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CHEBI:65538 - cadiyenol

Default Structure
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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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