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Dmog

CAS No.:
89464-63-1
Catalog Number:
AG0034RM
Molecular Formula:
C6H9NO5
Molecular Weight:
175.1394
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
250mg
96%
In Stock USA
United States
$200
- +
1g
96%
In Stock USA
United States
$594
- +
Product Description
Catalog Number:
AG0034RM
Chemical Name:
Dmog
CAS Number:
89464-63-1
Molecular Formula:
C6H9NO5
Molecular Weight:
175.1394
MDL Number:
MFCD05865098
IUPAC Name:
methyl 2-[(2-methoxy-2-oxoethyl)amino]-2-oxoacetate
InChI:
InChI=1S/C6H9NO5/c1-11-4(8)3-7-5(9)6(10)12-2/h3H2,1-2H3,(H,7,9)
InChI Key:
BNJOZDZCRHCODO-UHFFFAOYSA-N
SMILES:
COC(=O)CNC(=O)C(=O)OC
Properties
Complexity:
200  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
175.048g/mol
Formal Charge:
0
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
175.14g/mol
Monoisotopic Mass:
175.048g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
81.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.3  
Literature
Title Journal
The stabilization of hypoxia inducible factor modulates differentiation status and inhibits the proliferation of mouse embryonic stem cells. Chemico-biological interactions 20160125
Featured Article: Hypoxia-inducible factor-1α dependent nuclear entry of factor inhibiting HIF-1. Experimental biology and medicine (Maywood, N.J.) 20151101
Targeting the hypoxia-sensing pathway in clinical hematology. Stem cells translational medicine 20140201
Cobalt stimulates HIF-1-dependent but inhibits HIF-2-dependent gene expression in liver cancer cells. The international journal of biochemistry & cell biology 20131101
Selective stabilization of HIF-1α in renal tubular cells by 2-oxoglutarate analogues. The American journal of pathology 20121101
Prolyl hydroxylase inhibitors increase the production of vascular endothelial growth factor in dental pulp-derived cells. Journal of endodontics 20121101
α-Ketoglutarate-related inhibitors of HIF prolyl hydroxylases are substrates of renal organic anion transporters 1 (OAT1) and 4 (OAT4). Pflugers Archiv : European journal of physiology 20121001
Activation of the prolyl-hydroxylase oxygen-sensing signal cascade leads to AMPK activation in cardiomyocytes. Journal of cellular and molecular medicine 20120901
Increased activation of the hypoxia-inducible factor pathway in varicose veins. Journal of vascular surgery 20120501
Mechanistic studies on the application of DNA aptamers as inhibitors of 2-oxoglutarate-dependent oxygenases. Journal of medicinal chemistry 20120412
Prolyl hydroxylase inhibitors increase the production of vascular endothelial growth factor by periodontal fibroblasts. Journal of periodontal research 20120401
HIF-1α induction suppresses excessive lipid accumulation in alcoholic fatty liver in mice. Journal of hepatology 20120201
Inhibition of prolyl hydroxylases by dimethyloxaloylglycine after stroke reduces ischemic brain injury and requires hypoxia inducible factor-1α. Neurobiology of disease 20120201
Hypoxia and hypoxia mimetics inhibit TNF-dependent VCAM1 induction in the 5A32 endothelial cell line via a hypoxia inducible factor dependent mechanism. Journal of dermatological science 20120201
Systemic preconditioning by a prolyl hydroxylase inhibitor promotes prevention of skin flap necrosis via HIF-1-induced bone marrow-derived cells. PloS one 20120101
Hypoxia-inducible factor activation protects the kidney from gentamicin-induced acute injury. PloS one 20120101
Inverse correlation between metallothioneins and hypoxia-inducible factor 1 alpha in colonocytes and experimental colitis. Biochemical and biophysical research communications 20111216
Activation of hypoxia-inducible factor-1 ameliorates postischemic renal injury via inducible nitric oxide synthase. Molecular and cellular biochemistry 20111201
Dimethyloxalyglycine stimulates the early stages of gastrointestinal repair processes through VEGF-dependent mechanisms. Laboratory investigation; a journal of technical methods and pathology 20111201
Activation of hypoxia-inducible factor-1 protects airway epithelium against oxidant-induced barrier dysfunction. American journal of physiology. Lung cellular and molecular physiology 20111201
Hypoxia induced expression of histone lysine demethylases: implications in oxygen-dependent retinal neovascular diseases. Biochemical and biophysical research communications 20111118
Hypoxia-inducible factor regulates expression of surfactant protein in alveolar type II cells in vitro. American journal of respiratory cell and molecular biology 20111101
Curcumin provides potential protection against the activation of hypoxia and prolyl 4-hydroxylase inhibitors on prostate-specific antigen expression in human prostate carcinoma cells. Molecular nutrition & food research 20111101
Longitudinal quantification of inflammation in the murine dextran sodium sulfate-induced colitis model using μPET/CT. Inflammatory bowel diseases 20111001
Inhibition of prolyl hydroxylase domain-containing protein downregulates vascular angiotensin II type 1 receptor. Hypertension (Dallas, Tex. : 1979) 20110901
