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1188-38-1

1188-38-1 | N-Carbamyl-L-glutamic acid

CAS No: 1188-38-1 Catalog No: AG003868 MDL No:MFCD00047874

Product Description

Catalog Number:
AG003868
Chemical Name:
N-Carbamyl-L-glutamic acid
CAS Number:
1188-38-1
Molecular Formula:
C6H10N2O5
Molecular Weight:
190.1540
MDL Number:
MFCD00047874
IUPAC Name:
(2S)-2-(carbamoylamino)pentanedioic acid
InChI:
InChI=1S/C6H10N2O5/c7-6(13)8-3(5(11)12)1-2-4(9)10/h3H,1-2H2,(H,9,10)(H,11,12)(H3,7,8,13)/t3-/m0/s1
InChI Key:
LCQLHJZYVOQKHU-VKHMYHEASA-N
SMILES:
OC(=O)CC[C@@H](C(=O)O)NC(=O)N
UNII:
5L0HB4V1EW

Properties

Complexity:
227  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
190.059g/mol
Formal Charge:
0
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
190.155g/mol
Monoisotopic Mass:
190.059g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
130A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.4  

Literature

Title Journal
Effects of dietary L-arginine or N-carbamylglutamate supplementation during late gestation of sows on the miR-15b/16, miR-221/222, VEGFA and eNOS expression in umbilical vein. Amino acids 20120601
A novel biochemically salvageable animal model of hyperammonemia devoid of N-acetylglutamate synthase. Molecular genetics and metabolism 20120601
Effect of dietary arginine and N-carbamoylglutamate supplementation on reproduction and gene expression of eNOS, VEGFA and PlGF1 in placenta in late pregnancy of sows. Animal reproduction science 20120601
N-carbamylglutamate enhances pregnancy outcome in rats through activation of the PI3K/PKB/mTOR signaling pathway. PloS one 20120101
N-carbamylglutamate enhancement of ureagenesis leads to discovery of a novel deleterious mutation in a newly defined enhancer of the NAGS gene and to effective therapy. Human mutation 20111001
The HepaRG cell line is suitable for bioartificial liver application. The international journal of biochemistry & cell biology 20111001
Down-regulation of hepatic urea synthesis by oxypurines: xanthine and uric acid inhibit N-acetylglutamate synthase. The Journal of biological chemistry 20110624
N-carbamylglutamate treatment for acute neonatal hyperammonemia in isovaleric acidemia. European journal of pediatrics 20110601
New developments in the treatment of hyperammonemia: emerging use of carglumic acid. International journal of general medicine 20110101
MR spectroscopy-based brain metabolite profiling in propionic acidaemia: metabolic changes in the basal ganglia during acute decompensation and effect of liver transplantation. Orphanet journal of rare diseases 20110101
Role of carglumic acid in the treatment of acute hyperammonemia due to N-acetylglutamate synthase deficiency. Therapeutics and clinical risk management 20110101
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20101201
Dietary supplementation with L-arginine or N-carbamylglutamate enhances intestinal growth and heat shock protein-70 expression in weanling pigs fed a corn- and soybean meal-based diet. Amino acids 20100801
N-carbamylglutamate augments ureagenesis and reduces ammonia and glutamine in propionic acidemia. Pediatrics 20100701
Carglumic acid approved to treat genetic hyperammonemia. American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20100501
Outpatient treatment of propionic acidemia-associated hyperammonemia with N-carbamoyl-L-glutamate in an infant. Clinical therapeutics 20100401
Favourable long-term outcome after immediate treatment of neonatal hyperammonemia due to N-acetylglutamate synthase deficiency. European journal of pediatrics 20100201
Biochemical efficacy of N-carbamylglutamate in neonatal severe hyperammonaemia due to propionic acidaemia. European journal of pediatrics 20100101
N-carbamylglutamate in emergency management of hyperammonemia in neonatal acute onset propionic and methylmalonic aciduria. Neonatology 20100101
N-acetylglutamate synthase: structure, function and defects. Molecular genetics and metabolism 20100101
Effects of a single dose of N-carbamylglutamate on the rate of ureagenesis. Molecular genetics and metabolism 20091201
[N-carbamyl glutamate treatment in hyperammoniemia decompensated propionic acidaemia]. Anales de pediatria (Barcelona, Spain : 2003) 20091201
The first use of N-carbamylglutamate in a patient with decompensated maple syrup urine disease. Metabolic brain disease 20090901
Pricing of orphan drugs. Lancet (London, England) 20090207
Uncovering metabolic pathways relevant to phenotypic traits of microbial genomes. Genome biology 20090101
N-carbamylglutamate for neonatal hyperammonaemia in propionic acidaemia. Journal of inherited metabolic disease 20081201
N-carbamylglutamate markedly enhances ureagenesis in N-acetylglutamate deficiency and propionic acidemia as measured by isotopic incorporation and blood biomarkers. Pediatric research 20080801
[A newborn infant with hyperventilation]. Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke 20080626
Carglumic acid: a second look. Confirmed progress in a rare urea cycle disorder. Prescrire international 20080401
Carglumic acid: an additional therapy in the treatment of organic acidurias with hyperammonemia? Orphanet journal of rare diseases 20080101
Mutations and polymorphisms in the human N-acetylglutamate synthase (NAGS) gene. Human mutation 20070801
A trial with N-carbamylglutamate may not detect all patients with NAGS deficiency and neonatal onset. Journal of inherited metabolic disease 20070601
Metabolic fates of ammonia-N in ruminal epithelial and duodenal mucosal cells isolated from growing sheep. Journal of dairy science 20051101
Neonatal hyperammonemia: the N-carbamoyl-L-glutamic acid test. The Journal of pediatrics 20050801
Misleading diagnosis of partial N-acetylglutamate synthase deficiency based on enzyme measurement corrected by mutation analysis. Acta paediatrica (Oslo, Norway : 1992) 20050101
N-carbamylglutamate protects patients with decompensated propionic aciduria from hyperammonaemia. Journal of inherited metabolic disease 20050101
Restoration of ureagenesis in N-acetylglutamate synthase deficiency by N-carbamylglutamate. The Journal of pediatrics 20041001
Urea synthesis by ruminal epithelial and duodenal mucosal cells from growing sheep. Journal of dairy science 20040601
Mammalian N-acetylglutamate synthase. Molecular genetics and metabolism 20040401
Carglumic acid: new preparation. An advance in rare urea cycle disorders. Prescrire international 20040201
Hyperammonaemia as a cause of psychosis in an adolescent. European journal of pediatrics 20031101
N-carbamylglutamate enhances ammonia detoxification in a patient with decompensated methylmalonic aciduria. Molecular genetics and metabolism 20030801
N-acetylglutamate synthase deficiency and the treatment of hyperammonemic encephalopathy. Annals of neurology 20021201
Mixture of N-carbamoyl-L-glutamate plus L-arginine can protect rats with liver cirrhosis from acute ammonia intoxication. Journal of hepatology 20011201
Hyperinsulinism and hyperammonemia syndrome: report of twelve unrelated patients. Pediatric research 20010901
[Orphan drugs and metabolic disorders]. Revista de neurologia 20010801

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