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CHEBI:69338 - graveolide

Default Structure
ChEBI IDCHEBI:69338
ChEBI Namegraveolide
Stars
DefinitionA sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8 and a methylidene group at position 3. 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@@]12CCC(=O)[C@@]1(C)C[C@]1([H])C(=C)C(=O)O[C@@]1([H])C[C@H]2C
InChIInChI=1S/C15H20O3/c1-8-6-12-10(9(2)14(17)18-12)7-15(3)11(8)4-5-13(15)16/h8,10-12H,2,4-7H2,1,3H3/t8-,10-,11+,12+,15+/m1/s1
InChIKeyDCKYPAZZUYXYTC-SCGWIAOYSA-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)
graveolide (CHEBI:69338) has role anti-inflammatory agent (CHEBI:67079)
graveolide (CHEBI:69338) has role metabolite (CHEBI:25212)
graveolide (CHEBI:69338) has role plant metabolite (CHEBI:76924)
graveolide (CHEBI:69338) is a cyclic ketone (CHEBI:3992)
graveolide (CHEBI:69338) is a organic heterotricyclic compound (CHEBI:26979)
graveolide (CHEBI:69338) is a sesquiterpene lactone (CHEBI:37667)
graveolide (CHEBI:69338) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aR,4aS,7aS,8R,9aS)-4a,8-dimethyl-3-methylidenedecahydroazuleno[6,5-b]furan-2,5-dione
Registry NumbersSources
Reaxys:4785233Reaxys
Citations