graveolide (CHEBI:69338)

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ChEBI Name	graveolide

ChEBI ID	CHEBI:69338

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C15H20O3

Net Charge

Average Mass

248.31750

Monoisotopic Mass

248.14124

InChI

InChI=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

InChIKey

DCKYPAZZUYXYTC-SCGWIAOYSA-N

SMILES

C[C@@H]1C[C@@H]2OC(=O)C(=C)[C@H]2C[C@@]2(C)[C@H]1CCC2=O

Metabolite of Species	Details
Inula hupehensis (IPNI:225932-1)	Found in aerial part (BTO:0001658). 95% aqueous EtOH extract of dried and powdered aerial parts See: PubMed

Roles Classification
Biological Role(s):	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(s):	anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology
Outgoing	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 γ-lactone (CHEBI:37581) 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)

IUPAC Name

(3aR,4aS,7aS,8R,9aS)-4a,8-dimethyl-3-methylidenedecahydroazuleno[6,5-b]furan-2,5-dione

Registry Number	Type	Source
4785233	Reaxys Registry Number	Reaxys

Citation	Type	Source
21894898	PubMed citation	Europe PMC

Last Modified

18 December 2013