{[(2R,3R,5R)-3-hydroxy-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-2-yl]methoxy}phosphonic acid

• ChemBase编号: 168289
• 分子式: C12H14N5O6P
• 平均质量: 355.243221
• 单一同位素质量: 355.06816982
• SMILES: [C@H]1(C[C@@H](O[C@@H]1COP(=O)(O)O)n1c2ncn3c(c2nc1)ncc3)O
• Canonical SMILES: O[C@@H]1C[C@@H](O[C@@H]1COP(=O)(O)O)n1cnc2c1ncn1c2ncc1
• InChI: InChI=1S/C12H14N5O6P/c18-7-3-9(23-8(7)4-22-24(19,20)21)17-6-14-10-11-13-1-2-16(11)5-15-12(10)17/h1-2,5-9,18H,3-4H2,(H2,19,20,21)/t7-,8-,9-/m1/s1
• InChIKey: CACCSKNYAUKFAV-IWSPIJDZSA-N

名称和登记号

名称

• IUPAC标准名: {[(2R,3R,5R)-3-hydroxy-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-2-yl]methoxy}phosphonic acid
• IUPAC传统名: [(2R,3R,5R)-3-hydroxy-5-{imidazo[2,1-f]purin-3-yl}oxolan-2-yl]methoxyphosphonic acid
• 别名: 3-(2-Deoxy-5-O-phosphono-β-D-erythro-pentofuranosyl)-3H-imidazo[2,1-i]purine; 1,N6-Etheno-2'-deoxy-AMP; Etheno-2'-deoxy-β-D-adenosine 5'-Monophosphate

登记号

• CAS号: 60508-81-8
• PubChem SID: 162262421
• PubChem CID: 71316499

理论计算性质

• Acid pKa: 1.2516966
• 质子受体: 8
• 质子供体: 3
• LogD (pH = 5.5): -3.9783697
• LogD (pH = 7.4): -5.0915956
• Log P: -3.7179263
• 摩尔折射率: 78.954 cm^3
• 极化性: 31.056107 Å^3
• 极化表面积: 144.23 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

详细说明

Toronto Research Chemicals - E890385

A phosphorylated adenosine derivative used as probes of the activator site of glycogen phosphorylase. It is used in method for detecting misincorporation during DNA synthesis.

参考文献

• Vandenbunder, B. et al.: Proc, Nat. Acd. Sci. U.S.A., 73, 2696 (1976)
• Revich, G.G. et al.: Carcinogen., 7, 1569 (1976)