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CHEBI:69348 - inuchinenolide B

Default Structure
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:
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:
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