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CHEBI:138013 - Z-DEVD-FMK

ChEBI IDCHEBI:138013
ChEBI NameZ-DEVD-FMK
Stars
DefinitionA tetrapeptide consisting of Fmoc-L-aspartic acid 4-methyl ester, methyl L-α-glutamic acid 5-methyl ester, L-valine and the fluoromethyl ketone derived from the 1-carboxy group of L-aspartic acid 4-methyl ester coupled in sequence. It is a specific, irreversible caspase-3 inhibitor that also shows potent inhibition of caspase-6, caspase-7, caspase-8, and caspase-10.
Last Modified26 July 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC30H41FN4O12
Net Charge0
Average Mass668.672
Monoisotopic Mass668.27050
SMILESCOC(=O)CC[C@H](NC(=O)[C@H](CC(=O)OC)NC(=O)OCc1ccccc1)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)OC)C(=O)CF)C(C)C
InChIInChI=1S/C30H41FN4O12/c1-17(2)26(29(42)33-20(22(36)15-31)13-24(38)45-4)35-27(40)19(11-12-23(37)44-3)32-28(41)21(14-25(39)46-5)34-30(43)47-16-18-9-7-6-8-10-18/h6-10,17,19-21,26H,11-16H2,1-5H3,(H,32,41)(H,33,42)(H,34,43)(H,35,40)/t19-,20-,21-,26-/m0/s1
InChIKeyGBJVAVGBSGRRKN-JYEBCORGSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
EC 3.4.22.56 (caspase-3) inhibitor  An EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the action of caspase-3 (EC 3.4.22.56).
apoptosis inhibitor  Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
Application:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
Z-DEVD-FMK (CHEBI:138013) has role apoptosis inhibitor (CHEBI:68494)
Z-DEVD-FMK (CHEBI:138013) has role EC 3.4.22.56 (caspase-3) inhibitor (CHEBI:138014)
Z-DEVD-FMK (CHEBI:138013) has role neuroprotective agent (CHEBI:63726)
Z-DEVD-FMK (CHEBI:138013) is a tetrapeptide (CHEBI:48030)
Synonyms  Source
methyl (4S)-5-{[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino}-4-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methoxy-4-oxobutanoyl]amino}-5-oxopentanoateChEBI
N-[(phenylmethoxy)carbonyl]-L-α-aspartyl-L-α-glutamyl-N-[(1S)-3-fluoro-1-(2-methoxy-2-oxoethyl)-2-oxopropyl]-L-valinamide, 1,2-dimethyl esterChEBI
Z-Asp(OMe)-Glu(OMe)-Val-Asp(OMe)-fluoromethylketoneChEBI
benzyloxycarbonyl-Asp(OMe)-Glu(OMe)-Val-Asp(OMe)-fluoromethylketoneChEBI
specific inhibitor of caspase-3ChEBI
benzyloxycarbonyl-Asp-Glu-Val-Asp-fluoromethylketoneChEBI
Registry NumbersSources
Reaxys:9977166Reaxys
Citations