1-[(2R,3R,4S,5R)-3-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase编号: 156028
• 分子式: C9H11N5O5
• 平均质量: 269.21414
• 单一同位素质量: 269.07601848
• SMILES: c1cn(c(=O)[nH]c1=O)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)N=[N+]=[N-]
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)N=[N+]=[N-])n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C9H11N5O5/c10-13-12-6-7(17)4(3-15)19-8(6)14-2-1-5(16)11-9(14)18/h1-2,4,6-8,15,17H,3H2,(H,11,16,18)/t4-,6-,7-,8-/m1/s1
• InChIKey: MRUKYOQQKHNMFI-XVFCMESISA-N

名称和登记号

名称

• IUPAC标准名: 1-[(2R,3R,4S,5R)-3-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC传统名: 1-[(2R,3R,4S,5R)-3-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• 别名: N3-dU; 2′-Azido-2′-deoxyuridine

登记号

• CAS号: 26929-65-7
• EC号: 248-113-6
• MDL号: MFCD00043045
• Beilstein号: 4204828
• PubChem SID: 24847215; 162250166
• PubChem CID: 168629

理论计算性质

• Acid pKa: 9.703488
• 质子受体: 7
• 质子供体: 3
• LogD (pH = 5.5): -1.7089702
• LogD (pH = 7.4): -1.7110726
• Log P: -1.5948977
• 摩尔折射率: 58.8581 cm^3
• 极化性: 22.602053 Å^3
• 极化表面积: 128.53 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 149-153 °C

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98.0% (N)
• Empirical Formula (Hill Notation): C9H11N5O5

详细说明

Sigma Aldrich - 11544

Application
2′-Azido-2′-deoxyuridine (N3-dU) upon phosphorylation to 2′-azido-2′-deoxyuridine 5′-diphosphate (N3dUDP) becomes a mechanistic inhibitor of bacterial ribonucleoside diphosphate reductase (RDPR). N3-dU has recently been evaluated for its potential use as a sensitive multi-spectroscopic probe for nucleic acids