CHEBI:65879 - eupaheliangolide A

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ChEBI Name eupaheliangolide A
ChEBI ID CHEBI:65879
Definition A sesquiterpene lactone of the heliangolide group isolated from Eupatorium kiirunense and exhibits cytotoxicity against human oral epidermoid (KB), cervical epitheloid (Hela) and liver (hepa59T/VGH) carcinoma cells.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H24O6
Net Charge 0
Average Mass 360.40100
Monoisotopic Mass 360.15729
InChI InChI=1S/C20H24O6/c1-6-11(2)18(22)26-16-10-20(5,24)8-7-14(21)12(3)9-15-17(16)13(4)19(23)25-15/h6-9,15-17,24H,4,10H2,1-3,5H3/b8-7+,11-6+,12-9-/t15-,16-,17+,20+/m1/s1
InChIKey AXSMKFJOTFGINI-AWYRNCDDSA-N
SMILES [H][C@]12OC(=O)C(=C)[C@]1([H])[C@@H](C[C@@](C)(O)\C=C\C(=O)\C(C)=C/2)OC(=O)C(\C)=C\C
Metabolite of Species Details
Eupatorium kiirunense (IPNI:1009045-1) See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing eupaheliangolide A (CHEBI:65879) has functional parent tiglic acid (CHEBI:9592)
eupaheliangolide A (CHEBI:65879) has role antineoplastic agent (CHEBI:35610)
eupaheliangolide A (CHEBI:65879) has role metabolite (CHEBI:25212)
eupaheliangolide A (CHEBI:65879) is a enoate ester (CHEBI:51702)
eupaheliangolide A (CHEBI:65879) is a enone (CHEBI:51689)
eupaheliangolide A (CHEBI:65879) is a sesquiterpene lactone (CHEBI:37667)
IUPAC Name
(3aR,4R,6R,7E,10Z,11aR)-6-hydroxy-6,10-dimethyl-3-methylidene-2,9-dioxo-2,3,3a,4,5,6,9,11a-octahydrocyclodeca[b]furan-4-yl(2E)-2-methylbut-2-enoate
Synonym Source
8β-tigloyloxy-10α-hydroxy-3-oxo-6βH,7αH-helianga-1E,4Z,11(13)-trien-6,12-olide ChEBI
Registry Number Type Source
11258334 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15921421 PubMed citation Europe PMC
Last Modified
23 January 2013