CHEBI:6426 - leupeptin

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ChEBI Name leupeptin
ChEBI ID CHEBI:6426
Definition A tripeptide composed of N-acetylleucyl, leucyl and argininal residues joined in sequence.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H38N6O4
Net Charge 0
Average Mass 426.554
Monoisotopic Mass 426.29545
InChI InChI=1S/C20H38N6O4/c1-12(2)9-16(24-14(5)28)19(30)26-17(10-13(3)4)18(29)25-15(11-27)7-6-8-23-20(21)22/h11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23)/t15-,16-,17-/m0/s1
InChIKey GDBQQVLCIARPGH-ULQDDVLXSA-N
SMILES C([C@@H](NC([C@@H](NC([C@@H](NC(C)=O)CC(C)C)=O)CC(C)C)=O)CCCNC(=N)N)(=O)[H]
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): serine protease inhibitor
Any protease inhibitor that restricts the action of a serine protease.
calpain inhibitor
An EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the action of any calpain.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
cathepsin B inhibitor
A cysteine protease inhibitor which inhibits cathepsin B (EC 3.4.22.1).
EC 3.4.21.4 (trypsin) inhibitor
An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of trypsin (EC 3.4.21.4).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing leupeptin (CHEBI:6426) has role bacterial metabolite (CHEBI:76969)
leupeptin (CHEBI:6426) has role calpain inhibitor (CHEBI:82824)
leupeptin (CHEBI:6426) has role cathepsin B inhibitor (CHEBI:64932)
leupeptin (CHEBI:6426) has role EC 3.4.21.4 (trypsin) inhibitor (CHEBI:76940)
leupeptin (CHEBI:6426) has role serine protease inhibitor (CHEBI:64926)
leupeptin (CHEBI:6426) is a aldehyde (CHEBI:17478)
leupeptin (CHEBI:6426) is a tripeptide (CHEBI:47923)
IUPAC Name
N-acetyl-L-leucyl-N-[(2S)-5-carbamimidamido-1-oxopentan-2-yl]-L-leucinamide
Synonyms Sources
Ac-L-Leu-L-Leu-L-Arg-H ChEBI
Ac-Leu-Leu-Arg-H ChEBI
Ac-LLR-H ChEBI
N-acetyl-L-leucyl-L-leucyl-L-argininal ChEBI
N-acetyl-leucylleucylargininal ChEBI
Manual Xrefs Databases
C01591 KEGG COMPOUND
Leupeptin Wikipedia
LEUPEPTIN MetaCyc
View more database links
Registry Numbers Types Sources
2402463 Reaxys Registry Number Reaxys
24140639 Reaxys Registry Number Reaxys
55123-66-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
24393046 PubMed citation Europe PMC
26365578 PubMed citation Europe PMC
26399337 PubMed citation Europe PMC
Last Modified
03 December 2015