N-[1,3-bis({[(2R,3S,4R,5S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy})propan-2-yl]-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamide

• ChemBase编号: 161086
• 分子式: C24H32F3N3O13
• 平均质量: 627.5183896
• 单一同位素质量: 627.18872276
• SMILES: c1cc(ccc1C(=O)NC(CO[C@H]1[C@@H]([C@@H](C(O[C@H]1CO)O)O)O)CO[C@@H]1[C@H](OC([C@H]([C@@H]1O)O)O)CO)C1(N=N1)C(F)(F)F
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1OCC(NC(=O)c1ccc(cc1)C1(N=N1)C(F)(F)F)CO[C@@H]1[C@@H](CO)OC([C@H]([C@@H]1O)O)O)O)O
• InChI: InChI=1S/C24H32F3N3O13/c25-24(26,27)23(29-30-23)10-3-1-9(2-4-10)20(37)28-11(7-40-18-12(5-31)42-21(38)16(35)14(18)33)8-41-19-13(6-32)43-22(39)17(36)15(19)34/h1-4,11-19,21-22,31-36,38-39H,5-8H2,(H,28,37)/t11?,12-,13-,14-,15-,16+,17+,18-,19-,21?,22?/m1/s1
• InChIKey: NPJHSWNPVIJJGQ-YPYGJDMNSA-N

名称和登记号

名称

• IUPAC标准名: N-[1,3-bis({[(2R,3S,4R,5S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy})propan-2-yl]-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamide
• IUPAC传统名: N-[1,3-bis({[(2R,3S,4R,5S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy})propan-2-yl]-4-[3-(trifluoromethyl)diazirin-3-yl]benzamide
• 别名: 4,4'-O-[2-[[4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzoyl]amino]-1,3-propanediyl]bis-D-mannose; ATB-BMPA; 2-N-[4-(1-Azitrifluoroethyl)benzoyl]-1,3-bis-(D-mannos -4-yloxy)-2-propylamine

登记号

• CAS号: 129461-18-3
• PubChem SID: 162255221
• PubChem CID: 71313608

理论计算性质

• Acid pKa: 11.004429
• 质子受体: 15
• 质子供体: 9
• LogD (pH = 5.5): -2.5241203
• LogD (pH = 7.4): -2.524227
• Log P: -2.524119
• 摩尔折射率: 130.7888 cm^3
• 极化性: 51.819553 Å^3
• 极化表面积: 252.58 Å^2
• 可自由旋转的化学键: 12
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Soluble in Physiological Buffers; Water
• 外观: Off-White Solid
• 熔点: 105-107°C

安全信息

• 保存条件: -20°C Freezer, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - A927500

Used as an exofacial probe for the human erythrocyte glucose transport system. The compound is impermeable and photolabeling can be confined to the discrete plasma membrane pool of glucose transporters.

参考文献

• Holman, G.D., et al.: J. Biol. Chem., 265, 30, 18172 (1990)
• Holman, G.D., et al.: Biochem. J., 269, 615 (1990)