CHEBI:82818 - Z-Val-Phe-H

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ChEBI Name Z-Val-Phe-H
ChEBI ID CHEBI:82818
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H26N2O4
Net Charge 0
Average Mass 382.45280
Monoisotopic Mass 382.18926
InChI InChI=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
InChIKey NGBKFLTYGSREKK-PMACEKPBSA-N
SMILES CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 3.4.22.53 (calpain-2) inhibitor
A calpain inhibitor that interferes with the action of calpain-2 (EC 3.4.22.53).
EC 3.4.22.52 (calpain-1) inhibitor
A calpain inhibitor that interferes with the action of calpain-1 (EC 3.4.22.52).
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).
antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
apoptosis inhibitor
Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
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ChEBI Ontology
Outgoing Z-Val-Phe-H (CHEBI:82818) has role antileishmanial agent (CHEBI:70868)
Z-Val-Phe-H (CHEBI:82818) has role apoptosis inhibitor (CHEBI:68494)
Z-Val-Phe-H (CHEBI:82818) has role EC 3.4.22.52 (calpain-1) inhibitor (CHEBI:79050)
Z-Val-Phe-H (CHEBI:82818) has role EC 3.4.22.53 (calpain-2) inhibitor (CHEBI:82821)
Z-Val-Phe-H (CHEBI:82818) has role EC 3.4.23.46 (memapsin 2) inhibitor (CHEBI:74925)
Z-Val-Phe-H (CHEBI:82818) is a aldehyde (CHEBI:17478)
Z-Val-Phe-H (CHEBI:82818) is a carbamate ester (CHEBI:23003)
Z-Val-Phe-H (CHEBI:82818) is a dipeptide (CHEBI:46761)
IUPAC Name
benzyl [(2S)-3-methyl-1-oxo-1-{[(2S)-1-oxo-3-phenylpropan-2-yl]amino}butan-2-yl]carbamate
Synonyms Sources
calpain inhibitor III ChemIDplus
carbobenzoxyvalylphenylalanine aldehyde ChemIDplus
Cbz-Val-Phe-H ChemIDplus
L-benzyloxycarbonyl-L-valyl-L-phenylalaninal ChEBI
MDL 28,170 ChEBI
MDL 28170 ChEBI
MDL-28170 ChemIDplus
N-benzyloxycarbonylvalylphenylalaninal ChemIDplus
N-benzyloxycarbonylvalylphenylalanine aldehyde ChemIDplus
Z-Val-Phe-al ChEBI
Manual Xref Database
LSM-2958 LINCS
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Registry Numbers Types Sources
6824325 Reaxys Registry Number Reaxys
88191-84-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12001809 PubMed citation Europe PMC
15282090 PubMed citation Europe PMC
15777753 PubMed citation Europe PMC
16817871 PubMed citation Europe PMC
16842979 PubMed citation Europe PMC
17600513 PubMed citation Europe PMC
20657463 PubMed citation Europe PMC
20874056 PubMed citation Europe PMC
22253611 PubMed citation Europe PMC
22356295 PubMed citation Europe PMC
Last Modified
25 February 2016