpha,6alpha-dihydroxy-1beta,5alphaH-guai-9(10),11(13)-dien-12,8alpha-olide
DefinitionA guaiane sesquiterpenoid with anti-inflammatory activity isolated from the aerial parts of Inula hupehensis.
Last Modified16 December 2013
DownloadsMolfile
FormulaC17H22O6
Net Charge0
Average Mass322.357
Monoisotopic Mass322.14164
SMILES[H][C@@]12[C@@H](O)[C@]3([H])C(=C)C(=O)O[C@@]3([H])C=C(C)[C@@]1([H])[C@@H](OC(C)=O)C[C@@]2(C)O
InChIInChI=1S/C17H22O6/c1-7-5-10-13(8(2)16(20)23-10)15(19)14-12(7)11(22-9(3)18)6-17(14,4)21/h5,10-15,19,21H,2,6H2,1,3-4H3/t10-,11-,12-,13+,14-,15-,17+/m0/s1
InChIKeyWCZBMGWSWYHCAA-PDNFSXIVSA-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 Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
2α-acetoxy-4α,6α-dihydroxy-1β,5αH-guai-9(10),11(13)-dien-12,8alpha-olide (CHEBI:69334) has role anti-inflammatory agent (CHEBI:67079)
2α-acetoxy-4α,6α-dihydroxy-1β,5αH-guai-9(10),11(13)-dien-12,8alpha-olide (CHEBI:69334) has role metabolite (CHEBI:25212)
2α-acetoxy-4α,6α-dihydroxy-1β,5αH-guai-9(10),11(13)-dien-12,8alpha-olide (CHEBI:69334) has role plant metabolite (CHEBI:76924)
2α-acetoxy-4α,6α-dihydroxy-1β,5αH-guai-9(10),11(13)-dien-12,8alpha-olide (CHEBI:69334) is a acetate ester (CHEBI:47622)
2α-acetoxy-4α,6α-dihydroxy-1β,5αH-guai-9(10),11(13)-dien-12,8alpha-olide (CHEBI:69334) is a diol (CHEBI:23824)
2α-acetoxy-4α,6α-dihydroxy-1β,5αH-guai-9(10),11(13)-dien-12,8alpha-olide (CHEBI:69334) is a guaiane sesquiterpenoid (CHEBI:36744)
2α-acetoxy-4α,6α-dihydroxy-1β,5αH-guai-9(10),11(13)-dien-12,8alpha-olide (CHEBI:69334) is a organic heterotricyclic compound (CHEBI:26979)
2α-acetoxy-4α,6α-dihydroxy-1β,5αH-guai-9(10),11(13)-dien-12,8alpha-olide (CHEBI:69334) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aS,4S,4aS,5R,7S,7aS,9aS)-4,5-dihydroxy-5,8-dimethyl-3-methylidene-2-oxo-2,3,3a,4,4a,5,6,7,7a,9a-decahydroazuleno[6,5-b]furan-7-yl acetate
Registry NumbersSources
Reaxys:21902559Reaxys
Citations