leupeptin (CHEBI:6426)

CHEBI:6426 - leupeptin

ChEBI ID	CHEBI:6426
ChEBI Name	leupeptin
Stars
Definition	A tripeptide composed of N-acetylleucyl, leucyl and argininal residues joined in sequenceby peptide linkages. It is an inhibitor of the calpains, a family of calcium-activated proteases which promote cell death.
Last Modified	24 June 2022
Downloads	Molfile

Formula	C20H38N6O4
Net Charge	0
Average Mass	426.562
Monoisotopic Mass	426.29545
SMILES	[H]C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(C)=O
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

Wikipedia

Species of Metabolite	Component	Source	Comments
Streptomyces exfoliatus (ncbitaxon:1905)	-	PubMed (9531495)	Strain: SMF13

Roles Classification

Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).

bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria.

serine protease inhibitor Any protease inhibitor that restricts the action of a serine protease.

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).

cathepsin B inhibitor A cysteine protease inhibitor which inhibits cathepsin B (EC 3.4.22.1).

calpain inhibitor An EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the action of any calpain.

ChEBI Ontology

Outgoing Relation(s)
	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)
	leupeptin (CHEBI:6426) is conjugate base of leupeptin(1+) (CHEBI:192489)
Incoming Relation(s)
Incoming Relation(s)	leupeptin(1+) (CHEBI:192489) is conjugate acid of leupeptin (CHEBI:6426)

IUPAC Name
N-acetyl-L-leucyl-N-[(2S)-5-carbamimidamido-1-oxopentan-2-yl]-L-leucinamide

Synonyms	Source
Ac-Leu-Leu-Arg-H	ChEBI
Ac-L-Leu-L-Leu-L-Arg-H	ChEBI
N-acetyl-leucylleucylargininal	ChEBI
N-acetyl-L-leucyl-L-leucyl-L-argininal	ChEBI
Ac-LLR-H	ChEBI
Ac-Leu-Leu-argininal	ChEBI

Citations