inuviscolide (CHEBI:69345)

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ChEBI Name	inuviscolide

ChEBI ID	CHEBI:69345

Definition	A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, a methyl group at position 5 and methylidene groups at positions 3 and 8 (the 3aR,4aR,5R,7aS,9aS stereoisomer). Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity.

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/h10-13,17H,1-2,4-7H2,3H3/t10-,11-,12-,13+,15-/m1/s1

InChIKey

GTYUWNQOOLJZBM-XLFUENPSSA-N

SMILES

C[C@@]1(O)CC[C@H]2[C@H]1C[C@H]1[C@H](CC2=C)OC(=O)C1=C

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.

Application(s):	anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology
Outgoing	inuviscolide (CHEBI:69345) has role anti-inflammatory agent (CHEBI:67079) inuviscolide (CHEBI:69345) has role plant metabolite (CHEBI:76924) inuviscolide (CHEBI:69345) is a γ-lactone (CHEBI:37581) inuviscolide (CHEBI:69345) is a organic heterotricyclic compound (CHEBI:26979) inuviscolide (CHEBI:69345) is a sesquiterpene lactone (CHEBI:37667) inuviscolide (CHEBI:69345) is a tertiary alcohol (CHEBI:26878)

IUPAC Name

(3aR,4aR,5R,7aS,9aS)-5-hydroxy-5-methyl-3,8-dimethylidenedecahydroazuleno[6,5-b]furan-2(3H)-one

Registry Number	Type	Source
4234313	Reaxys Registry Number	Reaxys

Last Modified

07 February 2022