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CHEBI:65734 - 7,8-dehydrocerberin

ChEBI IDCHEBI:65734
ChEBI Name7,8-dehydrocerberin
Stars
DefinitionA cardenolide glycoside that is the 7,8-dehydroderivative of cerberin. Isolated from Cerbera manghas, it exhibits cytotoxic activity.
Last Modified1 August 2013
DownloadsMolfile
FormulaC32H46O9
Net Charge0
Average Mass574.711
Monoisotopic Mass574.31418
SMILES[H][C@]12CC=C3[C@]([H])(CC[C@]4(C)[C@@]([H])(C5=CC(=O)OC5)CC[C@]34O)[C@@]1(C)CC[C@H](O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](OC)[C@@H]1OC(C)=O)C2
InChIInChI=1S/C32H46O9/c1-17-26(35)27(37-5)28(40-18(2)33)29(39-17)41-21-8-11-30(3)20(15-21)6-7-24-23(30)9-12-31(4)22(10-13-32(24,31)36)19-14-25(34)38-16-19/h7,14,17,20-23,26-29,35-36H,6,8-13,15-16H2,1-5H3/t17-,20+,21-,22+,23-,26-,27+,28-,29-,30-,31+,32-/m0/s1
InChIKeyMJWBKZJOFFGTCD-ZSCKLWMASA-N
Species of MetaboliteComponentSourceComments
Cerbera manghas (ncbitaxon:141545) seed (BTO:0001226) PubMed (15305009)
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.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
cardioprotective agent  Any protective agent that is able to prevent damage to the heart.
ChEBI Ontology
Outgoing Relation(s)
7,8-dehydrocerberin (CHEBI:65734) has role antineoplastic agent (CHEBI:35610)
7,8-dehydrocerberin (CHEBI:65734) has role metabolite (CHEBI:25212)
7,8-dehydrocerberin (CHEBI:65734) is a acetate ester (CHEBI:47622)
7,8-dehydrocerberin (CHEBI:65734) is a cardenolide glycoside (CHEBI:38092)
7,8-dehydrocerberin (CHEBI:65734) is a monosaccharide derivative (CHEBI:63367)
IUPAC Name 
(3β,5β)-3-[(2-O-acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxycarda-7,20(22)-dienolide
Synonym  Source
3β-O-(2'-O-acetyl-α-L-thevetosyl)-14β-hydroxy-7-en-5β-card-20(22)-enolideChEBI
Registry NumbersSources
Reaxys:9889851Reaxys
Citations