Home Aminos (2S)-2-Amino-5-[(N,N'-dimethylcarbamimidoyl)amino]pentanoic acid

(2S)-2-Amino-5-[(N,N'-dimethylcarbamimidoyl)amino]pentanoic acid

CAS No.:
30344-00-4
Catalog Number:
AG002ZU2
Molecular Formula:
C8H18N4O2
Molecular Weight:
202.2541
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
10mg
98%
1 week
United States
$157
- +
25mg
98%
1 week
United States
$257
- +
50mg
98%
1 week
United States
$373
- +
250mg
95%
1 week
United States
$382
- +
1g
95%
1 week
United States
$900
- +
Product Description
Catalog Number:
AG002ZU2
Chemical Name:
(2S)-2-Amino-5-[(N,N'-dimethylcarbamimidoyl)amino]pentanoic acid
CAS Number:
30344-00-4
Molecular Formula:
C8H18N4O2
Molecular Weight:
202.2541
MDL Number:
MFCD14705169
IUPAC Name:
(2S)-2-amino-5-[(N,N'-dimethylcarbamimidoyl)amino]pentanoic acid
InChI:
InChI=1S/C8H18N4O2/c1-10-8(11-2)12-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H,13,14)(H2,10,11,12)/t6-/m0/s1
InChI Key:
HVPFXCBJHIIJGS-LURJTMIESA-N
SMILES:
CNC(=NC)NCCC[C@@H](C(=O)O)N
UNII:
49787G1ULV
Properties
Complexity:
206  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
202.143g/mol
Formal Charge:
0
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
202.258g/mol
Monoisotopic Mass:
202.143g/mol
Rotatable Bond Count:
7  
Topological Polar Surface Area:
99.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.7  
Literature
Title Journal
INF-β1b therapy modulates L-arginine and nitric oxide metabolism in patients with relapse remittent multiple sclerosis. Journal of the neurological sciences 20121215
Birth by cesarean section is associated with elevated neonatal plasma levels of dimethylarginines. Pediatrics international : official journal of the Japan Pediatric Society 20120801
Osteopontin and symmetric dimethylarginine plasma levels in solitary functioning kidney in children. Acta paediatrica (Oslo, Norway : 1992) 20120801
Diagnostical significance of dimethylarginine in the development of hepatorenal syndrome in patients with alcoholic liver cirrhosis. Vojnosanitetski pregled 20120801
Nitric oxide synthase, ADMA, SDMA, and nitric oxide activity in the paraventricular nucleus throughout the etiology of renal wrap hypertension. American journal of physiology. Heart and circulatory physiology 20120601
Endogenous nitric oxide synthase inhibitors in the biology of disease: markers, mediators, and regulators? Arteriosclerosis, thrombosis, and vascular biology 20120601
Asymmetric dimethylarginine in adults with cystathionine β-synthase deficiency. Atherosclerosis 20120601
Elevation of serum asymmetrical and symmetrical dimethylarginine in patients with advanced glaucoma. Investigative ophthalmology & visual science 20120418
Is plasma symmetric dimethylarginine a suitable marker of renal function in children and adolescents? Scandinavian journal of urology and nephrology 20120201
The combined ratios of L-arginine and asymmetric and symmetric dimethylarginine as biomarkers in spontaneously hypertensive rats. Translational research : the journal of laboratory and clinical medicine 20120201
Optimization of the separation of NDA-derivatized methylarginines by capillary and microchip electrophoresis. Journal of laboratory automation 20120201
Lack of association between asymmetric dimethylarginine and in vivo microvascular and macrovascular endothelial function in patients with rheumatoid arthritis. Clinical and experimental rheumatology 20120101
Diagnostic value of plasma asymmetric and symmetric dimethylarginine levels in liver transplant recipients. Polskie Archiwum Medycyny Wewnetrznej 20120101
Binding of the heterogeneous ribonucleoprotein K (hnRNP K) to the Epstein-Barr virus nuclear antigen 2 (EBNA2) enhances viral LMP2A expression. PloS one 20120101
Parental history of premature coronary artery disease does not affect plasma levels of asymmetric dimethylarginine in young healthy adults. Polskie Archiwum Medycyny Wewnetrznej 20120101
Increased asymmetric dimethylarginine and enhanced inflammation are associated with impaired vascular reactivity in women with endometriosis. Atherosclerosis 20111201
Adenosine A₁-receptor deficiency diminishes afferent arteriolar and blood pressure responses during nitric oxide inhibition and angiotensin II treatment. American journal of physiology. Regulatory, integrative and comparative physiology 20111201
The biological effect of pharmacological treatment on dimethylaminohydrolases (DDAH-1) and cationic amino acid transporter-1 (CAT-1) expression in patients with acute congestive heart failure. Microvascular research 20111101
Plasma symmetric dimethylarginine reference limits from the Framingham offspring cohort. Clinical chemistry and laboratory medicine 20111101
Asymmetric dimethylarginine is increased in asthma. American journal of respiratory and critical care medicine 20111001
