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CHEBI:69340 - ergolide

Default Structure
ChEBI IDCHEBI:69340
ChEBI Nameergolide
Stars
DefinitionA sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetyloxy group at position 4. It has been isolated from the aerial parts of Inula hupehensis.
Last Modified5 March 2020
DownloadsMolfile
FormulaC17H22O5
Net Charge0
Average Mass306.358
Monoisotopic Mass306.14672
SMILES[H][C@@]12CCC(=O)[C@@]1(C)[C@@H](OC(C)=O)[C@]1([H])C(=C)C(=O)O[C@@]1([H])C[C@H]2C
InChIInChI=1S/C17H22O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h8,11-12,14-15H,2,5-7H2,1,3-4H3/t8-,11+,12+,14-,15+,17+/m1/s1
InChIKeyJCDZXDWMCKMXFF-MMLVVLEOSA-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.
NF-kappaB inhibitor  An inhibitor of NF-κB (nuclear factor κ-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
ergolide (CHEBI:69340) has role anti-inflammatory agent (CHEBI:67079)
ergolide (CHEBI:69340) has role antineoplastic agent (CHEBI:35610)
ergolide (CHEBI:69340) has role metabolite (CHEBI:25212)
ergolide (CHEBI:69340) has role NF-κB inhibitor (CHEBI:73240)
ergolide (CHEBI:69340) has role plant metabolite (CHEBI:76924)
ergolide (CHEBI:69340) is a acetate ester (CHEBI:47622)
ergolide (CHEBI:69340) is a cyclic ketone (CHEBI:3992)
ergolide (CHEBI:69340) is a organic heterotricyclic compound (CHEBI:26979)
ergolide (CHEBI:69340) is a sesquiterpene lactone (CHEBI:37667)
ergolide (CHEBI:69340) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aR,4S,4aR,7aS,8R,9aS)-4a,8-dimethyl-3-methylidene-2,5-dioxododecahydroazuleno[6,5-b]furan-4-yl acetate
Synonym  Source
(3aR)-(3aα,4α,4aβ,7aα,8α,9aβ)-4-(acetyloxy)decahydro-4a,8-dimethyl-3-methylene-azuleno(6,5-b)furan-2,5-dioneChemIDplus
Registry NumbersSources
Reaxys:7142244Reaxys
CAS:54999-07-4ChemIDplus
Citations