2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-nitro-6,9-dihydro-1H-purin-6-one

• ChemBase编号: 175242
• 分子式: C10H12N6O7
• 平均质量: 328.23828
• 单一同位素质量: 328.07674675
• SMILES: [nH]1c(nc2c(c1=O)nc(n2[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)[N+](=O)[O-])N
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1c(nc2c1nc(N)[nH]c2=O)[N+](=O)[O-]
• InChI: InChI=1S/C10H12N6O7/c11-9-13-6-3(7(20)14-9)12-10(16(21)22)15(6)8-5(19)4(18)2(1-17)23-8/h2,4-5,8,17-19H,1H2,(H3,11,13,14,20)/t2-,4-,5-,8-/m1/s1
• InChIKey: KGUOMRFOXYDMAH-UMMCILCDSA-N

名称和登记号

名称

• IUPAC标准名: 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-nitro-6,9-dihydro-1H-purin-6-one
• IUPAC传统名: 8-nitroguanosine
• 别名: 8-Nitroguanosine

登记号

• CAS号: 337536-53-5
• PubChem SID: 164231152
• PubChem CID: 16727417

理论计算性质

• Acid pKa: 10.0601015
• 质子受体: 10
• 质子供体: 5
• LogD (pH = 5.5): -2.081998
• LogD (pH = 7.4): -2.082825
• Log P: -2.081984
• 摩尔折射率: 71.4191 cm^3
• 极化性: 26.463879 Å^3
• 极化表面积: 201.04 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

详细说明

Toronto Research Chemicals - N496050

A highly reactive redox-active nucleic acid derivative that is is formed in cellular RNA as biomarker of exposure to reactive nitrogen species. Recent studies suggest that it might contribute to the pathogenesis of inflammation-associated carcinogenesis.

参考文献

• Sawa, T. et al.: Biochem. Biophys. Res. Comm., 311, 300 (2003)
• Masuda, M. et al.: Chem.-Biol. Inter., 139, 187 (2003)
• Kaneko, K. et al.: Cancer Lett., 262, 239 (2003)