Asymmetric dimethylarginine predicts appropriate implantable cardioverter-defibrillator intervention in patients with left ventricular dysfunction. Europace : European pacing, arrhythmias, and cardiac electrophysiology : journal of the working groups on cardiac pacing, arrhythmias, and cardiac cellular electrophysiology of the European Society of Cardiology 20111001
Symmetric dimethylarginine as a proinflammatory agent in chronic kidney disease. Clinical journal of the American Society of Nephrology : CJASN 20111001
Salt sensitivity in blacks: evidence that the initial pressor effect of NaCl involves inhibition of vasodilatation by asymmetrical dimethylarginine. Hypertension (Dallas, Tex. : 1979) 20110901
Systemic inflammation is linked to low arginine and high ADMA plasma levels resulting in an unfavourable NOS substrate-to-inhibitor ratio: the Hoorn Study. Clinical science (London, England : 1979) 20110701
Symmetric dimethylarginine (SDMA) is raised in women with polycystic ovary syndrome: a pilot study. Journal of obstetrics and gynaecology : the journal of the Institute of Obstetrics and Gynaecology 20110701
Plasma levels of asymmetric dimethylarginine in patients with biopsy-proven nonalcoholic fatty liver disease. Metabolism: clinical and experimental 20110601
Plasma dimethylarginines during the acute inflammatory response. European journal of clinical investigation 20110601
Simultaneous gas chromatography-tandem mass spectrometry quantification of symmetric and asymmetric dimethylarginine in human urine. Analytical biochemistry 20110601
Effects of coronary revascularization with or without cardiopulmonary bypass on plasma levels of asymmetric dimethylarginine. Coronary artery disease 20110601
The role of asymmetric and symmetric dimethylarginines in renal disease. Nature reviews. Nephrology 20110501
Asymmetric dimethylarginine as a risk factor for cardiovascular disease in Japanese patients with type 2 diabetes mellitus. Clinical endocrinology 20110401
[Role of arginine methylation in the Piwi-interacting RNA pathway]. Seikagaku. The Journal of Japanese Biochemical Society 20110401
Asymmetric dimethylarginine as an independent risk marker for mortality in ambulatory patients with peripheral arterial disease. Journal of internal medicine 20110301
Posttranslational arginine methylation of lamin A/C during myoblast fusion. Biochimica et biophysica acta 20110201
Time course of asymmetric dimethylarginine (ADMA) and oxidative stress in fructose-hypertensive rats: a model related to metabolic syndrome. Atherosclerosis 20110201
The alteration of asymmetric dimetilarginine (ADMA) levels in cardiac and gastrocnemius muscles following radioactive iodine application in guinea pigs and the effect of L-carnitine on this alteration. International journal of radiation biology 20110101
Symmetrical and asymmetrical dimethylarginine as predictors for mortality in patients referred for coronary angiography: the Ludwigshafen Risk and Cardiovascular Health study. Clinical chemistry 20110101
Symmetrical dimethylarginine outperforms CKD-EPI and MDRD-derived eGFR for the assessment of renal function in patients with adult congenital heart disease. Kidney & blood pressure research 20110101
Production of free methylarginines via the proteasome and autophagy pathways in cultured cells. Molecular medicine reports 20110101
Quantitation of L-arginine and asymmetric dimethylarginine in human plasma by LC-selective ion mode-MS for Type 2 diabetes mellitus study. Chemical & pharmaceutical bulletin 20110101
Simultaneous determination of L-arginine, asymmetric dimethylarginine, and symmetric dimethylarginine in the plasma of rodents with LC-MS/MS. Arzneimittel-Forschung 20110101
Negative association of L-arginine methylation products with oocyte numbers. Human reproduction (Oxford, England) 20101201
HPLC determination of plasma dimethylarginines: method validation and preliminary clinical application. Clinica chimica acta; international journal of clinical chemistry 20101111
Relationships between dimethylarginine and the presence of vertebral fractures in type 2 diabetes mellitus. Clinical endocrinology 20101001
Immunolocalisation and activity of DDAH I and II in the heart and modification post-myocardial infarction. Acta histochemica 20100901
Structural basis for methylarginine-dependent recognition of Aubergine by Tudor. Genes & development 20100901
Synergistic effects of asymmetrical dimethyl-L-arginine accumulation and endothelial progenitor cell deficiency on renal function decline during a 2-year follow-up in stable angina. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20100801
Plasma asymmetric dimethylarginine concentrations in sickle cell disease are related to the hemolytic phenotype. Blood cells, molecules & diseases 20100415
