BIRD-PRD_000216: LEUPEPTIN

基本情報

• 登録情報: データベース: 生物学的重要分子辞書 (BIRD) / ID: PRD_000216
• 状態: 状態: REF ONLY
• 名称: LEUPEPTIN

BIRD information

• タイプ: オリゴペプチド / 酵素阻害剤
• ダウンロード: Molecular definition / Chemical definition / Family definition

別称

• 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

• 分子機能: 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. / 情報源: Wikipedia
• 分子機能: 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. / 情報源: PubChem
• 分子機能: Class of modified protease inhibitors poroduced by various species of Actinomycetes. / 情報源: Merck
• 分子機能: 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 / 情報源: MEROPS
• 分子機能: Inhibitor of Cysteine Protease Falcipain-3,-EC: 3.4.22. / 情報源: PubMed: 19128015
• 分子機能: Inhibitor of Kallikrein-5,-EC: 3.4.21. / 情報源: PubMed: 17881000
• 分子機能: Inhibitor of Calpain-9;EC: 3.4.22.52 / 情報源: DOI:10.2210/pdb2p0r/pdb
• 分子機能: Inhibitor of Cysteine Proteinase EP-B 2,-EC: 3.4.22. / 情報源: PubMed: 16793521
• 分子機能: Inhibitor of alpha I Tryptase,EC: 3.4.21.59 / 情報源: PubMed: 16414069
• 分子機能: Inhibitor of Calpain 1,EC: 3.4.22.52 / 情報源: PubMed: 11893336
• 分子機能: Inhibitor of Trypsin,EC: 3.4.21.4 / 情報源: PubMed: 8845765
• 分子機能: inhibitor of papain, EC: 3.4.22.2EC: inhibitor of papain, EC: 3.4.22.2 / 情報源: PubMed: 8416808

由来

• Actinomycetes Streptomyces roseus MA 839-A1 (バクテリア), 220065: Novel Antibiotics DataBase
• Actinomycetes Streptomyces roseus MB262-M1, 220065: Novel Antibiotics DataBase

External info

• BindingDB: 12041
• Calbiochem: 108975
• ChemBank: 907367
• ChemDB: 3967241
• ChemIDplus: 024365477
• LeadScope: LS-87930
• MEROPS: J00027
• Merck: 14:5456
• MESH: C032854
• ChemSpider: 2298508
• ChemSpider: 3773
• ChEBI: 109342
• ChEBI: 468978
• PubChem: 3033938
• PubChem: 3910
• PubChem: 439527
• CAS: 103476-89-7
• CAS: 24365-47-7
• [KEGG_Compound_ID] KEGG: C01591
• Wikipedia: Leupeptin
• Labome.com: leupeptin
• berkeley.edu: LEUPEPTIN
• Merck
• Nature

Family

LEUPEPTIN

LEUPEPTIN

Chemical information

組成

組成式: C₂₀H₄₁N₆O₅ / 化学式量: 445.577

• その他: タイプ: peptide-like

履歴

• 外部リンク: UniChem / ChemSpider / Wikipedia search / Google search

詳細

SMILES

• ACDLabs 12.01: O=C(NC(CCCNC(=[NH2+])/N)C(O)O)C(NC(=O)C(NC(=O)C)CC(C)C)CC(C)C
• CACTVS 3.370: CC(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 1.7.6: CC(C)CC(C(=O)NC(CC(C)C)C(=O)NC(CCCNC(=[NH2+])N)C(O)O)NC(=O)C

SMILES CANONICAL

• CACTVS 3.370: CC(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 1.7.6: CC(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

InChI

• InChI 1.03: InChI=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

InChIKey

• InChI 1.03: RBEQQMKHJLRJKG-UHFFFAOYSA-O

SYSTEMATIC NAME

• ACDLabs 12.01: N-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

PDBエントリ

全17件を表示しています

1jrs

1jrt

1pop

1tl9

2agi

2f9n

2f9p

2fo5

2nqa

2p0r

2psx

2psy

3bpm

5ms4

6bkj

7mrr

7nev