ergolide (CHEBI:69340)

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ChEBI Name	ergolide

ChEBI ID	CHEBI:69340

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB5855401, ZINC000005854633

Download	Molfile XML SDF

Formula

C17H22O5

Net Charge

Average Mass

306.35360

Monoisotopic Mass

306.14672

InChI

InChI=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

InChIKey

JCDZXDWMCKMXFF-MMLVVLEOSA-N

SMILES

C[C@@H]1C[C@@H]2OC(=O)C(=C)[C@H]2[C@H](OC(C)=O)[C@@]2(C)[C@H]1CCC2=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. NF-kappaB inhibitor An inhibitor of NF-kappaB (nuclear factor kappa-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.

Application(s):	anti-inflammatory agent Any compound that has anti-inflammatory effects. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	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 γ-lactone (CHEBI:37581) 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)

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-dione	ChemIDplus

Last Modified

05 March 2020