The hydroxylase inhibitor dimethyloxallyl glycine attenuates endotoxic shock via alternative activation of macrophages and IL-10 production by B1 cells. Shock (Augusta, Ga.) 20110901
Dimethyloxalylglycine stabilizes HIF-1α in cultured human endothelial cells and increases random-pattern skin flap survival in vivo. Plastic and reconstructive surgery 20110801
Systemic pretreatment with dimethyloxalylglycine increases myocardial HIF-1α and VEGF production and improves functional recovery after acute ischemia/reperfusion. Surgery 20110801
Apigenin down-regulates the hypoxia response genes: HIF-1α, GLUT-1, and VEGF in human pancreatic cancer cells. The Journal of surgical research 20110515
Metabolic reprogramming by HIF-1 promotes the survival of bone marrow-derived angiogenic cells in ischemic tissue. Blood 20110505
[Effects of dimethyloxalyl glycine on hypoxic-ischemic brain damage in newborn rats]. Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition 20110501
Hypoxia-inducible factor-1α-dependent protection from intestinal ischemia/reperfusion injury involves ecto-5'-nucleotidase (CD73) and the A2B adenosine receptor. Journal of immunology (Baltimore, Md. : 1950) 20110401
Factor inhibiting HIF (FIH-1) promotes renal cancer cell survival by protecting cells from HIF-1α-mediated apoptosis. British journal of cancer 20110329
HIF1alpha synergizes with glucocorticoids to promote BFU-E progenitor self-renewal. Blood 20110324
Structural basis for human PHF2 Jumonji domain interaction with metal ions. Journal of molecular biology 20110211
Hydroxylase inhibition attenuates colonic epithelial secretory function and ameliorates experimental diarrhea. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20110201
Neuroprotection by dimethyloxalylglycine following permanent and transient focal cerebral ischemia in rats. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20110101
Rhapontigenin inhibited hypoxia inducible factor 1 alpha accumulation and angiogenesis in hypoxic PC-3 prostate cancer cells. Biological & pharmaceutical bulletin 20110101
Activation of Hif1α by the prolylhydroxylase inhibitor dimethyoxalyglycine decreases radiosensitivity. PloS one 20110101
von Hippel-Lindau β-domain-luciferase fusion protein as a bioluminescent hydroxyproline sensor for a hypoxia-inducible factor prolyl hydroxylase assay. Analytical biochemistry 20101215
Renal protection in chronic kidney disease: hypoxia-inducible factor activation vs. angiotensin II blockade. American journal of physiology. Renal physiology 20101201
Hydroxylase inhibition abrogates TNF-alpha-induced intestinal epithelial damage by hypoxia-inducible factor-1-dependent repression of FADD. Journal of immunology (Baltimore, Md. : 1950) 20101115
Hypoxia and preeclampsia: increased expression of urocortin 2 and urocortin 3. Reproductive sciences (Thousand Oaks, Calif.) 20100901
Force field design and molecular dynamics simulations of factor-inhibiting HIF-1 and its complex with known inhibitors: implications for rational inhibitor design. Journal of molecular graphics & modelling 20100901
Design, synthesis, enzyme-inhibitory activity, and effect on human cancer cells of a novel series of jumonji domain-containing protein 2 histone demethylase inhibitors. Journal of medicinal chemistry 20100812
Acute hypoxia induces HIF-independent monocyte adhesion to endothelial cells through increased intercellular adhesion molecule-1 expression: the role of hypoxic inhibition of prolyl hydroxylase activity for the induction of NF-kappa B. Journal of immunology (Baltimore, Md. : 1950) 20100801
Hydroxylase inhibition reduces synaptic transmission and protects against a glutamate-induced ischemia in the CA1 region of the rat hippocampus. Neuroscience 20100602
Regulation of the matricellular proteins CYR61 (CCN1) and NOV (CCN3) by hypoxia-inducible factor-1{alpha} and transforming-growth factor-{beta}3 in the human trophoblast. Endocrinology 20100601
Prolyl hydroxylase EGLN3 regulates skeletal myoblast differentiation through an NF-kappaB-dependent pathway. The Journal of biological chemistry 20100319
Characterization of connective tissue growth factor expression in primary cultures of human tubular epithelial cells: modulation by hypoxia. American journal of physiology. Renal physiology 20100301
FoxO proteins mediate hypoxic induction of connective tissue growth factor in endothelial cells. The Journal of biological chemistry 20100212
Attenuation of myocardial injury by postconditioning: role of hypoxia inducible factor-1alpha. Basic research in cardiology 20100101
Activation of hypoxia-inducible factor attenuates renal injury in rat remnant kidney. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20100101
Increased chemoresistance induced by inhibition of HIF-prolyl-hydroxylase domain enzymes. Cancer science 20100101
Inhibition of prolyl hydroxylase domain-containing protein suppressed lipopolysaccharide-induced TNF-alpha expression. Arteriosclerosis, thrombosis, and vascular biology 20091201
Combined analysis of hypoxia-inducible factor 1 alpha and metallothionein indicates an aggressive subtype of colorectal carcinoma. International journal of colorectal disease 20091101
