Dimethyloxalylglycine
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Basic information
- CAS
89464-63-1- Standard SMILES
COC(=O)CNC(=O)C(=O)OC- InChIKey
BNJOZDZCRHCODO-UHFFFAOYSA-N- Molecular formula
- C6H9NO5
- Average molar mass
- 175.14 g/mol
- Monoisotopic mass
- 175.04807239
Overview
Dimethyloxalylglycine is a glycine derivative that is the diester obtained by formal condensation of the carboxy groups of N-oxalylglycine with two molecules of methanol. It has a role as an EC 1.14.11.29 (hypoxia-inducible factor-proline dioxygenase) inhibitor and a neuroprotective agent. It is a secondary carboxamide, a glycine derivative and a methyl ester. It is functionally related to a N-oxalylglycine.
Names & identifiers
- Preferred name
- Dimethyloxalylglycine
- IUPAC
- methyl 2-[(2-methoxy-2-oxoethyl)amino]-2-oxoacetate
- English name
- DMOG
- Molecular formula
- C6H9NO5
- Molecular weight
- 175.14
Names & synonyms
dimethyloxalylglycineCHEBI:102218RefChem:813279DMOG89464-63-1DIMETHYLOXALOYLGLYCINEDimethyloxallyl glycinemethyl 2-((2-methoxy-2-oxoethyl)amino)-2-oxoacetatedimethyloxaloylglycine (dmog)methyl 2-[(2-methoxy-2-oxoethyl)amino]-2-oxoacetatemethyl n-[methoxy(oxo)acetyl]glycinateMFCD05865098
Show more names
OMOGOMODMOG, >=98%DMOG USP/EP/BPDimethyloxalylglycine (Dmog)
CHEMBL92309N-(methoxyoxoacetyl)-glycine, methyl esterGlycine, N-(methoxyoxoacetyl)-, methyl esterN-(2-Methoxy-2-oxoacetyl)glycine methyl esterAS-40798methyl N-(2-methoxy-2-oxoacetyl)glycinatemethyl 2-(2-methoxy-2-oxoacetamido)acetateN-[(Methoxycarbonyl)methyl]oxamic Acid Methyl Ester; N-(methoxyoxoacetyl)glycine Methyl Ester; DMOG;
Database identifiers
- CAS
89464-63-1- PubChem CID
- 560326
- DTXSID
DTXSID80339961
Properties
Computed structural propertiesFilling in
- XLogP
- -0.3
- Topological polar surface area
- 81.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 200
Physicochemical properties
- Melting point
- 46 · 46-48°C
- Boiling point
- 179 · 179-182 °C(Press: 12 Torr)
- Density
- 1.246 · 1.246±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 2 O: · H2O: >30mg/mL
- pka
- 10.55 · 10.55±0.46(Predicted)
- form
- Solid
- color
- white to off-white
- Water Solubility
- 30 mg/ml · Soluble in water at 30mg/ml.
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions are not stable. Solutions must be made fresh and used within 1 working day.
- 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
- SMILES
- C(OC)(=O)CNC(C(OC)=O)=O
- UNSPSC Code
- 12352200 · 12352200
- NACRES
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- hs_code
- 2924.19.8000
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Applications
DescriptionThe pro-angiogenic factor HIF-1α is targeted for destruction in normoxic environments by the hydroxylation of a specific proline residue, P564, by the oxygen-sensing enzyme HIF-1α prolyl hydroxylase (HIF-PH). DMOG is a cell permeable, competitive inhibitor of HIF-PH. It acts to stabilize HIF-1α expression at normal oxygen tensions in cultured cells, at concentrations between 0.1 and 1 mM. DMOG is therefore expected to act as a pro-angiogenic compound, acting via the HIF-1α system.
UsesDMOG is a cell permeable prolyl-4-hydroxylase inhibitor which upregulates HIF activity. HIF activation stimulates angiogenesis in several different models (1nM). DMOG also inhibits FIH (factor inhibiting HIF), an asparaginyl hydroxylase, which enhances the HIF response. It is active in vivo and attenuates myocardial injury in a rabbit ischemia reperfusion model (20mg/Kg).
UsesDMOG is a cell permeable prolyl-4-hydroxylase inhibitor that regulates hypoxia-inducible factor
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: Dimethyloxalylglycine is a glycine derivative that is the diester obtained by formal condensation of the carboxy groups of N-oxalylglycine with two molecules of methanol. It has a role as a neuroprotective agent and an EC 1.14.11.29 (hypoxia-inducible factor-proline dioxygenase) inhibitor. It is a glycine derivative, a methyl ester and a secondary carboxamide. It is functionally related to a N-oxalylglycine.
Related reactions
1 records
Compound notes
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