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CHEBI:69347 - 4-epiisoinuviscolide

ChEBI IDCHEBI:69347
ChEBI Name4-epiisoinuviscolide
Stars
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 and a methylidene group at position 3 (the 3aR,4aR,5S,7aR,9aS stereoisomer). It has been isolated from the aerial parts of Inula hupehensis.
Last Modified18 December 2013
DownloadsMolfile
FormulaC15H20O3
Net Charge0
Average Mass248.322
Monoisotopic Mass248.14124
SMILES[H][C@@]12C[C@]3([H])C(=C)C(=O)O[C@@]3([H])C=C(C)[C@]1([H])CC[C@]2(C)O
InChIInChI=1S/C15H20O3/c1-8-6-13-11(9(2)14(16)18-13)7-12-10(8)4-5-15(12,3)17/h6,10-13,17H,2,4-5,7H2,1,3H3/t10-,11+,12+,13-,15-/m0/s1
InChIKeyAPMKESKZWHNIDJ-PFFFPCNUSA-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)
4-epiisoinuviscolide (CHEBI:69347) has role anti-inflammatory agent (CHEBI:67079)
4-epiisoinuviscolide (CHEBI:69347) has role metabolite (CHEBI:25212)
4-epiisoinuviscolide (CHEBI:69347) has role plant metabolite (CHEBI:76924)
4-epiisoinuviscolide (CHEBI:69347) is a organic heterotricyclic compound (CHEBI:26979)
4-epiisoinuviscolide (CHEBI:69347) is a sesquiterpene lactone (CHEBI:37667)
4-epiisoinuviscolide (CHEBI:69347) is a tertiary alcohol (CHEBI:26878)
4-epiisoinuviscolide (CHEBI:69347) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aR,4aR,5S,7aR,9aS)-5-hydroxy-5,8-dimethyl-3-methylidene-3a,4,4a,5,6,7,7a,9a-octahydroazuleno[6,5-b]furan-2(3H)-one
Registry NumbersSources
Reaxys:6512286Reaxys
Citations