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CHEBI:69348 - inuchinenolide B

ChEBI IDCHEBI:69348
ChEBI Nameinuchinenolide B
Stars
DefinitionA sesquiterpene lactone that is 3a,4,4a,5,6,7,9,9a-octahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, methyl groups at positions 5 and 8, an acetyloxy group at position 7 and a methylidene group at position 3. It has been isolated from the aerial parts of Inula hupehensis.
Last Modified18 December 2013
DownloadsMolfile
FormulaC17H22O5
Net Charge0
Average Mass306.358
Monoisotopic Mass306.14672
SMILES[H][C@@]12CC(C)=C3[C@@H](OC(C)=O)C[C@@](C)(O)[C@]3([H])C[C@]1([H])C(=C)C(=O)O2
InChIInChI=1S/C17H22O5/c1-8-5-13-11(9(2)16(19)22-13)6-12-15(8)14(21-10(3)18)7-17(12,4)20/h11-14,20H,2,5-7H2,1,3-4H3/t11-,12-,13-,14+,17-/m1/s1
InChIKeyPHMCCYUSORUPSX-MNLSVMLLSA-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:
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:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
inuchinenolide B (CHEBI:69348) has role anti-inflammatory agent (CHEBI:67079)
inuchinenolide B (CHEBI:69348) has role metabolite (CHEBI:25212)
inuchinenolide B (CHEBI:69348) has role plant metabolite (CHEBI:76924)
inuchinenolide B (CHEBI:69348) is a acetate ester (CHEBI:47622)
inuchinenolide B (CHEBI:69348) is a organic heterotricyclic compound (CHEBI:26979)
inuchinenolide B (CHEBI:69348) is a sesquiterpene lactone (CHEBI:37667)
inuchinenolide B (CHEBI:69348) is a tertiary alcohol (CHEBI:26878)
inuchinenolide B (CHEBI:69348) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aR,4aR,5R,7S,9aR)-5-hydroxy-5,8-dimethyl-3-methylidene-2-oxo-2,3,3a,4,4a,5,6,7,9,9a-decahydroazuleno[6,5-b]furan-7-yl acetate
Registry NumbersSources
Reaxys:24081613Reaxys
Citations