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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 ISO calpain inhibitor III inhibits the reaction [Tetrachlorodibenzodioxin results in increased degradation of AHR protein] CTD PMID:16891617 NCBI chr 6:54,963,990...55,001,806
Ensembl chr 6:54,963,990...55,001,464
JBrowse link
G Aifm1 apoptosis inducing factor, mitochondria associated 1 multiple interactions EXP 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:135,304,063...135,343,062
Ensembl chr  X:135,304,066...135,343,087
JBrowse link
G Capn1 calpain 1 multiple interactions
decreases activity
ISO
EXP
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 chr 1:221,346,081...221,370,965
Ensembl chr 1:221,346,066...221,370,322
JBrowse link
G Capn2 calpain 2 multiple interactions EXP calpain inhibitor III inhibits the reaction [Isoflurane results in increased expression of CAPN2 protein] CTD PMID:29289695 NCBI chr13:100,878,649...100,928,811
Ensembl chr13:100,878,650...100,928,811
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions ISO calpain inhibitor III inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of CYP1A1 mRNA] CTD PMID:16891617 NCBI chr 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
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 3:13,838,304...13,842,763
Ensembl chr 3:13,838,304...13,842,762
JBrowse link
G Il1a interleukin 1 alpha affects localization ISO calpain inhibitor III affects the localization of IL1A protein CTD PMID:24024155 NCBI chr 3:121,824,712...121,836,122
Ensembl chr 3:121,825,412...121,836,086
JBrowse link
G Nefl neurofilament light multiple interactions EXP calpain inhibitor III inhibits the reaction [Zymosan results in increased degradation of NEFL protein] CTD PMID:15275793 NCBI chr15:44,799,378...44,803,251
Ensembl chr15:44,799,334...44,804,574
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 chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
JBrowse link
G Sptan1 spectrin, alpha, non-erythrocytic 1 multiple interactions ISO
EXP
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 3:8,534,437...8,599,259
Ensembl chr 3:8,534,440...8,599,260
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 chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19787
    role 19734
      biological role 19734
        inhibitor 18223
          apoptosis inhibitor 6777
            Z-Val-Phe-H 11
Path 2
Term Annotations click to browse term
  CHEBI ontology 19787
    subatomic particle 19784
      composite particle 19784
        hadron 19784
          baryon 19784
            nucleon 19784
              atomic nucleus 19784
                atom 19784
                  main group element atom 19672
                    p-block element atom 19672
                      carbon group element atom 19574
                        carbon atom 19563
                          organic molecular entity 19563
                            organic group 18495
                              organic divalent group 18488
                                organodiyl group 18488
                                  carbonyl group 18391
                                    carbonyl compound 18391
                                      carboxylic acid 18061
                                        carboacyl group 17348
                                          univalent carboacyl group 17348
                                            carbamoyl group 17134
                                              carboxamide 17134
                                                peptide 9392
                                                  oligopeptide 1196
                                                    dipeptide 372
                                                      Z-Val-Phe-H 11
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.