EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:230455 - Ac-Tyr-Val-Ala-Asp-chloromethylketone

ChEBI IDCHEBI:230455
ChEBI NameAc-Tyr-Val-Ala-Asp-chloromethylketone
Stars
DefinitionA tetrapeptide composed of L-tyrosine, L-valine, L-alanine, and L-aspartic acid joined in sequence by peptide linkages and in which the amino terminus in substituted by an acetyl group and the carboxy terminus is substituted by a chloromethyl group.
Last Modified11 April 2024
Submitterdoughowe
DownloadsMolfile
FormulaC24H33ClN4O8
Net Charge0
Average Mass541.001
Monoisotopic Mass540.19869
SMILESCC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)CCl)C(C)C
InChIInChI=1S/C24H33ClN4O8/c1-12(2)21(24(37)26-13(3)22(35)28-17(10-20(33)34)19(32)11-25)29-23(36)18(27-14(4)30)9-15-5-7-16(31)8-6-15/h5-8,12-13,17-18,21,31H,9-11H2,1-4H3,(H,26,37)(H,27,30)(H,28,35)(H,29,36)(H,33,34)/t13-,17-,18-,21-/m0/s1
InChIKeyUOUBHJRCKHLGFB-DGJUNBOTSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
EC 3.4.22.36 (caspase-1) inhibitor  Any EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the activity of caspase-1 (EC 3.4.22.36).
Applications:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
nephroprotective agent  Any protective agent that is able to prevent damage to the kidney.
ChEBI Ontology
Outgoing Relation(s)
Ac-Tyr-Val-Ala-Asp-chloromethylketone (CHEBI:230455) has functional parent N-acetyl-L-tyrosine (CHEBI:21563)
Ac-Tyr-Val-Ala-Asp-chloromethylketone (CHEBI:230455) has functional parent L-alanine (CHEBI:16977)
Ac-Tyr-Val-Ala-Asp-chloromethylketone (CHEBI:230455) has functional parent L-aspartic acid (CHEBI:17053)
Ac-Tyr-Val-Ala-Asp-chloromethylketone (CHEBI:230455) has functional parent L-valine (CHEBI:16414)
Ac-Tyr-Val-Ala-Asp-chloromethylketone (CHEBI:230455) has role EC 3.4.22.36 (caspase-1) inhibitor (CHEBI:76795)
Ac-Tyr-Val-Ala-Asp-chloromethylketone (CHEBI:230455) has role nephroprotective agent (CHEBI:76595)
Ac-Tyr-Val-Ala-Asp-chloromethylketone (CHEBI:230455) has role neuroprotective agent (CHEBI:63726)
Ac-Tyr-Val-Ala-Asp-chloromethylketone (CHEBI:230455) is a organochlorine compound (CHEBI:36683)
Ac-Tyr-Val-Ala-Asp-chloromethylketone (CHEBI:230455) is a tetrapeptide (CHEBI:48030)
IUPAC Name 
N-acetyl-L-tyrosyl-L-valyl-N-[(2S)-1-carboxy-4-chloro-3-oxobutan-2-yl]-L-alaninamide
Synonyms  Source
Ac-YVAD-cmkChEBI
Ac-L-Tyr-L-Val-L-Ala-L-Asp-chloromethylketoneChEBI
N-acetyl-tyrosyl-valyl-alanyl-aspartyl chloromethyl ketoneChEBI
N-acetyl-tyrosinyl-valinyl-alanyl-aspartyl chloromethyl ketoneChEBI
N-acetyltyrosinylvalinylalanylaspartylchloromethyl ketoneChEBI
Manual XrefsDatabases
HMDB0249697HMDB
Registry NumbersSources
CAS:178603-78-6ChEBI
Citations