methyl 2-(2-methoxy-2-oxoacetamido)acetate

• ChemBase编号: 10776
• 分子式: C6H9NO5
• 平均质量: 175.13936
• 单一同位素质量: 175.04807239
• SMILES: O=C(OC)C(=O)NCC(=O)OC
• Canonical SMILES: COC(=O)CNC(=O)C(=O)OC
• InChI: InChI=1S/C6H9NO5/c1-11-4(8)3-7-5(9)6(10)12-2/h3H2,1-2H3,(H,7,9)
• InChIKey: BNJOZDZCRHCODO-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: methyl 2-(2-methoxy-2-oxoacetamido)acetate
• IUPAC传统名: methyl 2-(2-methoxy-2-oxoacetamido)acetate
• 别名: DMOG; Dimethyloxalylglycine; Dimethyloxalylglycine; N-(Methoxyoxoacetyl)-glycine methyl ester; DMOG

登记号

• CAS号: 89464-63-1
• MDL号: MFCD05865098
• PubChem SID: 160974083
• PubChem CID: 560326

理论计算性质

• Acid pKa: 11.076322
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): -0.8439144
• LogD (pH = 7.4): -0.84399444
• Log P: -0.8439134
• 摩尔折射率: 36.7803 cm^3
• 极化性: 14.78407 Å^3
• 极化表面积: 81.7 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: H2O: >30 mg/mL
• 外观: white to off-white

安全信息

• 保存注意事项: IRRITANT
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• TSCA收录: false
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 保存温度: -20°C

药理学性质

• 作用靶点: Hydroxylase

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Free Base
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C6H9NO5

详细说明

Sigma Aldrich - D3695

Biochem/physiol Actions
DMOG is a cell permeable prolyl-4-hydroxylase inhibitor, which upregulates HIF (hypoxia-inducible factor). The protein level of HIF-1α subunit is post-transcriptionally regulated by prolyl and asparaginyl hydroxylase (PAH). Suppression of PAH activity increases endogenous HIF-1α levels. DMOG is a cell permeable, competitive inhibitor of prolyl hydroxylase domain-containing proteins (PHDs and HIF-PHs). It has been discovered that the DMOG posseses neuroprotective effect on NFG deprived cell cultures through preservation of glucose metabolism. DMOG also attenuates myocardial injury in a rabbit ischemia reperfusion model. DMOG is more potent than the older inhibitor 4-Phenyl-pyridine-2,5-dicarboxylic acid (R395889; Sigma-Aldrich rare chemicals library). The IC50 is 5.18 μM.