(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}-9H-purin-9-yl)oxolane-3,4-diol

• ChemBase编号: 131226
• 分子式: C17H17N5O6S
• 平均质量: 419.41178
• 单一同位素质量: 419.08995429
• SMILES: c1cc(ccc1CSc1c2c(ncn1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)[N+](=O)[O-]
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2SCc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C17H17N5O6S/c23-5-11-13(24)14(25)17(28-11)21-8-20-12-15(21)18-7-19-16(12)29-6-9-1-3-10(4-2-9)22(26)27/h1-4,7-8,11,13-14,17,23-25H,5-6H2/t11-,13-,14-,17-/m1/s1
• InChIKey: DYCJFJRCWPVDHY-LSCFUAHRSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}-9H-purin-9-yl)oxolane-3,4-diol
• IUPAC传统名: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}purin-9-yl)oxolane-3,4-diol
• 别名: 6-[(4-硝基苄基)硫代]-9-β-D-呋喃核糖基嘌呤; S-(4-硝基苄基)-6-硫肌苷; NBMPR; NBTI; S-(4-Nitrobenzyl)-6-thioinosine; 6-[(4-Nitrobenzyl)thio]-9-β-D-ribofuranosylpurine

登记号

• CAS号: 38048-32-7
• EC号: 253-753-4
• MDL号: MFCD00005745
• PubChem SID: 162225504; 24277723
• PubChem CID: 65407

理论计算性质

• Acid pKa: 12.454004
• 质子受体: 9
• 质子供体: 3
• LogD (pH = 5.5): 0.8909769
• LogD (pH = 7.4): 0.9263837
• Log P: 0.92685854
• 摩尔折射率: 103.2406 cm^3
• 极化性: 39.756 Å^3
• 极化表面积: 159.34 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: 0.1 M HCl: slightly soluble; 0.1 M NaOH: slightly soluble; DMSO: soluble; H2O: insoluble
• 外观: white solid
• 熔点: 187-190 °C(lit.)

安全信息

• RTECS编号: UO9025000
• 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

药理学性质

• 相关基因信息: human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), SLC29A1(2030)

产品相关信息

• 纯度: ≥98%; 98%
• Empirical Formula (Hill Notation): C17H17N5O6S

详细说明

Sigma Aldrich - N2255

Biochem/physiol Actions
Potent adenosine uptake inhibitor
Inhibitor of equilibrative nucleoside transporters (ENTs), particularly adenosine transporters, in central nervous system1 and vascular smooth muscle.2

Sigma Aldrich - N127

Biochem/physiol Actions
Inhibitor of equilibrative nucleoside transporters (ENTs), particularly adenosine transporters, in central nervous system1 and vascular smooth muscle.2

Sigma Aldrich - 861499

Application
极强的核苷转运抑制剂。在培养中，NBMPR 可牢固但可逆地结合到与核苷转运机制相关的肿瘤细胞膜位点上，因此是一种可用于癌症研究的有用工具。
Biochem/physiol Actions
Inhibitor of equilibrative nucleoside transporters (ENTs), particularly adenosine transporters, in central nervous system1 and vascular smooth muscle.2