Hypoxia interferes with connective tissue growth factor (CTGF) gene expression in human proximal tubular cell lines. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20091101
Prolyl hydroxylase inhibitors increase neoangiogenesis and callus formation following femur fracture in mice. Journal of orthopaedic research : official publication of the Orthopaedic Research Society 20091001
Interferon-gamma induces prolyl hydroxylase (PHD)3 through a STAT1-dependent mechanism in human endothelial cells. Arteriosclerosis, thrombosis, and vascular biology 20090901
Adenosine A2A receptor is a unique angiogenic target of HIF-2alpha in pulmonary endothelial cells. Proceedings of the National Academy of Sciences of the United States of America 20090630
Synthesis and activity of N-oxalylglycine and its derivatives as Jumonji C-domain-containing histone lysine demethylase inhibitors. Bioorganic & medicinal chemistry letters 20090515
Prolyl hydroxylase inhibitors depend on extracellular glucose and hypoxia-inducible factor (HIF)-2alpha to inhibit cell death caused by nerve growth factor (NGF) deprivation: evidence that HIF-2alpha has a role in NGF-promoted survival of sympathetic neurons. Molecular pharmacology 20090501
Prolyl hydroxylase inhibitor dimethyloxalylglycine enhances mesenchymal stem cell survival. Journal of cellular biochemistry 20090401
Proteomics-based identification of novel factor inhibiting hypoxia-inducible factor (FIH) substrates indicates widespread asparaginyl hydroxylation of ankyrin repeat domain-containing proteins. Molecular & cellular proteomics : MCP 20090301
Inhibition of oxygen sensors as a therapeutic strategy for ischaemic and inflammatory disease. Nature reviews. Drug discovery 20090201
HIF-1 attenuates Ref-1 expression in endothelial cells: reversal by siRNA and inhibition of geranylgeranylation. Vascular pharmacology 20090101
Prolyl hydroxylase inhibition attenuates post-ischemic cardiac injury via induction of endoplasmic reticulum stress genes. Vascular pharmacology 20090101
Regulation of Jumonji-domain-containing histone demethylases by hypoxia-inducible factor (HIF)-1alpha. The Biochemical journal 20081215
A novel mode of action of YC-1 in HIF inhibition: stimulation of FIH-dependent p300 dissociation from HIF-1{alpha}. Molecular cancer therapeutics 20081201
HIF-1alpha inhibition ameliorates neonatal brain injury in a rat pup hypoxic-ischemic model. Neurobiology of disease 20080901
Hypoxia-inducible factor-1 is central to cardioprotection: a new paradigm for ischemic preconditioning. Circulation 20080708
O(2)-sensing signal cascade: clamping of O(2) respiration, reduced ATP utilization, and inducible fumarate respiration. American journal of physiology. Cell physiology 20080701
Induction of carbonic anhydrase IX by hypoxia and chemical disruption of oxygen sensing in rat fibroblasts and cardiomyocytes. Pflugers Archiv : European journal of physiology 20080501
DHEA decreases HIF-1alpha accumulation under hypoxia in human pulmonary artery cells: potential role in the treatment of pulmonary arterial hypertension. The Journal of steroid biochemistry and molecular biology 20080301
The hydroxylase inhibitor dimethyloxalylglycine is protective in a murine model of colitis. Gastroenterology 20080101
Role of hypoxia-inducible factor 1 alpha in the integrity of articular cartilage in murine knee joints. Arthritis research & therapy 20080101
Prolyl hydroxylase inhibitors delay neuronal cell death caused by trophic factor deprivation. Journal of neurochemistry 20071201
HIF-1 regulates hypoxia- and insulin-induced expression of apelin in adipocytes. American journal of physiology. Endocrinology and metabolism 20071201
Hypoxia-inducible factor 1alpha is involved in the prostaglandin metabolism of osteoarthritic cartilage through up-regulation of microsomal prostaglandin E synthase 1 in articular chondrocytes. Arthritis and rheumatism 20071201
Hypoxia stimulates degradation of 3-hydroxy-3-methylglutaryl-coenzyme A reductase through accumulation of lanosterol and hypoxia-inducible factor-mediated induction of insigs. The Journal of biological chemistry 20070914
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Prolyl hydroxylase inhibitor treatment confers whole-animal hypoxia tolerance. Acta physiologica (Oxford, England) 20070601
Hypoxia inducible factor-1 modulates hemin-induced IL-8 secretion in microvascular endothelium. Microvascular research 20070501
Toxic effects of cobalt in primary cultures of mouse astrocytes. Similarities with hypoxia and role of HIF-1alpha. Biochemical pharmacology 20070301
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Activation of hypoxia-induced transcription in normoxia. Experimental cell research 20050515
Nitric oxide reverses desferrioxamine- and hypoxia-evoked HIF-1alpha accumulation--implications for prolyl hydroxylase activity and iron. Experimental cell research 20050515
Oligomycin inhibits HIF-1alpha expression in hypoxic tumor cells. American journal of physiology. Cell physiology 20050501
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Properties