(2S)-2-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid hydrochloride

• ChemBase编号: 132429
• 分子式: C16H25ClN2O4
• 平均质量: 344.8337
• 单一同位素质量: 344.15028497
• SMILES: CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](Cc1ccccc1)N)O.Cl
• Canonical SMILES: O[C@H](C(=O)N[C@H](C(=O)O)CC(C)C)[C@@H](Cc1ccccc1)N.Cl
• InChI: InChI=1S/C16H24N2O4.ClH/c1-10(2)8-13(16(21)22)18-15(20)14(19)12(17)9-11-6-4-3-5-7-11;/h3-7,10,12-14,19H,8-9,17H2,1-2H3,(H,18,20)(H,21,22);1H/t12-,13+,14+;/m1./s1
• InChIKey: XGDFITZJGKUSDK-UDYGKFQRSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid hydrochloride
• IUPAC传统名: ubenimex hydrochloride
• 别名: N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine hydrochloride; Bestatin hydrochloride

登记号

• CAS号: 65391-42-6
• MDL号: MFCD00058004
• Beilstein号: 4628066
• PubChem SID: 24278278; 162226706
• PubChem CID: 11957481

理论计算性质

• Acid pKa: 3.7260025
• 质子受体: 5
• 质子供体: 4
• LogD (pH = 5.5): -1.1024202
• LogD (pH = 7.4): -1.1396116
• Log P: -1.0995758
• 摩尔折射率: 82.0498 cm^3
• 极化性: 32.62761 Å^3
• 极化表面积: 112.65 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: H2O: soluble25 mg/mL, clear, colorless
• 熔点: 216-218 °C

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

产品相关信息

• 纯度: ≥98% (HPLC); ≥99.0% (HPLC)
• 产品质量级别: PREMIUM
• Empirical Formula (Hill Notation): C16H24N2O4 · HCl

详细说明

Sigma Aldrich - B8385

Preparation Note
Solubility testing in water at 25 mg/ml yields a clear solution. Stock solutions at 1 mM are expected to be stable at least one month stored at -20 °C.
Biochem/physiol Actions
A metalloprotease inhibitor selective for aminopeptidase. Bestatin is a competitive and specific inhibitor of leucine aminopeptidase, aminopeptidase B, and triamino peptidase. It inhibits aminopeptidase B at 60 nM (using arginine-β-naphthylamide as substrate) and leucine aminopeptidase at 20 nM (leucine-β-naphthylamide as substrate). It showed no inhibition of aminopeptidase A, trypsin, chymotrypsin, elastase, papain, pepsin, or themolysin. It offers promise as a novel analgesic because it protects endogenous opioid peptides against degradation.1

Sigma Aldrich - 08170

Other Notes
Specific inhibitor of aminopeptidase B and leucine aminopeptidase2; Immunomodifier3; other biological effects see4
Biochem/physiol Actions
A metalloprotease inhibitor selective for aminopeptidase. Bestatin is a competitive and specific inhibitor of leucine aminopeptidase, aminopeptidase B, and triamino peptidase. It inhibits aminopeptidase B at 60 nM (using arginine-β-naphthylamide as substrate) and leucine aminopeptidase at 20 nM (leucine-β-naphthylamide as substrate). It showed no inhibition of aminopeptidase A, trypsin, chymotrypsin, elastase, papain, pepsin, or themolysin. It offers promise as a novel analgesic because it protects endogenous opioid peptides against degradation.1