methyl (2S,4S,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

• ChemBase编号: 162797
• 分子式: C20H24BrClN2O9
• 平均质量: 551.76956
• 单一同位素质量: 550.03537004
• SMILES: c12c(ccc(c1Cl)Br)[nH]cc2O[C@@]1(C[C@H]([C@H]([C@@H](O1)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)OC
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@@](C[C@H]([C@H]1NC(=O)C)O)(Oc1c[nH]c2c1c(Cl)c(cc2)Br)C(=O)OC)O)O
• InChI: InChI=1S/C20H24BrClN2O9/c1-8(26)24-16-11(27)5-20(19(30)31-2,33-18(16)17(29)12(28)7-25)32-13-6-23-10-4-3-9(21)15(22)14(10)13/h3-4,6,11-12,16-18,23,25,27-29H,5,7H2,1-2H3,(H,24,26)/t11-,12+,16+,17+,18+,20+/m0/s1
• InChIKey: VATTYSQGTFSYRU-PSTHAIFASA-N

名称和登记号

名称

• IUPAC标准名: methyl (2S,4S,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• IUPAC传统名: methyl (2S,4S,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• 别名: 5-Bromo-4-chloro-3-indolyl-α-D-N-acetylneuraminic Acid, Methyl Ester

登记号

• PubChem SID: 162256932
• PubChem CID: 71307250

理论计算性质

• Acid pKa: 12.056363
• 质子受体: 8
• 质子供体: 6
• LogD (pH = 5.5): 0.38766676
• LogD (pH = 7.4): 0.3876588
• Log P: 0.38766745
• 摩尔折射率: 116.3245 cm^3
• 极化性: 47.78461 Å^3
• 极化表面积: 170.57 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: Pale Yellow Solid
• 熔点: 146-148°C

详细说明

Toronto Research Chemicals - B682285

Used as a substrate for the detection of sialidase-like enzyme in screening of enzymes, studying physiological activities of gangliosides, and recombinant technologies.

参考文献

• Biorg. Med. Chem., 1, 147 (1993)