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CHEBI:82818 - MDL-28170

Default Structure
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:
anticoronaviral agent  Any antiviral agent which inhibits the activity of coronaviruses.
EC 3.4.22.52 (calpain-1) inhibitor  A calpain inhibitor that interferes with the action of calpain-1 (EC 3.4.22.52).
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).
apoptosis inhibitor  Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 3.4.22.53 (calpain-2) inhibitor  A calpain inhibitor that interferes with the action of calpain-2 (EC 3.4.22.53).
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
calpain inhibitor IIIChemIDplus
carbobenzoxyvalylphenylalanine aldehydeChemIDplus
Cbz-Val-Phe-HChemIDplus
Cbz-Val-Phe-HChEBI
CbzValPheHChEBI
N-benzyloxycarbonyl-L-valyl-L-phenylalaninalChEBI
Manual XrefsDatabases
LSM-2958LINCS
Registry NumbersSources
Reaxys:6824325Reaxys
CAS:88191-84-8ChemIDplus
Citations