Increased nitric oxide stress is associated with migraine. Cephalalgia : an international journal of headache 20100401
Effects of stent implementation on plasma levels of asymmetric dimethylarginine in patients with or without ST-segment elevation acute myocardial infarction. International journal of molecular medicine 20100401
The efficacy of oral beraprost sodium, a prostaglandin I2 analogue, for treating intermittent claudication in patients with arteriosclerosis obliterans. International angiology : a journal of the International Union of Angiology 20100401
How does the royal family of Tudor rule the PIWI-interacting RNA pathway? Genes & development 20100401
Symmetric dimethylarginine predicts all-cause mortality following ischemic stroke. Atherosclerosis 20100201
Symmetric dimethylarginine, an endogenous marker of glomerular filtration rate, and the risk for microalbuminuria in young people with type 1 diabetes. Archives of disease in childhood 20100201
Treatment with alpha-lipoic acid reduces asymmetric dimethylarginine in patients with type 2 diabetes mellitus. Translational research : the journal of laboratory and clinical medicine 20100101
The effect of n-3 fatty acids on levels of methylarginines in patients with end-stage renal disease. Journal of nephrology 20100101
Effect of simvastatin on nitric oxide synthases (eNOS, iNOS) and arginine and its derivatives (ADMA, SDMA) in ischemia/reperfusion injury in rat liver. Pharmacological reports : PR 20100101
Taxane-based adjuvant chemotherapy reduces endothelin-1 and symmetric dimethylarginine levels in patients with breast cancer. Journal of B.U.ON. : official journal of the Balkan Union of Oncology 20100101
Methylarginines and mortality in patients with end stage renal disease: a prospective cohort study. Atherosclerosis 20091201
Dimethylarginines and serotonin in the blood of spontaneously hypertensive rats. Bulletin of experimental biology and medicine 20091201
Nested case-control study of one-carbon metabolites in mid-pregnancy and risks of cleft lip with and without cleft palate. Pediatric research 20091101
Diabetic retinopathy is associated with elevated serum asymmetric and symmetric dimethylarginines. Diabetes care 20091101
Dimethylarginine levels in cerebrospinal fluid of hyperacute ischemic stroke patients are associated with stroke severity. Neurochemical research 20090901
Targeted metabolomic evaluation of arginine methylation and cardiovascular risks: potential mechanisms beyond nitric oxide synthase inhibition. Arteriosclerosis, thrombosis, and vascular biology 20090901
Haemodialysis acutely reduces the plasma levels of ADMA without reversing impaired NO-dependent vasodilation. Clinical science (London, England : 1979) 20090824
ADMA and SDMA levels in healthy men exposed to tobacco smoke. Atherosclerosis 20090801
Asymmetric and symmetric dimethylarginines are of similar predictive value for cardiovascular risk in the general population. Atherosclerosis 20090701
Polycystic ovary syndrome is associated with severe platelet and endothelial dysfunction in both obese and lean subjects. Atherosclerosis 20090601
Role of symmetric dimethylarginine in vascular damage by increasing ROS via store-operated calcium influx in monocytes. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20090501
Endogenous nitric oxide synthase inhibitors in sickle cell disease: abnormal levels and correlations with pulmonary hypertension, desaturation, haemolysis, organ dysfunction and death. British journal of haematology 20090501
Asymmetric dimethylarginine, oxidative stress, and vascular nitric oxide synthase in essential hypertension. American journal of physiology. Regulatory, integrative and comparative physiology 20090201
Blood content of asymmetric dimethylarginine: new insights into its dysregulation in renal disease. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20090201
Randomized placebo-controlled trial assessing a treatment strategy consisting of pravastatin, vitamin E, and homocysteine lowering on plasma asymmetric dimethylarginine concentration in mild to moderate CKD. American journal of kidney diseases : the official journal of the National Kidney Foundation 20090101
Unchanged plasma levels of dimethylarginines and nitric oxide in chronic hepatitis C. Scandinavian journal of gastroenterology 20090101
Asymmetric dimethylarginine and symmetric dimethylarginine: axis of evil or useful alliance? Seminars in dialysis 20090101
The emerging role of symmetric dimethylarginine in vascular disease. Advances in clinical chemistry 20090101
Dimethylarginine levels and nutritional status in hemodialysis patients. Journal of nephrology 20090101
