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CHEBI:82818 - MDL-28170

ChEBI IDCHEBI:82818
ChEBI NameMDL-28170
Stars
DefinitionA dipeptide resulting from the formal condensation of the carboxy group of N-benzyloxycarbonyl-L-valine with the amino group of L-phenylalanine aldehyde. It is a potent cell-permeable inhibitor of calpain I and II, and is also a γ-secretase inhibitor.
Last Modified28 February 2025
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H26N2O4
Net Charge0
Average Mass382.460
Monoisotopic Mass382.18926
SMILES[H]C(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C
InChIInChI=1S/C22H26N2O4/c1-16(2)20(24-22(27)28-15-18-11-7-4-8-12-18)21(26)23-19(14-25)13-17-9-5-3-6-10-17/h3-12,14,16,19-20H,13,15H2,1-2H3,(H,23,26)(H,24,27)/t19-,20-/m0/s1
InChIKeyNGBKFLTYGSREKK-PMACEKPBSA-N
Roles Classification
Biological Roles:
EC 3.4.22.53 (calpain-2) inhibitor  A calpain inhibitor that interferes with the action of calpain-2 (EC 3.4.22.53).
apoptosis inhibitor  Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 3.4.22.52 (calpain-1) inhibitor  A calpain inhibitor that interferes with the action of calpain-1 (EC 3.4.22.52).
anticoronaviral agent  Any antiviral agent which inhibits the activity of coronaviruses.
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
EC 3.4.23.46 (memapsin 2) inhibitor  An EC 3.4.23.* (aspartic endopeptidase) inhibitor that interferes with the activity of memapsin 2 (EC 3.4.23.46).
Application:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
ChEBI Ontology
Outgoing Relation(s)
MDL-28170 (CHEBI:82818) has role anticoronaviral agent (CHEBI:149553)
MDL-28170 (CHEBI:82818) has role antileishmanial agent (CHEBI:70868)
MDL-28170 (CHEBI:82818) has role apoptosis inhibitor (CHEBI:68494)
MDL-28170 (CHEBI:82818) has role EC 3.4.22.52 (calpain-1) inhibitor (CHEBI:79050)
MDL-28170 (CHEBI:82818) has role EC 3.4.22.53 (calpain-2) inhibitor (CHEBI:82821)
MDL-28170 (CHEBI:82818) has role EC 3.4.23.46 (memapsin 2) inhibitor (CHEBI:74925)
MDL-28170 (CHEBI:82818) is a aldehyde (CHEBI:17478)
MDL-28170 (CHEBI:82818) is a carbamate ester (CHEBI:23003)
MDL-28170 (CHEBI:82818) is a secondary carboxamide (CHEBI:140325)
IUPAC Name 
benzyl [(2S)-3-methyl-1-oxo-1-{[(2S)-1-oxo-3-phenylpropan-2-yl]amino}butan-2-yl]carbamate
Synonyms  Source
carbobenzoxyvalylphenylalanine aldehydeChemIDplus
Cbz-Val-Phe-HChemIDplus
L-benzyloxycarbonyl-L-valyl-L-phenylalaninalChEBI
calpain inhibitor IIIChemIDplus
N-benzyloxycarbonylvalylphenylalanine aldehydeChemIDplus
N-benzyloxycarbonylvalylphenylalaninalChemIDplus
Manual XrefsDatabases
LSM-2958LINCS
Registry NumbersSources
Reaxys:6824325Reaxys
CAS:88191-84-8ChemIDplus
Citations