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CHEBI:69341 - 6α-acetoxyisoinuviscolide

Default Structure
ChEBI IDCHEBI:69341
ChEBI Name6α-acetoxyisoinuviscolide
Stars
ASCII Name6alpha-acetoxyisoinuviscolide
DefinitionA sesquiterpene lactone that is 3a,4,4a,5,6,7,7a,9a-octahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, methyl groups at positions 5 and 8, a methylidene group at position 3 and an acetoxy group at position 4. It has been isolated from the aerial parts of Inula hupehensis.
Last Modified18 December 2013
DownloadsMolfile
FormulaC17H22O5
Net Charge0
Average Mass306.358
Monoisotopic Mass306.14672
SMILES[H][C@@]12[C@@H](OC(C)=O)[C@]3([H])C(=C)C(=O)O[C@@]3([H])C=C(C)[C@@]1([H])CC[C@@]2(C)O
InChIInChI=1S/C17H22O5/c1-8-7-12-13(9(2)16(19)22-12)15(21-10(3)18)14-11(8)5-6-17(14,4)20/h7,11-15,20H,2,5-6H2,1,3-4H3/t11-,12+,13-,14+,15+,17-/m1/s1
InChIKeyPLSCGWSBZMOKAA-RURKYGKJSA-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:
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.
ChEBI Ontology
Outgoing Relation(s)
6α-acetoxyisoinuviscolide (CHEBI:69341) has role metabolite (CHEBI:25212)
6α-acetoxyisoinuviscolide (CHEBI:69341) has role plant metabolite (CHEBI:76924)
6α-acetoxyisoinuviscolide (CHEBI:69341) is a acetate ester (CHEBI:47622)
6α-acetoxyisoinuviscolide (CHEBI:69341) is a organic heterotricyclic compound (CHEBI:26979)
6α-acetoxyisoinuviscolide (CHEBI:69341) is a sesquiterpene lactone (CHEBI:37667)
6α-acetoxyisoinuviscolide (CHEBI:69341) is a tertiary alcohol (CHEBI:26878)
6α-acetoxyisoinuviscolide (CHEBI:69341) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aR,4S,4aS,5R,7aS,9aS)-5-hydroxy-5,8-dimethyl-3-methylidene-2-oxo-2,3,3a,4,4a,5,6,7,7a,9a-decahydroazuleno[6,5-b]furan-4-yl acetate
Citations