(1R,5S)-1-[(1S)-1-hydroxy-2-methylpropyl]-4,4-dimethyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

• ChemBase编号: 173078
• 分子式: C11H17NO4
• 平均质量: 227.25698
• 单一同位素质量: 227.11575803
• SMILES: [C@]12([C@@H](OC1=O)C(C(=O)N2)(C)C)[C@H](C(C)C)O
• Canonical SMILES: CC([C@@H]([C@]12NC(=O)C([C@@H]2OC1=O)(C)C)O)C
• InChI: InChI=1S/C11H17NO4/c1-5(2)6(13)11-7(16-9(11)15)10(3,4)8(14)12-11/h5-7,13H,1-4H3,(H,12,14)/t6-,7-,11+/m0/s1
• InChIKey: SFIBAAAUUBBTJU-OKTBNZSVSA-N

名称和登记号

名称

• IUPAC标准名: (1R,5S)-1-[(1S)-1-hydroxy-2-methylpropyl]-4,4-dimethyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• IUPAC传统名: (1R,5S)-1-[(1S)-1-hydroxy-2-methylpropyl]-4,4-dimethyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• 别名: (1R,5S)-1-[(1S)-1-Hydroxy-2-methylpropyl]-4,4-dimethyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione; (-)-7-Methylomuralide; α-Methyl Omuralide

登记号

• CAS号: 215232-00-1
• PubChem SID: 164228988
• PubChem CID: 10513481

理论计算性质

• Acid pKa: 10.4539175
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 0.6447277
• LogD (pH = 7.4): 0.6443923
• Log P: 0.644732
• 摩尔折射率: 54.55 cm^3
• 极化性: 22.218525 Å^3
• 极化表面积: 75.63 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

详细说明

Toronto Research Chemicals - M265145

Potent, selective, irreversible inhibitor of proteasome function. A cell permeable α-methyl analog of clasto-Lactacytin (C562500).

参考文献

• Saravanan, P. et al.: J. Org. Chem. 68, 2760 (2003)
• Corey, E.J., et al.: Tetrahedron Lett. 39, 7475 (2003)