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

• ChemBase ID: 10776
• Molecular Formular: C6H9NO5
• Molecular Mass: 175.13936
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-(2-methoxy-2-oxoacetamido)acetate
• IUPAC Traditional name: methyl 2-(2-methoxy-2-oxoacetamido)acetate
• Synonyms: DMOG; Dimethyloxalylglycine; Dimethyloxalylglycine; N-(Methoxyoxoacetyl)-glycine methyl ester; DMOG

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 11.076322
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.8439144
• LogD (pH = 7.4): -0.84399444
• Log P: -0.8439134
• Molar Refractivity: 36.7803 cm^3
• Polarizability: 14.78407 Å^3
• Polar Surface Area: 81.7 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >30 mg/mL
• Apperance: white to off-white

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: -20°C

Pharmacology Properties

• Target: Hydroxylase

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C6H9NO5

DETAILS

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.