| Record Information |
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| Version | 2.0 |
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| Created at | 2007-04-12 20:38:27 UTC |
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| Updated at | 2021-08-19 20:22:31 UTC |
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| NP-MRD ID | NP0000060 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | N-Acetylglutamine |
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| Description | N-Acetylglutamine (NAcGln) is a modified amino acid (an acetylated analogue of glutamine) and is a metabolite present in normal human urine. The decomposition products of NAcGln have been identified by NMR and HPLC-MS as N-acetyl-L-glutamic acid, N-(2,6-dioxo-3-piperidinyl) acetamide, pyroglutamic acid, glutamic acid, and glutamine. NAcGln is used for parenteral nutrition as a source of glutamine since glutamine is too unstable whereas NAcGln is very stable. In patients treated with aminoglycosides and/or glycopeptides, an elevation of NAcGln in urine suggests renal tubular injury. High amounts of N-acetylated amino acids (i.E. N-acetylglutamine) were detected in a patient with aminoacylase I deficiency (EC 3.5.1.14, A homodimeric zinc-binding metalloenzyme located in the cytosol), a novel inborn error of metabolism (PMID:15331932 , 11312773 , 7952062 , 2569664 , 16274666 ). |
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| Structure | CC(=O)N[C@@H](CCC(N)=O)C(O)=O InChI=1S/C7H12N2O4/c1-4(10)9-5(7(12)13)2-3-6(8)11/h5H,2-3H2,1H3,(H2,8,11)(H,9,10)(H,12,13)/t5-/m0/s1 |
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| Synonyms | | Value | Source |
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| N~2~-acetyl-L-glutamine | ChEBI | | N-Acetyl-L-glutamine | HMDB | | Aceglutamide | HMDB | | Acetylglutamine | HMDB | | NAcGln | HMDB | | L-N2-Acetyl-glutamine | HMDB | | L-N2-Acetylglutamine | HMDB | | N2-Acetyl-L-glutamine | HMDB | | N2-Acetylglutamine | HMDB | | alpha-N-Acetyl-L-glutamine | HMDB | | Α-N-acetyl-L-glutamine | HMDB | | (2S)-2-Acetamido-5-amino-5-oxopentanoic acid | HMDB | | (2S)-4-Carbamoyl-2-acetamidobutanoic acid | HMDB | | N-Acetylglutamine | MeSH |
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| Chemical Formula | C7H12N2O4 |
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| Average Mass | 188.1812 Da |
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| Monoisotopic Mass | 188.07971 Da |
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| IUPAC Name | (2S)-4-carbamoyl-2-acetamidobutanoic acid |
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| Traditional Name | N-acetyl-L-glutamine |
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| CAS Registry Number | 2490-97-3 |
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| SMILES | CC(=O)N[C@@H](CCC(N)=O)C(O)=O |
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| InChI Identifier | InChI=1S/C7H12N2O4/c1-4(10)9-5(7(12)13)2-3-6(8)11/h5H,2-3H2,1H3,(H2,8,11)(H,9,10)(H,12,13)/t5-/m0/s1 |
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| InChI Key | KSMRODHGGIIXDV-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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| 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | 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 glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine 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 | Glutamine and derivatives |
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| Alternative Parents | |
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| Substituents | - Glutamine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- N-acyl-l-alpha-amino acid
- N-acyl-l-glutamine
- Fatty amide
- Fatty acyl
- Fatty acid
- Acetamide
- Carboxamide group
- Primary carboxylic acid amide
- Secondary carboxylic acid amide
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Organic nitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- 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 | - Van Coster RN, Gerlo EA, Giardina TG, Engelke UF, Smet JE, De Praeter CM, Meersschaut VA, De Meirleir LJ, Seneca SH, Devreese B, Leroy JG, Herga S, Perrier JP, Wevers RA, Lissens W: Aminoacylase I deficiency: a novel inborn error of metabolism. Biochem Biophys Res Commun. 2005 Dec 23;338(3):1322-6. Epub 2005 Nov 2. [PubMed:16274666 ]
- 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 ]
- Magnusson I, Kihlberg R, Alvestrand A, Wernerman J, Ekman L, Wahren J: Utilization of intravenously administered N-acetyl-L-glutamine in humans. Metabolism. 1989 Aug;38(8 Suppl 1):82-8. [PubMed:2569664 ]
- Bergana MM, Holton JD, Reyzer IL, Snowden MK, Baxter JH, Pound VL: NMR and MS analysis of decomposition compounds produced from N-acetyl-L-glutamine at low pH. J Agric Food Chem. 2000 Dec;48(12):6003-10. [PubMed:11312773 ]
- Racine SX, Le Toumelin P, Adnet F, Cohen Y, Cupa M, Hantz E, Le Moyec L: N-acetyl functions and acetate detected by nuclear magnetic resonance spectroscopy of urine to detect renal dysfunction following aminoglycoside and/or glycopeptide antibiotic therapy. Nephron Physiol. 2004;97(4):p53-7. [PubMed:15331932 ]
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