4-amino-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one

• ChemBase编号: 160924
• 分子式: C8H12N4O4
• 平均质量: 228.20528
• 单一同位素质量: 228.08585488
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)n1c(=O)nc(nc1)N)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc(nc1=O)N
• InChI: InChI=1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5-,6-/m1/s1
• InChIKey: XAUDJQYHKZQPEU-HSUXUTPPSA-N

名称和登记号

名称

• IUPAC标准名: 4-amino-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one
• IUPAC传统名: 4-amino-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
• 别名: 4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one; 2-Desoxy-5-azacytidine; 2'-Deoxy-5-azacytidine; DAC; Dacogen; Decitabine; NSC 127716; β-Decitabine; 5-Aza-2'-deoxy Cytidine

登记号

• CAS号: 2353-33-5
• PubChem SID: 162255059
• PubChem CID: 42104882

理论计算性质

• Acid pKa: 13.894836
• 质子受体: 7
• 质子供体: 3
• LogD (pH = 5.5): -2.1646957
• LogD (pH = 7.4): -2.164695
• Log P: -2.1646948
• 摩尔折射率: 50.6825 cm^3
• 极化性: 19.995268 Å^3
• 极化表面积: 120.74 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: Off-White Solid
• 熔点: >200°C (dec.)

安全信息

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

详细说明

Toronto Research Chemicals - A796950

Used as cancer treatment, in particular to inhibit the growth of pancreatic endocrine tumor cell lines.

参考文献

• Deng, T., et al.: Life Sci., 84, 311 (2009)
• Horne, H., et al.: Mol. Cancer Res., 7, 199 (2009)
• Zinner, R., et al.: Mol. Cancer Ther., 8, 521 (2009)