Record Information |
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Version | 2.0 |
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Creation Date | 2012-08-09 09:16:13 -0600 |
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Update Date | 2015-09-13 15:15:33 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | N-Acetylglutamic acid |
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Description | N-acetylglutamic acid is an acetylated amino acid. It is involved in arginine biosynthesis and is a substrate for both ArgA and ArgB in E. coli. |
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Structure | |
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Synonyms: | - 2-acetamido-L-Glutaraldehydate
- 2-acetamido-L-Glutaraldehydic acid
- Ac-Glu-OH
- Acetyl-glutamate
- Acetyl-glutamic acid
- Acetyl-L-glutamate
- Acetyl-L-glutamic acid
- Acetylglutamate
- Acetylglutamic acid
- DL-Acetylglutamate
- DL-Acetylglutamic acid
- N-Ac-Glu-OH
- N-acetyl L-glutamate
- N-acetyl L-glutamic acid
- N-Acetyl-DL-glutamate
- N-Acetyl-DL-glutamic acid
- N-acetyl-Glutamate
- N-acetyl-Glutamic acid
- N-Acetyl-L-glutamate
- N-Acetyl-L-glutamate-g-semialdehyde
- N-Acetyl-L-glutamate-gamma-semialdehyde
- N-Acetyl-L-glutamate-γ-semialdehyde
- N-Acetyl-L-glutamic acid
- N-Acetyl-L-glutamic acid-g-semialdehyde
- N-Acetyl-L-glutamic acid-gamma-semialdehyde
- N-Acetyl-L-glutamic acid-γ-semialdehyde
- N-Acetylglutamate
- N-Acetylglutamic g-semialdehyde
- N-Acetylglutamic gamma-semialdehyde
- N-Acetylglutamic γ-semialdehyde
- N-AcGlu
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Chemical Formula: | C7H11NO5 |
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Weight: | Average: 189.1659 Monoisotopic: 189.063722467 |
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InChI Key: | RFMMMVDNIPUKGG-UHFFFAOYSA-N |
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InChI: | 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) |
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CAS number: | 1188-37-0 |
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IUPAC Name: | (2S)-2-acetamidopentanedioic acid |
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Traditional IUPAC Name: | N-acetyl-L-glutamate |
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SMILES: | CC(=O)NC(CCC(O)=O)C(O)=O |
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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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Charge: | -2 |
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Melting point: | 199 - 201 °C |
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Experimental Properties: | Property | Value | Source |
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Water Solubility: | 52 mg/mL [HMP experimental] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | |
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KEGG Pathways: | |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-0a4i-1940000000-78ee4843d1eab79c7ca3 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0api-3930000000-e499004b087e5d741b02 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4j-0920000000-2d39b0eff0ff23756843 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0aor-1920000000-a2fe62d19e50f9db103f | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4j-0920000000-546571923f012476b58b | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0ap0-1910000000-d18f7c4035b189c1f4b6 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4r-1900000000-fc8347700abd012bf349 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9500000000-cdb488a97c5bf1952810 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-0900000000-1f9f80a37aa4e37ee878 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0fb9-0900000000-5423b76f7eb4b2a17fac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0udi-2900000000-38410c884a2999611065 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0zfr-9700000000-85acd9611312dd7df0db | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0pb9-9100000000-0d780e23d772cf133da2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-0ufr-1900000000-7a57de84cf9c6671cfc2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-0900000000-7b58c7204405ece93fca | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-1900000000-515b33cc5674fc8985c8 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-9300000000-b379a6e4d794e810c478 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-9000000000-2ce098bb9e1b35433878 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-9000000000-8e7d8abde262b7d5cb45 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-001i-1900000000-a3bdc3627857c5f47f4b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0ufr-2900000000-b074eaccd0b3864766b3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0fb9-0900000000-54faa7b7182f5cceca84 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-001i-6900000000-0f14d0a7c8fb67a381b2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-053r-9000000000-333b6aa44450dbd0c754 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-001i-9100000000-adf2d3645b4231cbddc3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-001i-2900000000-d7df112ff7af7e076d70 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0536-9000000000-d70c37086adaa1636750 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-006x-0900000000-88345aaf9776c7fb8676 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udl-2900000000-5fca3bd987ebf6b42946 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udj-9500000000-be58124b136b37456414 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-a56ffb8d475d132443a8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004v-2900000000-c32612499c0a2ceb8298 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9300000000-75dbbc130d00cfec5880 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - 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
- 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
- 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
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
- 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
- Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
- 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
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Synthesis Reference: | hang, Xiaolin; Yang, Qiyong; Sun, Yuesheng. Preparation of N-acetyl-L-glutamic acid. Huaxue Shijie (2002), 43(7), 363-365. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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