(1S,2R,8R,8aR)-octahydroindolizine-1,2,8-triol

• ChemBase编号: 129676
• 分子式: C8H15NO3
• 平均质量: 173.2096
• 单一同位素质量: 173.10519335
• SMILES: C1C[C@H]([C@@H]2[C@@H]([C@@H](CN2C1)O)O)O
• Canonical SMILES: O[C@@H]1CN2[C@@H]([C@@H]1O)[C@H](O)CCC2
• InChI: InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1
• InChIKey: FXUAIOOAOAVCGD-WCTZXXKLSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,8R,8aR)-octahydroindolizine-1,2,8-triol
• IUPAC传统名: swainsonine
• 别名: Tridolgosir; Swainsonine; 8α,β-Octahydroindolizidine-1α,2α,8β-triol; (-)-Swainsonine

登记号

• CAS号: 72741-87-8
• PubChem SID: 162223965
• PubChem CID: 51683
• CHEMBL: 371197
• Chemspider ID: 46788
• DrugBank ID: DB02034
• KEGG ID: C10173
• 美国药典/FDA物质标识码: RSY4RK37KQ
• 维基百科标题: Swainsonine

理论计算性质

• Acid pKa: 13.284674
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): -4.78174
• LogD (pH = 7.4): -3.4669168
• Log P: -1.4067957
• 摩尔折射率: 43.1178 cm^3
• 极化性: 17.444298 Å^3
• 极化表面积: 63.93 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: 10 mg/1 mL in water; DMSO; Methanol; Water
• 外观: White to Off-White Solid
• 熔点: >125°C (dec.); 143-144 °C

安全信息

• 保存条件: -20°C Freezer

详细说明

Toronto Research Chemicals - S885000

Swainsonine is a plant alkaloid derived from Swainsona canescens (a leguminous plant). It is a reversible, active-site directed inhibitor of a-mannosidase at concentrations of 5-10mM. At acid pH, swainsonine resembles an intermediate in the hydrolysis of

参考文献

• J. Biol. Chem., 258, 7578-7585 (1983)
• Methods Enzymol., 98, 135 (1983)
• EMBO Journal, 3, 551-556 (1983)
• Mol. Cell. Biol., 5, 3467-3475 (1983)
• Int. J. Cancer, 44, 685 (1983)
• Melanoma Res., 1, 43 (1983)
• Bonay, P., & Fresno, M.: Glycobiology, 9(1983)
• 423-4