Compound: Leupeptin
SMILES: O=C(N[C@H](C(=O)N[C@H](C=O)CCCNC(=N)N)CC(C)C)[C@@H](NC(=O)C)CC(C)C
InChIKey: GDBQQVLCIARPGH-ULQDDVLXSA-N
Synonyms: Leupeptin, 55123-66-5, CHEBI:6426, J97339NR3V, acetyl-l-leucyl-l-leucyl-l-argininal, (2S)-2-acetamido-N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-4-methylpentanamide, N-Acetyl-L-leucyl-L-leucyl-L-argininal, DTXSID1020776, L-LEUCINAMIDE, N-ACETYL-L-LEUCYL-N-((1S)-4-((AMINOIMINOMETHYL)AMINO)-1-FORMYLBUTYL)-, L-LEUCINAMIDE, N-ACETYL-L-LEUCYL-N-(4-((AMINOIMINOMETHYL)AMINO)-1-FORMYLBUTYL)-, (S)-, L-Leucinamide, N-acetyl-L-leucyl-N-[(1S)-4-[(aminoiminomethyl)amino]-1-formylbutyl]-, (2S)-2-acetamido-N-((2S)-1-(((2S)-5-(diaminomethylideneamino)-1-oxopentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)-4-methylpentanamide, RefChem:799002, DTXCID90776, 600-443-5, 640-991-2, 686-481-3, 103476-89-7, Ac-Leu-Leu-Arg-H, 24365-47-7, Acetyl-L-leucyl-L-leucylargininal, C20H38N6O4, Leupeptin (hemisulfate), Ac-LLR-H, LEUPEPTINS [MI], BSPBio_001195, KBioGR_000535, KBioSS_000535, N-acetyl-leucylleucylargininal, Ac-L-Leu-L-Leu-L-Arg-H, SCHEMBL583830, UNII-J97339NR3V, CHEMBL191881, SCHEMBL4458973, SCHEMBL10378726, KBio2_000535, KBio2_003103, KBio2_005671, KBio3_000969, KBio3_000970, L-Leucinamide, N-acetyl-L-leucyl-N-[4-[(aminoiminomethyl)amino]-1-formylbutyl]-, N-acetyl-L-leucyl-N-[(2S)-5-carbamimidamido-1-oxopentan-2-yl]-L-leucinamide, Bio2_000428, Bio2_000908, HMS1362K17, HMS1792K17, HMS1990K17, HMS3403K17, BDBM50213272, AKOS024456431, FL29627, (S)-2-(2-Acetamido-4-methylvaleramido)-N-(1-formyl-4-guanidinobutyl)-4-methyl-valeramide, IDI1_002183, N-acetyl-L-leucyl-N-[(1S)-4-{[amino(imino)methyl]amino}-1-formylbutyl]-L-leucinamide, Valeramide, 2-(2-acetamido-4-methylvaleramido)-N-(1-formyl-4-guanidinobutyl)-4-methyl- (S)-, NCGC00163460-01, NCGC00163460-02, NCGC00163460-03, (2S)-2-acetamido-N-[(1S)-1-[[(1S)-1-formyl-4-guanidino-butyl]carbamoyl]-3-methyl-butyl]-4-methyl-pentanamide, AC-35848, DA-64931, HY-18234, CS-0007311, Q11350119, N-Acetyl-L-leucyl-L-leucyl-L-arginine, aldehyde deriv., Ac-Leu-Leu-Arg-H; N-Acetyl-L-leucyl-L-leucyl-L-arginine, aldehyde deriv, (S)-2-Acetamido-N-((S)-1-((S)-5-guanidino-1-oxopentan-2-ylamino)-4-methyl-1-oxopentan-2-yl)-4-methylpentanamide, L-Leucinamide, N-acetyl-L-leucyl-N-[(1S)-4-[(aminoiminomethyl)amino]-1-formylbutyl]-, sulfate
Theoretical properties:
molecular_formula: C20H38N6O4
molecular_weight: 426.6 g/mol
exact_mass: 426.29545371 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 14
heavy_atom_count: 30
topological_polar_surface_area: 169 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Leupeptin is 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. It has a role as a serine protease inhibitor, a cathepsin B inhibitor, an EC 3.4.21.4 (trypsin) inhibitor, a bacterial metabolite and a calpain inhibitor. It is an aldehyde and a tripeptide. It is a conjugate base of a leupeptin(1+).", "chebi": "A tripeptide composed of <em>N</em>-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.", "chembl": "LEUPEPTIN is a protein listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Leupeptin, also known as N-acetyl-L-leucyl-L-leucyl-L-argininal, is a naturally occurring protease inhibitor that can inhibit cysteine, serine and threonine peptidases.\nIt is often used during in vitro experiments when a specific enzymatic reaction is being studied. When cells are lysed for these studies, proteases, many of which are contained within lysosomes, are released. These proteases, if freely present in the lysate, would destroy any products from the reaction being studied, and make the experiment uninterpretable. For example, leupeptin could be used in a calpain extraction to keep calpain from being hydrolyzed by specific proteases. The suggested concentration is 1-10 \u03bcM (0.5-5 \u03bcg/ml).\nLeupeptin is an organic compound produced by actinomycetes, which inhibits serine, cysteine and threonine proteases.  Leupeptin inhibits serine proteinases (trypsin (Ki=3.5 nM), plasmin (Ki= 3.4 nM), porcine kallikrein), and cysteine proteinases (papain, cathepsin B (Ki = 4.1 nM), endoproteinase Lys-C). It does not inhibit \u03b1-chymotrypsin or thrombin. Leupeptin is a competitive transition state inhibitor and its inhibition may be relieved by an excess of substrate.\nLeupeptin is soluble in water (stable for 1 week at 4 \u00b0C and 1 month at \u221220 \u00b0C), ethanol, acetic acid and DMF.\nIt can be given topically for middle and inner ear infections."}