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CHEBI:69336 - 8-epihelenalin

ChEBI IDCHEBI:69336
ChEBI Name8-epihelenalin
Stars
DefinitionA sesquiterpene lactone that is the C-8 epimer of helenalin. Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity.
Last Modified16 December 2013
DownloadsMolfile
FormulaC15H18O4
Net Charge0
Average Mass262.305
Monoisotopic Mass262.12051
SMILES[H][C@@]12C=CC(=O)[C@@]1(C)[C@@H](O)[C@]1([H])C(=C)C(=O)O[C@@]1([H])C[C@H]2C
InChIInChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10+,12-,13+,15+/m1/s1
InChIKeyZVLOPMNVFLSSAA-GSNHZRAGSA-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)
8-epihelenalin (CHEBI:69336) has role anti-inflammatory agent (CHEBI:67079)
8-epihelenalin (CHEBI:69336) has role metabolite (CHEBI:25212)
8-epihelenalin (CHEBI:69336) has role plant metabolite (CHEBI:76924)
8-epihelenalin (CHEBI:69336) is a cyclic ketone (CHEBI:3992)
8-epihelenalin (CHEBI:69336) is a organic heterotricyclic compound (CHEBI:26979)
8-epihelenalin (CHEBI:69336) is a secondary alcohol (CHEBI:35681)
8-epihelenalin (CHEBI:69336) is a sesquiterpene lactone (CHEBI:37667)
8-epihelenalin (CHEBI:69336) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aS,4S,4aR,7aR,8R,9aS)-4-hydroxy-4a,8-dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
Registry NumbersSources
Reaxys:1291189Reaxys
Citations