| Record Information |
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| Version | 2.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2024-09-17 15:42:07 UTC |
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| NP-MRD ID | NP0000536 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | N-Acetylglutamic acid |
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| Description | N-acetyl-L-glutamic acid, also known as N-acetylglutamate (abbreviated NAG) belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-acetyl-L-glutamic acid is an N-acyl-L-amino acid that is L-glutamic acid in which one of the amine hydrogens is substituted by an acetyl group. N-acetyl-L-glutamic acid is biosynthesized from glutamate and acetylornithine by ornithine acetyltransferase, and from glutamic acid and acetyl-CoA by the enzyme N-acetylglutamate synthase. The reverse reaction, hydrolysis of the acetyl group, is catalyzed by a specific hydrolase. It is the first intermediate involved in the biosynthesis of arginine in prokaryotes and simple eukaryotes and a regulator in the process known as the urea cycle that converts toxic ammonia to urea for excretion from the body in vertebrates. N-Acetyl-L-glutamic acid exists in all living species, ranging from bacteria to humans. In vertebrae and mammals, N-acetylglutamic acid is the allosteric activator molecule to mitochondrial carbamyl phosphate synthetase I (CPSI) which is the first enzyme in the urea cycle. It triggers the production of the first urea cycle intermediate, carbamyl phosphate. CPSI is inactive when N-acetylglutamic acid is not present. In the liver and small intestines, N-acetylglutamic acid-dependent CPSI produces citrulline, the second intermediate in the urea cycle. N-acetylglutamic acid concentrations increase when protein consumption increases due to the accumulation of ammonia that must be secreted through the urea cycle, which supports the role of N-acetylglutamic acid as the cofactor for CPSI. Furthermore, N-acetylglutamic acid can be found in many commonly consumed foods such as soy, corn, and coffee, with cocoa powder containing a notably high concentration. Deficiency in N-acetylglutamic acid in humans is an autosomal recessive disorder that results in blockage of urea production which ultimately increases the concentration of ammonia in the blood (hyperammonemia). This can be caused by defects in the NAGS coding gene or by deficiencies in the precursors essential for its synthesis. |
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| Structure | CC(=O)N[C@@H](CCC(O)=O)C(O)=O InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1 |
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| Synonyms | | Value | Source |
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| (S)-2-(Acetylamino)pentanedioic acid | ChEBI | | Ac-glu-OH | ChEBI | | Acetyl-L-glutamic acid | ChEBI | | Acetylglutamic acid | ChEBI | | L-N-Acetylglutamic acid | ChEBI | | N-Ac-glu-OH | ChEBI | | N-ACETYL-L-glutamATE | ChEBI | | N-Acetylglutamic acid | ChEBI | | (S)-2-(Acetylamino)pentanedioate | Generator | | Acetyl-L-glutamate | Generator | | Acetylglutamate | Generator | | L-N-Acetylglutamate | Generator | | N-Acetylglutamate | Generator | | N-Acetylglutamic acid semialdehyde | HMDB | | N-Acetylglutamate, potassium salt, (L)-isomer | HMDB | | N-Acetylglutamate, (D)-isomer | HMDB | | N-Acetylglutamate, calcium salt (1:1), (L)-isomer | HMDB | | N-Acetylglutamate, dipotassium salt, (L)-isomer | HMDB | | N-Acetylglutamate, disodium salt, (L)-isomer | HMDB | | N-Acetylglutamate, calcium salt, (L)-isomer | HMDB | | N-Acetylglutamate, magnesium salt, (L)-isomer | HMDB | | Sodium N-acetylglutamate | HMDB | | N-Acetylglutamate, (DL)-isomer | HMDB | | N-Acetylglutamate, monosodium salt, (L)-isomer | HMDB | | N-Acetyl-L-glutaminic acid | HMDB | | alpha-(N-Acetyl)-L-glutamic acid | HMDB | | Α-(N-acetyl)-L-glutamic acid | HMDB | | NAcGlu | HMDB | | N-Acetyl-L-glutamic acid | Generator, KEGG |
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| Chemical Formula | C7H11NO5 |
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| Average Mass | 189.1659 Da |
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| Monoisotopic Mass | 189.06372 Da |
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| IUPAC Name | (2S)-2-acetamidopentanedioic acid |
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| Traditional Name | N-acetyl-L-glutamate |
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| CAS Registry Number | 1188-37-0 |
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| SMILES | CC(=O)N[C@@H](CCC(O)=O)C(O)=O |
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| InChI Identifier | InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1 |
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| InChI Key | RFMMMVDNIPUKGG-YFKPBYRVSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Glutamic acid and derivatives |
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| Alternative Parents | |
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| Substituents | - Glutamic acid or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Dicarboxylic acid or derivatives
- Fatty acid
- Carboximidic acid
- Carboximidic acid derivative
- Carboxylic acid
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carbonyl group
- Organonitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | |
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| Predicted Properties | |
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| General References | - Zhang W, Holzknecht RA, Butkowski RJ, Tuchman M: Immunochemical analysis of carbamyl phosphate synthetase I and ornithine transcarbamylase deficient livers: elevated N-acetylglutamate level in a liver lacking carbamyl phosphate synthetase protein. Clin Invest Med. 1990 Aug;13(4):183-8. [PubMed:2208834 ]
- Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]
- Sugahara K, Zhang J, Kodama H: Liquid chromatographic-mass spectrometric analysis of N-acetylamino acids in human urine. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):15-21. [PubMed:7952062 ]
- Tuchman M, Holzknecht RA: N-acetylglutamate content in liver and gut of normal and fasted mice, normal human livers, and livers of individuals with carbamyl phosphate synthetase or ornithine transcarbamylase deficiency. Pediatr Res. 1990 Apr;27(4 Pt 1):408-12. [PubMed:2342831 ]
- Vockley J, Vockley CM, Lin SP, Tuchman M, Wu TC, Lin CY, Seashore MR: Normal N-acetylglutamate concentration measured in liver from a new patient with N-acetylglutamate synthetase deficiency: physiologic and biochemical implications. Biochem Med Metab Biol. 1992 Feb;47(1):38-46. [PubMed:1562355 ]
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