{[2-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)ethoxy]methyl}phosphonic acid hydrate

• ChemBase编号: 154682
• 分子式: C8H14N5O6P
• 平均质量: 307.200421
• 单一同位素质量: 307.06816982
• SMILES: c1nc2c(=O)[nH]c(nc2n1CCOCP(=O)(O)O)N.O
• Canonical SMILES: Nc1[nH]c(=O)c2c(n1)n(CCOCP(=O)(O)O)cn2.O
• InChI: InChI=1S/C8H12N5O5P.H2O/c9-8-11-6-5(7(14)12-8)10-3-13(6)1-2-18-4-19(15,16)17;/h3H,1-2,4H2,(H2,15,16,17)(H3,9,11,12,14);1H2
• InChIKey: BDVQXHFCXJXVND-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: {[2-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)ethoxy]methyl}phosphonic acid hydrate
• IUPAC传统名: [2-(2-amino-6-oxo-1H-purin-9-yl)ethoxy]methylphosphonic acid hydrate
• 别名: 9-[2-(Phosphonomethoxy)ethyl]guanine hydrate; PMEG hydrate

登记号

• MDL号: MFCD19443863
• PubChem SID: 162248820
• PubChem CID: 71311936

理论计算性质

• Acid pKa: 1.1517628
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): -4.6113367
• LogD (pH = 7.4): -4.770491
• Log P: -2.3463173
• 摩尔折射率: 64.5417 cm^3
• 极化性: 23.718493 Å^3
• 极化表面积: 152.06 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: ≥5 mg/mL
• 外观: white to off-white powder

安全信息

• 保存条件: desiccated
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 危险公开号: 25
• 安全公开号: 45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300
• GHS警示性声明: P264-P301 + P310
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C8H12N5O5P · xH2O

详细说明

Sigma Aldrich - M2199

Biochem/physiol Actions
The acyclic nucleotide 9-(2-phosphonylmethoxyethyl)guanine (PMEG) forms an active phosphorylated metabolite, PMEG diphosphate (PMEGpp), in cells and causes cytotoxicity in dividing cells due to potent inhibition of the nuclear DNA polymerases resulting in inhibition of DNA synthesis and/or DNA repair.