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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:Z-Val-Phe-H
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Accession:CHEBI:82818 term browser browse the term
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 gamma-secretase inhibitor.
Synonyms:exact_synonym: benzyl [(2S)-3-methyl-1-oxo-1-{[(2S)-1-oxo-3-phenylpropan-2-yl]amino}butan-2-yl]carbamate
 related_synonym: Cbz-Val-Phe-H;   Formula=C22H26N2O4;   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;   L-benzyloxycarbonyl-L-valyl-L-phenylalaninal;   MDL 28,170;   MDL 28170;   N-benzyloxycarbonylvalylphenylalaninal;   N-benzyloxycarbonylvalylphenylalanine aldehyde;   SMILES=CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C=O;   Z-Val-Phe-al;   calpain inhibitor III;   carbobenzoxyvalylphenylalanine aldehyde
 xref: CAS:88191-84-8;   LINCS:LSM-2958
 xref_mesh: MESH:C058076
 xref: PMID:12001809;   PMID:15282090;   PMID:15777753;   PMID:16817871;   PMID:16842979;   PMID:17600513;   PMID:20657463;   PMID:20874056;   PMID:22253611;   PMID:22356295;   Reaxys:6824325


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Z-Val-Phe-H term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G AHR aryl hydrocarbon receptor multiple interactions EXP calpain inhibitor III inhibits the reaction [Tetrachlorodibenzodioxin results in increased degradation of AHR protein] CTD PMID:16891617 NCBI chr 7:17,298,652...17,346,147
Ensembl chr 7:16,916,359...17,346,152
JBrowse link
G AIFM1 apoptosis inducing factor mitochondria associated 1 multiple interactions ISO calpain inhibitor III inhibits the reaction [Isoflurane results in increased cleavage of and affects the localization of AIFM1 protein] CTD PMID:29289695 NCBI chr  X:130,129,362...130,165,841
Ensembl chr  X:130,124,666...130,165,879
JBrowse link
G CAPN1 calpain 1 multiple interactions
decreases activity
EXP
ISO
calpain inhibitor III inhibits the reaction [CAPN1 protein results in increased susceptibility to Cisplatin]
calpain inhibitor III inhibits the reaction [Calcium results in increased activity of CAPN1 protein]; calpain inhibitor III inhibits the reaction [Carbon Tetrachloride results in increased expression of and results in increased activity of CAPN1 protein]; calpain inhibitor III inhibits the reaction [Isoflurane results in increased expression of CAPN1 protein]; calpain inhibitor III inhibits the reaction [Manganese results in increased activity of CAPN1 protein]
calpain inhibitor III results in decreased activity of CAPN1 protein
CTD PMID:13678654 PMID:20878076 PMID:21985864 PMID:29289695 NCBI chr11:65,181,373...65,212,006
Ensembl chr11:65,180,566...65,212,006
JBrowse link
G CAPN2 calpain 2 multiple interactions ISO calpain inhibitor III inhibits the reaction [Isoflurane results in increased expression of CAPN2 protein] CTD PMID:29289695 NCBI chr 1:223,701,597...223,776,018
Ensembl chr 1:223,701,593...223,776,018
JBrowse link
G CYP1A1 cytochrome P450 family 1 subfamily A member 1 multiple interactions EXP calpain inhibitor III inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of CYP1A1 mRNA] CTD PMID:16891617 NCBI chr15:74,719,542...74,725,528
Ensembl chr15:74,719,542...74,725,536
JBrowse link
G HSPA5 heat shock protein family A (Hsp70) member 5 multiple interactions ISO calpain inhibitor III inhibits the reaction [deoxynivalenol results in increased degradation of HSPA5 protein] CTD PMID:19336499 NCBI chr 9:125,234,853...125,241,343
Ensembl chr 9:125,234,853...125,241,382
JBrowse link
G IL1A interleukin 1 alpha affects localization EXP calpain inhibitor III affects the localization of IL1A protein CTD PMID:24024155 NCBI chr 2:112,773,925...112,784,493
Ensembl chr 2:112,773,925...112,784,493
JBrowse link
G NEFL neurofilament light chain multiple interactions ISO calpain inhibitor III inhibits the reaction [Zymosan results in increased degradation of NEFL protein] CTD PMID:15275793 NCBI chr 8:24,950,955...24,956,612
Ensembl chr 8:24,950,955...24,956,721
JBrowse link
G NOS2 nitric oxide synthase 2 multiple interactions ISO calpain inhibitor III inhibits the reaction [Thioacetamide results in increased expression of NOS2 mRNA] CTD PMID:15316131 NCBI chr17:27,756,766...27,800,529
Ensembl chr17:27,756,766...27,800,529
JBrowse link
G SPTAN1 spectrin alpha, non-erythrocytic 1 multiple interactions ISO calpain inhibitor III inhibits the reaction [lactacystin results in increased cleavage of SPTAN1 protein]
calpain inhibitor III inhibits the reaction [Manganese results in increased cleavage of SPTAN1 protein]
CTD PMID:21683092 PMID:21985864 NCBI chr 9:128,552,564...128,633,662
Ensembl chr 9:128,552,558...128,633,662
JBrowse link
G TNF tumor necrosis factor multiple interactions ISO calpain inhibitor III inhibits the reaction [Thioacetamide results in increased expression of TNF mRNA] CTD PMID:15316131 NCBI chr 6:31,575,565...31,578,336
Ensembl chr 6:31,575,565...31,578,336
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 24775
    role 24693
      biological role 24662
        inhibitor 21475
          apoptosis inhibitor 6954
            Z-Val-Phe-H 11
Path 2
Term Annotations click to browse term
  CHEBI ontology 24775
    subatomic particle 24735
      composite particle 24735
        hadron 24735
          baryon 24735
            nucleon 24735
              atomic nucleus 24735
                atom 24735
                  main group element atom 24601
                    p-block element atom 24601
                      carbon group element atom 24393
                        carbon atom 24357
                          organic molecular entity 24357
                            organic group 22763
                              organic divalent group 22742
                                organodiyl group 22742
                                  carbonyl group 22729
                                    carbonyl compound 22729
                                      carboxylic acid 21798
                                        carboacyl group 19584
                                          univalent carboacyl group 19584
                                            carbamoyl group 19016
                                              carboxamide 19016
                                                peptide 9917
                                                  oligopeptide 1268
                                                    dipeptide 375
                                                      Z-Val-Phe-H 11
paths to the root