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CHEBI:69347 - 4-epiisoinuviscolide

Default Structure
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:
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:
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