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CHEBI:65538 - cadiyenol

ChEBI IDCHEBI:65538
ChEBI Namecadiyenol
Stars
DefinitionAn acetylenic compound that is (8E)-heptadeca-1,8-diene-4,6-diyne substituted by hydroxy group at positions 6 and 15, a methoxy group at position 8 and a (5-methoxy-5-oxopentyl)oxy group at position 7. Isolated from Centella asiatica, it exhibits antineoplastic activity.
Last Modified11 March 2015
DownloadsMolfile
FormulaC24H36O6
Net Charge0
Average Mass420.546
Monoisotopic Mass420.25119
SMILESC=CC(O)C#CC#C/C=C/C(OC)C(OCCCCC(=O)OC)C(O)CCCCC
InChIInChI=1S/C24H36O6/c1-5-7-10-16-21(26)24(30-19-14-13-18-23(27)29-4)22(28-3)17-12-9-8-11-15-20(25)6-2/h6,12,17,20-22,24-26H,2,5,7,10,13-14,16,18-19H2,1,3-4H3/b17-12+
InChIKeyLCCGCXCFZHBCJT-SFQUDFHCSA-N
Species of MetaboliteComponentSourceComments
Centella asiatica (ncbitaxon:48106) aerial part (BTO:0001658) PubMed (17520525)
Roles Classification
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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)
cadiyenol (CHEBI:65538) has role antineoplastic agent (CHEBI:35610)
cadiyenol (CHEBI:65538) has role apoptosis inducer (CHEBI:68495)
cadiyenol (CHEBI:65538) has role metabolite (CHEBI:25212)
cadiyenol (CHEBI:65538) is a acetylenic compound (CHEBI:73474)
cadiyenol (CHEBI:65538) is a diether (CHEBI:46786)
cadiyenol (CHEBI:65538) is a diol (CHEBI:23824)
cadiyenol (CHEBI:65538) is a methyl ester (CHEBI:25248)
cadiyenol (CHEBI:65538) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
methyl 5-{[(9E)-6,15-dihydroxy-8-methoxyheptadeca-9,16-diene-11,13-diyn-7-yl]oxy}pentanoate
Registry NumbersSources
Reaxys:11222769Reaxys
Citations