4-epiisoinuviscolide (CHEBI:69347)

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ChEBI Name	4-epiisoinuviscolide

ChEBI ID	CHEBI:69347

Definition	A sesquiterpene lactone that is 3a,4,4a,5,6,7,7a,9a-octahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, methyl groups at positions 5 and 8 and a methylidene group at position 3 (the 3aR,4aR,5S,7aR,9aS stereoisomer). 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/c1-8-6-13-11(9(2)14(16)18-13)7-12-10(8)4-5-15(12,3)17/h6,10-13,17H,2,4-5,7H2,1,3H3/t10-,11+,12+,13-,15-/m0/s1

InChIKey

APMKESKZWHNIDJ-PFFFPCNUSA-N

SMILES

CC1=C[C@@H]2OC(=O)C(=C)[C@H]2C[C@@H]2[C@H]1CC[C@]2(C)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	4-epiisoinuviscolide (CHEBI:69347) has role anti-inflammatory agent (CHEBI:67079) 4-epiisoinuviscolide (CHEBI:69347) has role metabolite (CHEBI:25212) 4-epiisoinuviscolide (CHEBI:69347) has role plant metabolite (CHEBI:76924) 4-epiisoinuviscolide (CHEBI:69347) is a γ-lactone (CHEBI:37581) 4-epiisoinuviscolide (CHEBI:69347) is a organic heterotricyclic compound (CHEBI:26979) 4-epiisoinuviscolide (CHEBI:69347) is a sesquiterpene lactone (CHEBI:37667) 4-epiisoinuviscolide (CHEBI:69347) is a tertiary alcohol (CHEBI:26878)

IUPAC Name

(3aR,4aR,5S,7aR,9aS)-5-hydroxy-5,8-dimethyl-3-methylidene-3a,4,4a,5,6,7,7a,9a-octahydroazuleno[6,5-b]furan-2(3H)-one

Registry Number	Type	Source
6512286	Reaxys Registry Number	Reaxys

Citation	Type	Source
21894898	PubMed citation	Europe PMC

Last Modified

18 December 2013