CHEBI:65538 - cadiyenol

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name cadiyenol
ChEBI ID CHEBI:65538
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C24H36O6
Net Charge 0
Average Mass 420.53900
Monoisotopic Mass 420.25119
InChI InChI=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+
InChIKey LCCGCXCFZHBCJT-SFQUDFHCSA-N
SMILES CCCCCC(O)C(OCCCCC(=O)OC)C(OC)\C=C\C#CC#CC(O)C=C
Metabolite of Species Details
Centella asiatica (NCBI:txid48106) Found in aerial part (BTO:0001658). See: PubMed
Roles Classification
Biological Role(s): 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(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
11222769 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17520525 PubMed citation Europe PMC
Last Modified
11 March 2015