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

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ChEBI Name 2α-acetoxy-4α,6α-dihydroxy-1β,5αH-guai-9(10),11(13)-dien-12,8alpha-olide
ChEBI ID CHEBI:69334
ChEBI ASCII Name 2alpha-acetoxy-4alpha,6alpha-dihydroxy-1beta,5alphaH-guai-9(10),11(13)-dien-12,8alpha-olide
Definition A guaiane sesquiterpenoid with anti-inflammatory activity isolated from the aerial parts of Inula hupehensis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C17H22O6
Net Charge 0
Average Mass 322.35300
Monoisotopic Mass 322.14164
InChI InChI=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
InChIKey WCZBMGWSWYHCAA-PDNFSXIVSA-N
SMILES CC(=O)O[C@H]1C[C@@](C)(O)[C@H]2[C@H]1C(C)=C[C@@H]1OC(=O)C(=C)[C@H]1[C@@H]2O
Metabolite of Species Details
Inula hupehensis (IPNI:225932-1) Found in aerial part (BTO:0001658). 95% aqueous EtOH extract of dried and powdered aerial parts See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 γ-lactone (CHEBI:37581)
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)
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 Number Type Source
21902559 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21894898 PubMed citation Europe PMC
Last Modified
16 December 2013