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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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