Effects of an exercise intervention using Dance Dance Revolution on endothelial function and other risk factors in overweight children. International journal of pediatric obesity : IJPO : an official journal of the International Association for the Study of Obesity 20090101
Transjugular intrahepatic portosystemic shunt-placement increases arginine/asymmetric dimethylarginine ratio in cirrhotic patients. World journal of gastroenterology 20081221
Asymmetric dimethylarginine in hematological malignancies: a preliminary study. Leukemia & lymphoma 20081201
Development and validation of a fast quantitative method for plasma dimethylarginines analysis using liquid chromatography-tandem mass spectrometry. Clinical biochemistry 20081101
Asymmetric dimethylarginine and coronary collateral vessel development. Coronary artery disease 20081101
Asymmetric dimethylarginine (ADMA) is tightly correlated with growth in juveniles without correlations to obesity related disorders. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association 20081001
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Symmetric dimethylarginine is an independent predictor of intradialytic hypotension. American journal of hypertension 20080801
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Role of nitric oxide deficiency in the development of hypertension in hydronephrotic animals. American journal of physiology. Renal physiology 20080201
ADMA levels correlate with proteinuria, secondary amyloidosis, and endothelial dysfunction. Journal of the American Society of Nephrology : JASN 20080201
Plasma asymmetric dimethylarginine, symmetric dimethylarginine, l-arginine, and nitrite/nitrate concentrations in cats with chronic kidney disease and hypertension. Journal of veterinary internal medicine 20080101
Nebivolol reduces asymmetric dimethylarginine in endothelial cells by increasing dimethylarginine dimethylaminohydrolase 2 (DDAH2) expression and activity. Pharmacological research 20071201
Assessment of protein-incorporated arginine methylation in biological specimens by CZE UV-detection. Electrophoresis 20071201
Prenatal increased asymmetric dimethylarginine is associated with placental heat-shock protein 70 and lectin-like oxidized low-density lipoprotein receptor-1 expression. Archives of medical research 20071101
AS1411 alters the localization of a complex containing protein arginine methyltransferase 5 and nucleolin. Cancer research 20071101
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The lung in the balance: arginine, methylated arginines, and nitric oxide. American journal of physiology. Lung cellular and molecular physiology 20070101
Plasma asymmetric dimethylarginine concentration during the perinatal period. Neonatology 20070101
Plasma dimethylarginine levels in chronic hemodialysis patients are independent of the type of dialyzer applied. Blood purification 20070101
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High-performance liquid chromatographic assay of asymmetric dimethylarginine, symmetric dimethylarginine, and arginine in human plasma by derivatization with naphthalene-2,3-dicarboxaldehyde. Analytical biochemistry 20030701
Asymmetric dimethylarginine and total homocysteine in plasma after oral methionine loading. Scandinavian journal of clinical and laboratory investigation 20030101
Leptin improves membrane fluidity of erythrocytes in humans via a nitric oxide-dependent mechanism--an electron paramagnetic resonance investigation. Biochemical and biophysical research communications 20020927
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Probucol preserves endothelial function by reduction of the endogenous nitric oxide synthase inhibitor level. British journal of pharmacology 20020301
Endogenous nitric oxide synthase inhibitors in endothelial cells, endothelin-1 within the vessel wall, and intimal hyperplasia in perimenopausal human uterine arteries. Journal of cardiovascular pharmacology 20020201
Homocysteine impairs the nitric oxide synthase pathway: role of asymmetric dimethylarginine. Circulation 20011120
Renin-angiotensin system is involved in the mechanism of increased serum asymmetric dimethylarginine in essential hypertension. Japanese circulation journal 20010901
Endothelium-dependent vasodilation is independent of the plasma L-arginine/ADMA ratio in men with stable angina: lack of effect of oral L-arginine on endothelial function, oxidative stress and exercise performance. Journal of the American College of Cardiology 20010801
Serum concentrations of asymmetric (ADMA) and symmetric (SDMA) dimethylarginine in renal failure patients. Kidney international. Supplement 20010201
Increased reduction of dimethylarginines and lowered interdialytic blood pressure by the use of biocompatible membranes. Kidney international. Supplement 20010201
Properties