EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:65879 - eupaheliangolide A

ChEBI IDCHEBI:65879
ChEBI Nameeupaheliangolide A
Stars
DefinitionA 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.
Last Modified23 January 2013
DownloadsMolfile
FormulaC20H24O6
Net Charge0
Average Mass360.406
Monoisotopic Mass360.15729
SMILES[H][C@@]12/C=C(/C)C(=O)/C=C/[C@](C)(O)C[C@@H](OC(=O)/C(C)=C/C)[C@@]1([H])C(=C)C(=O)O2
InChIInChI=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
InChIKeyAXSMKFJOTFGINI-AWYRNCDDSA-N
Species of MetaboliteComponentSourceComments
Eupatorium kiirunense (IPNI:1009045-1) - PubMed (15921421)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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-olideChEBI
Registry NumbersSources
Reaxys:11258334Reaxys
Citations