eupatolide (CHEBI:4935)

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ChEBI Name	eupatolide

ChEBI ID	CHEBI:4935

Definition	A germacranolide with formula C₁₅H₂₀O₃, isolated from several Inula species. It exhibits anti-cancer properties.

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

Supplier Information

Download	Molfile XML SDF

Formula

C15H20O3

Net Charge

Average Mass

248.322

Monoisotopic Mass

248.14124

InChI

InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h5,8,12-14,16H,3-4,6-7H2,1-2H3/b9-5+,10-8+/t12-,13-,14-/m1/s1

InChIKey

PDEJECFRCJOMEN-OURLZOILSA-N

SMILES

[H][C@]12OC(=O)C(=C)[C@]1([H])[C@H](O)C\C(C)=C\CC\C(C)=C\2

Metabolite of Species	Details
Viguiera tucumanensis (IPNI:259962-1)	See: Meragelman, K.M., Espinar, L.A., Sosa, V.E., Uriburu, M.L. and de la Fuente, J.R. (1996) Terpenoid constituents of Viguiera tucumanensis. Phytochemistry, 41(2), 499-502.
Eupatorium formosanum (NCBI:txid103749)	See: PubMed
Inula britannica (NCBI:txid119176)	Found in aerial part (BTO:0001658). See: PubMed
Inula japonica (NCBI:txid453958)	Found in flower (BTO:0000469). See: PubMed
Inula salsoloides (NCBI:txid557660)	Found in whole plant (BTO:0001461). See: Zhou, B.N., Bai, N.S., Lin, L.Z. and Cordell, G.A. (1994) Sesquiterpene lactones from Inula salsoloides. Phytochemistry, 36(3), 721-724.
Inula salsoloides (NCBI:txid557660)	Found in aerial part (BTO:0001658). See: Hu, X.J., Jin, H.Z., Liu, X.H. and Zhang, W.D. (2011) Two new sesquiterpenes from Inula salsoloides and their Inhibitory activities against NO production. Helv. Chim. Acta., 94(2), 306-312.

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):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	eupatolide (CHEBI:4935) has role antineoplastic agent (CHEBI:35610) eupatolide (CHEBI:4935) has role plant metabolite (CHEBI:76924) eupatolide (CHEBI:4935) is a γ-lactone (CHEBI:37581) eupatolide (CHEBI:4935) is a germacranolide (CHEBI:73011) eupatolide (CHEBI:4935) is a homoallylic alcohol (CHEBI:134362) eupatolide (CHEBI:4935) is a secondary alcohol (CHEBI:35681)

IUPAC Name

(3aR,4R,6E,10E,11aR)-4-hydroxy-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one

Last Modified

03 August 2020