(2S)-2-[(2S)-2-acetamido-4-methylpentanamido]-4-methyl-N-[(2S)-1-oxohexan-2-yl]pentanamide

• ChemBase编号: 5201
• 分子式: C20H37N3O4
• 平均质量: 383.52548
• 单一同位素质量: 383.27840668
• SMILES: N([C@H](C(=O)N[C@H](C(=O)N[C@H](C=O)CCCC)CC(C)C)CC(C)C)C(=O)C
• Canonical SMILES: CCCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(C)C)CC(C)C)C=O
• InChI: InChI=1S/C20H37N3O4/c1-7-8-9-16(12-24)22-19(26)18(11-14(4)5)23-20(27)17(10-13(2)3)21-15(6)25/h12-14,16-18H,7-11H2,1-6H3,(H,21,25)(H,22,26)(H,23,27)/t16-,17-,18-/m0/s1
• InChIKey: FMYKJLXRRQTBOR-BZSNNMDCSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-[(2S)-2-acetamido-4-methylpentanamido]-4-methyl-N-[(2S)-1-oxohexan-2-yl]pentanamide
• IUPAC传统名: N-ac-leu-leu-norleucinal; (2S)-2-[(2S)-2-acetamido-4-methylpentanamido]-4-methyl-N-[(2S)-1-oxohexan-2-yl]pentanamide
• 别名: 2-ACETYLAMINO-4-METHYL-PENTANOIC ACID [1-(1-FORMYL-PENTYLCARBAMOYL)-3-METHYL-BUTYL]-AMIDE; ALLN; Ac-LLnL-CHO; MG-101; N-Acetyl-Leu-Leu-Norleu-al; N-Acetyl-L-leucyl-L-leucyl-L-norleucinal; Calpain Inhibitor I

登记号

• CAS号: 110044-82-1
• MDL号: MFCD00065505
• Beilstein号: 7656053
• PubChem SID: 160968631; 24852739; 24891066; 99444029
• PubChem CID: 443118

理论计算性质

JChem

• LogD (pH = 7.4): 1.928358
• Log P: 1.928361
• 摩尔折射率: 104.6837 cm^3
• 极化性: 41.28852 Å^3
• 极化表面积: 104.37 Å^2
• 可自由旋转的化学键: 13
• 里宾斯基五规则: true
• Acid pKa: 12.485252
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): 1.9283609

ALOGPS 2.1

• Log P: 2.22
• LOG S: -3.81
• 溶解度: 5.96e-02 g/l

分子性质

理化性质

• 溶解度: DMSO: soluble; ethanol: soluble
• 外观: white powder

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... CAPN1(823), CTSB(1508), PSMA1(5682)

产品相关信息

• 纯度: ≥97% (TLC); ≥97.0% (TLC)
• Empirical Formula (Hill Notation): C20H37N3O4

详细说明

DrugBank - DB07558

Drug information: experimental

Sigma Aldrich - A6185

Application
Calpain inhibitor I reversibly blocks the calcium-dependent neutral cysteine protease calpain I. Calpains have been implicated in various cellular processes, including cell proliferation, apoptosis, and cell differentiation.
Biochem/physiol Actions
Can initiate apoptosis in HL-60 cells1 but blocks dexamethasone-induced apoptosis in thymocytes and cycloheximide-induced apoptosis in metamyelocytes.2 Inhibits cyclin B degradation and arrests the cell cycle at G1/S and at meta-/anaphase.3 Blocks induction of nitric oxide synthase by LPS in macrophages.4

Sigma Aldrich - 21277

Other Notes
Shows marked inhibition of cathepsin L1