prop-2-en-1-yl (2S)-2-acetamido-3-[(3S,4R)-3-hydroxy-2-[(1R)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoate

• ChemBase编号: 172158
• 分子式: C18H28N2O7S
• 平均质量: 416.48912
• 单一同位素质量: 416.16172225
• SMILES: C1(=O)[C@@H]([C@@H](C(N1)(C(=O)SC[C@H](C(=O)OCC=C)NC(=O)C)[C@@H](C(C)C)O)O)C
• Canonical SMILES: C=CCOC(=O)[C@H](NC(=O)C)CSC(=O)C1(NC(=O)[C@@H]([C@@H]1O)C)[C@@H](C(C)C)O
• InChI: InChI=1S/C18H28N2O7S/c1-6-7-27-16(25)12(19-11(5)21)8-28-17(26)18(13(22)9(2)3)14(23)10(4)15(24)20-18/h6,9-10,12-14,22-23H,1,7-8H2,2-5H3,(H,19,21)(H,20,24)/t10-,12-,13-,14+,18?/m1/s1
• InChIKey: RYUOBJYLYRDIEH-GZIDRAAUSA-N

名称和登记号

名称

• IUPAC标准名: prop-2-en-1-yl (2S)-2-acetamido-3-[(3S,4R)-3-hydroxy-2-[(1R)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoate
• IUPAC传统名: prop-2-en-1-yl (2S)-2-acetamido-3-[(3S,4R)-3-hydroxy-2-[(1R)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoate
• 别名: Lactacystin Allyl Ester; (+)-Lactacystin Allyl Ester

登记号

• PubChem SID: 164228068
• PubChem CID: 71749713

理论计算性质

• Acid pKa: 10.407465
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): -0.34597382
• LogD (pH = 7.4): -0.34634706
• Log P: -0.345969
• 摩尔折射率: 101.9645 cm^3
• 极化性: 40.668224 Å^3
• 极化表面积: 142.03 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Acetone; Dichloromethane; DMSO; Ethyl Acetate; Methanol
• 外观: White Solid
• 熔点: 127-130°C

安全信息

• 保存条件: Refrigerator

详细说明

Toronto Research Chemicals - L101030

The precursor to Lactacystin, a selective and potent inhibitor of proteasome-mediated degradation of ubiquitin-tagged proteins. A Streptomyces metabolite that acts as a highly specific inhibitor of the 20S proteasome (MCP: multicatalytic proteinase compl

参考文献

• Fenteany, G., et al.: Science, 268, 726 (1995)
• Fenteany, G., et al.: Proc. Natl. Acad. Sci. USA, 91, 3358 (1995)