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- BIRD-PRD_000216: LEUPEPTIN -

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Basic information

EntryDatabase: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000216
StatusStatus: REF ONLY
NameLEUPEPTIN
WikipediaWikipedia - Leupeptin: 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.

It 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...

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BIRD information

TypeOligopeptide / Enzyme Inhibitor
DownloadsMolecular definition / Chemical definition / Family definition
Synonyms
  • 2-(2-acetamido-4-methylvaleramido)-N-(1-formyl-4-guanidinobutyl)-4-methylvaleramide (PubChem)
  • 2-Acetylamino-4-methyl-pentanoic acid [1-(1-formyl-4-guanidino-butylcarbamoyl)-3-methyl-butyl]-amide (PubChem)
  • 2-acetamido-N-[1-[[5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-4-methylpentanamide (PubChem)
  • Ac-LLR-CHO (PubChem)
  • Acetyl-L-leucyl-L-leucylargininal (SciFinder)
  • L-leucinamide, N-acetyl-L-leucyl-N-(4-((aminoiminomethyl)amino)-1-formylbutyl)- (PubChem)
  • Leupeptin Ac-LL (SciFinder)
  • Leupeptin hemisulfate (SciFinder)
  • Leupeptin, Hemisulfate (PubChem)
  • N-acetyl(N-propionyl)-L-leucyl-L-leucyl-D L-argininal (PDB)
  • N-acetyl-L-leucyl-L-leucyl-L-argininal (PubChem)
  • N-acetyl-L-leucyl-N-[(1R)-4-{[amino(imino)methyl]amino}-1-formylbutyl]-L-leucinamide (PubChem)
  • NK-381 (PubChem)
  • Valeramide, 2-(2-acetamido-4-methylvaleramido)-N-(1-formyl-4-guanidinobutyl)-4-methyl- (8CI) (SciFinder)
  • acetyl-L-leucyl-L-leucylargininal (PubChem)
  • leupeptin (PubChem)
  • valeramide, 2-(2-acetamido-4-methylvaleramido)-N-(1-formyl-4-guanidinobutyl)-4-methyl- (PubChem)
Annotation
  • Function: Leupeptin is a competitive inhibitor of serine and cysteine proteases reversibly. Leupeptin inhibits serine proteinases, trypsin, plasmin, porcine kallikrein, and cysteine proteinases, papain, cathepsin B, endoproteinase Lys-C. It does not inhibit chymotrypsin or thrombin. / Info source: Wikipedia
  • Function: A reversible inhibitor of trypsin-like proteases and cysteine proteases. Also known to inhibit activation-induced programmed cell death and to restore defective immune responses of HIV+ donors. / Info source: PubChem
  • Function: Class of modified protease inhibitors poroduced by various species of Actinomycetes. / Info source: Merck
  • Function: The discovery of leupeptin in the late 1960s drew attention to the potential of aldehydes as peptidase inhibitors.Many aldehydes are now known as inhibitors of serine, cysteine or threonine peptidases. They form hemiacetal orthiohemiacetal conjugates with the essential hydroxyl or thiol group of the enzyme that are transition state analogues.The compounds exist predominantly in their hydrated forms in aqueous solution, but only the aldehyde is an effectiveinhibitor. Aldehydes can also act as inhibitors of metallopeptidases. Leupeptin is a slow, tight-binding, transitionstate analogue inhibitor of cathepsin B. Leupeptin inhibits a wide range of serine (families S1, S8), cysteine(families C1, C11) and threonine (family T1) peptidases. Apart from numerous peptidases in families S1 and C1,leupeptin is a potent inhibitor of clostripain C11.001 and PACE4 S08.075 and the trypsin-like activity of theproteasome T01.011 / Info source: MEROPS
  • Function: Inhibitor of Cysteine Protease Falcipain-3,-EC: 3.4.22. / Info source: PubMed: 19128015
  • Function: Inhibitor of Kallikrein-5,-EC: 3.4.21. / Info source: PubMed: 17881000
  • Function: Inhibitor of Calpain-9;EC: 3.4.22.52 / Info source: DOI:10.2210/pdb2p0r/pdb
  • Function: Inhibitor of Cysteine Proteinase EP-B 2,-EC: 3.4.22. / Info source: PubMed: 16793521
  • Function: Inhibitor of alpha I Tryptase,EC: 3.4.21.59 / Info source: PubMed: 16414069
  • Function: Inhibitor of Calpain 1,EC: 3.4.22.52 / Info source: PubMed: 11893336
  • Function: Inhibitor of Trypsin,EC: 3.4.21.4 / Info source: PubMed: 8845765
  • Function: inhibitor of papain, EC: 3.4.22.2EC: inhibitor of papain, EC: 3.4.22.2 / Info source: PubMed: 8416808
Source
  • Actinomycetes Streptomyces roseus MA 839-A1 (bacteria), 220065: Novel Antibiotics DataBase
  • Actinomycetes Streptomyces roseus MB262-M1, 220065: Novel Antibiotics DataBase
External info
FamilyLEUPEPTIN

LEUPEPTIN

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Chemical information

Composition
Formula: C20H41N6O5 / Formula weight: 445.577
OthersType: peptide-like
History
External linksUniChem / ChemSpider / Wikipedia search / Google search

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Structure visualization

Structure viewerMolecule:
MolmilJmol/JSmol

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Details

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SMILES

ACDLabs 12.01O=C(NC(CCCNC(=[NH2+])/N)C(O)O)C(NC(=O)C(NC(=O)C)CC(C)C)CC(C)C
CACTVS 3.370CC(C)C[CH](NC(C)=O)C(=O)N[CH](CC(C)C)C(=O)N[CH](CCCNC(N)=[NH2+])C(O)O
OpenEye OEToolkits 1.7.6CC(C)CC(C(=O)NC(CC(C)C)C(=O)NC(CCCNC(=[NH2+])N)C(O)O)NC(=O)C

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SMILES CANONICAL

CACTVS 3.370CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=[NH2+])C(O)O
OpenEye OEToolkits 1.7.6CC(C)C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=[NH2+])N)C(O)O)NC(=O)C

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InChI

InChI 1.03InChI=1S/C20H40N6O5/c1-11(2)9-15(24-13(5)27)17(28)26-16(10-12(3)4)18(29)25-14(19(30)31)7-6-8-23-20(21)22/h11-12,14-16,19,30-31H,6-10H2,1-5H3,(H,24,27)(H,25,29)(H,26,28)(H4,21,22,23)/p+1

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InChIKey

InChI 1.03RBEQQMKHJLRJKG-UHFFFAOYSA-O

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SYSTEMATIC NAME

ACDLabs 12.01N-acetyl-L-leucyl-N-[(2S)-5-{[amino(iminio)methyl]amino}-1,1-dihydroxypentan-2-yl]-L-leucinamide
OpenEye OEToolkits 1.7.6[[[(4S)-4-[[(2S)-2-[[(2S)-2-acetamido-4-methyl-pentanoyl]amino]-4-methyl-pentanoyl]amino]-5,5-bis(oxidanyl)pentyl]amino]-azanyl-methylidene]azanium

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