aromaticin (CHEBI:69335)

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ChEBI Name	aromaticin

ChEBI ID	CHEBI:69335

Definition	A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8 and a methylidene group at position 3. Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity.

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

Secondary ChEBI IDs	CHEBI:2839

Supplier Information

Download	Molfile XML SDF

Formula

C15H18O3

Net Charge

Average Mass

246.30160

Monoisotopic Mass

246.12559

InChI

InChI=1S/C15H18O3/c1-8-6-12-10(9(2)14(17)18-12)7-15(3)11(8)4-5-13(15)16/h4-5,8,10-12H,2,6-7H2,1,3H3/t8-,10-,11+,12+,15+/m1/s1

InChIKey

OSSDUQKWVVZIGP-SCGWIAOYSA-N

SMILES

C[C@@H]1C[C@@H]2OC(=O)C(=C)[C@H]2C[C@@]2(C)[C@H]1C=CC2=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):	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(s):	anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology
Outgoing	aromaticin (CHEBI:69335) has role anti-inflammatory agent (CHEBI:67079) aromaticin (CHEBI:69335) has role metabolite (CHEBI:25212) aromaticin (CHEBI:69335) has role plant metabolite (CHEBI:76924) aromaticin (CHEBI:69335) is a γ-lactone (CHEBI:37581) aromaticin (CHEBI:69335) is a cyclic ketone (CHEBI:3992) aromaticin (CHEBI:69335) is a organic heterotricyclic compound (CHEBI:26979) aromaticin (CHEBI:69335) is a sesquiterpene lactone (CHEBI:37667)

IUPAC Name

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

Synonym	Source
(3aR-(3aα,4aβ,7aα,8α,9aβ))-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno(6,5-b)furan-2,5-dione	ChemIDplus

Citation	Type	Source
21894898	PubMed citation	Europe PMC

Last Modified

28 July 2014