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CHEBI:5638 - heliangin

ChEBI IDCHEBI:5638
ChEBI Nameheliangin
Stars
DefinitionA sesquiterpene lactone of the heliangolide group isolated from Eupatorium kiirunense and Calea rotundifolia and exhibits cytotoxicity against human oral epidermoid (KB), cervical epitheloid (Hela) and liver (hepa59T/VGH) carcinoma cells.
Secondary ChEBI IDCHEBI:65880
Last Modified28 July 2014
DownloadsMolfile
FormulaC20H26O6
Net Charge0
Average Mass362.422
Monoisotopic Mass362.17294
SMILES[H][C@@]12/C=C(\C)[C@@H](O)C[C@@]3([H])O[C@]3(C)C[C@@H](OC(=O)/C(C)=C/C)[C@@]1([H])C(=C)C(=O)O2
InChIInChI=1S/C20H26O6/c1-6-10(2)18(22)25-15-9-20(5)16(26-20)8-13(21)11(3)7-14-17(15)12(4)19(23)24-14/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6+,11-7+/t13-,14+,15+,16+,17-,20+/m0/s1
InChIKeyDZTWAOVNNLDWNH-XYXZLXRDSA-N
Species of MetaboliteComponentSourceComments
Eupatorium kiirunense (IPNI:1009045-1) - PubMed (15921421)
Calea rotundifolia (IPNI:187741-1) - DOI (10.1016/S0031-9422(00)98546-7)
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)
heliangin (CHEBI:5638) has functional parent tiglic acid (CHEBI:9592)
heliangin (CHEBI:5638) has role antineoplastic agent (CHEBI:35610)
heliangin (CHEBI:5638) has role metabolite (CHEBI:25212)
heliangin (CHEBI:5638) is a enoate ester (CHEBI:51702)
heliangin (CHEBI:5638) is a epoxide (CHEBI:32955)
heliangin (CHEBI:5638) is a sesquiterpene lactone (CHEBI:37667)
IUPAC Name 
(1aR,3S,4E,5aR,8aR,9R,10aR)-3-hydroxy-4,10a-dimethyl-8-methylidene-7-oxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydrooxireno[5,6]cyclodeca[1,2-b]furan-9-yl (2E)-2-methylbut-2-enoate
Synonym  Source
HelianginKEGG COMPOUND
Manual XrefsDatabases
C09474KEGG COMPOUND
HMDB0036692HMDB
C00000235KNApSAcK
Registry NumbersSources
Reaxys:7944517Reaxys
CAS:13323-48-3KEGG COMPOUND
Citations