CHEBI:5638 - heliangin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name heliangin
ChEBI ID CHEBI:5638
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:65880
Supplier Information
Download Molfile XML SDF
Formula C20H26O6
Net Charge 0
Average Mass 362.41680
Monoisotopic Mass 362.173
InChI InChI=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
InChIKey DZTWAOVNNLDWNH-XYXZLXRDSA-N
SMILES [H][C@@]12C[C@H](O)\C(C)=C\[C@@]3([H])OC(=O)C(=C)[C@]3([H])[C@@H](C[C@@]1(C)O2)OC(=O)C(\C)=C\C
Metabolite of Species Details
Eupatorium kiirunense (IPNI:1009045-1) See: PubMed
Calea rotundifolia (IPNI:187741-1) See: DOI
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 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
Heliangin KEGG COMPOUND
Manual Xrefs Databases
C00000235 KNApSAcK
C09474 KEGG COMPOUND
HMDB0036692 HMDB
View more database links
Registry Numbers Types Sources
13323-48-3 CAS Registry Number KEGG COMPOUND
7944517 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15921421 PubMed citation Europe PMC
Last Modified
28 July 2014