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CHEBI:69336 - 8-epihelenalin

Default Structure
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:
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)
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