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

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ChEBI Name Ac-Tyr-Val-Ala-Asp-chloromethylketone
ChEBI ID CHEBI:230455
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Doug Howe
Supplier Information
Download Molfile XML SDF
Formula C24H33ClN4O8
Net Charge 0
Average Mass 541.000
Monoisotopic Mass 540.19869
InChI InChI=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
InChIKey UOUBHJRCKHLGFB-DGJUNBOTSA-N
SMILES CC(C)[C@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(C)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)CCl
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 3.4.22.36 (caspase-1) inhibitor
Any EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the activity of caspase-1 (EC 3.4.22.36).
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
Ac-L-Tyr-L-Val-L-Ala-L-Asp-chloromethylketone ChEBI
Ac-YVAD-cmk ChEBI
N-acetyl-tyrosinyl-valinyl-alanyl-aspartyl chloromethyl ketone ChEBI
N-acetyl-tyrosyl-valyl-alanyl-aspartyl chloromethyl ketone ChEBI
N-acetyltyrosinylvalinylalanylaspartylchloromethyl ketone ChEBI
Manual Xref Database
HMDB0249697 HMDB
View more database links
Registry Number Type Source
178603-78-6 CAS Registry Number ChEBI
Citations Waiting for Citations Types Sources
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Last Modified
11 April 2024