N-Acetylglutamic acid (ECMDB21429) (M2MDB001824)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (910)
Record Information
Version2.0
Creation Date2012-08-09 09:16:13 -0600
Update Date2015-09-13 15:15:33 -0600
Secondary Accession Numbers
  • ECMDB21429
Identification
Name:N-Acetylglutamic acid
DescriptionN-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.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
Chemical Formula:C7H11NO5
Weight:Average: 189.1659
Monoisotopic: 189.063722467
InChI Key:RFMMMVDNIPUKGG-UHFFFAOYSA-N
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)
CAS number:1188-37-0
IUPAC Name:(2S)-2-acetamidopentanedioic acid
Traditional IUPAC Name:N-acetyl-L-glutamate
SMILES:CC(=O)NC(CCC(O)=O)C(O)=O
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:199 - 201 °C
Experimental Properties:
PropertyValueSource
Water Solubility:52 mg/mL [HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility18.6 g/LALOGPS
logP-0.67ALOGPS
logP-1.1ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.73 m³·mol⁻¹ChemAxon
Polarizability17.44 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Acetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid
N-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP
L-Glutamic acid + Acetyl-CoA + L-Glutamate > Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetylglutamic acid
N-Acetylglutamic acid + Adenosine triphosphate + N-Acetylglutamic acid > Adenosine diphosphate + N-Acetyl-L-glutamyl 5-phosphate + ADP
Acetyl-CoA + L-Glutamic acid + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetyl-L-alanine + N-Acetylglutamic acid
Acetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid
N-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP
SMPDB Pathways:
L-glutamate metabolism IIPW001886 ThumbThumb?image type=greyscaleThumb?image type=simple
arginine metabolismPW000790 ThumbThumb?image type=greyscaleThumb?image type=simple
ornithine metabolismPW000791 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4i-1940000000-78ee4843d1eab79c7ca3View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0api-3930000000-e499004b087e5d741b02View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4j-0920000000-2d39b0eff0ff23756843View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aor-1920000000-a2fe62d19e50f9db103fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4j-0920000000-546571923f012476b58bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ap0-1910000000-d18f7c4035b189c1f4b6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4r-1900000000-fc8347700abd012bf349View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-cdb488a97c5bf1952810View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-1f9f80a37aa4e37ee878View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fb9-0900000000-5423b76f7eb4b2a17facView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-2900000000-38410c884a2999611065View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0zfr-9700000000-85acd9611312dd7df0dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0pb9-9100000000-0d780e23d772cf133da2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0ufr-1900000000-7a57de84cf9c6671cfc2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-7b58c7204405ece93fcaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-1900000000-515b33cc5674fc8985c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9300000000-b379a6e4d794e810c478View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-2ce098bb9e1b35433878View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-8e7d8abde262b7d5cb45View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1900000000-a3bdc3627857c5f47f4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-2900000000-b074eaccd0b3864766b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0fb9-0900000000-54faa7b7182f5cceca84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-6900000000-0f14d0a7c8fb67a381b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-053r-9000000000-333b6aa44450dbd0c754View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-adf2d3645b4231cbddc3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-d7df112ff7af7e076d70View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0536-9000000000-d70c37086adaa1636750View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-88345aaf9776c7fb8676View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-2900000000-5fca3bd987ebf6b42946View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-9500000000-be58124b136b37456414View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a56ffb8d475d132443a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004v-2900000000-c32612499c0a2ceb8298View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-75dbbc130d00cfec5880View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
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
Synthesis Reference:hang, Xiaolin; Yang, Qiyong; Sun, Yuesheng. Preparation of N-acetyl-L-glutamic acid. Huaxue Shijie (2002), 43(7), 363-365.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID12575
HMDB IDHMDB01138
Pubchem Compound ID185
Kegg IDC00624
ChemSpider ID180
WikipediaN-Acetylglutamic acid
BioCyc IDNot Available

Enzymes

Protein Details
1. Amino-acid acetyltransferase
General function:
Involved in cellular amino acid biosynthetic process
Specific function:
Acetyl-CoA + L-glutamate = CoA + N-acetyl-L- glutamate
Gene Name:
argA
Uniprot ID:
P0A6C5
Molecular weight:
49195
Reactions
Acetyl-CoA + L-glutamate = CoA + N-acetyl-L-glutamate.
Protein Details
2. Acetylglutamate kinase
General function:
Involved in acetylglutamate kinase activity
Specific function:
ATP + N-acetyl-L-glutamate = ADP + N-acetyl-L- glutamate 5-phosphate
Gene Name:
argB
Uniprot ID:
P0A6C8
Molecular weight:
27159
Reactions
ATP + N-acetyl-L-glutamate = ADP + N-acetyl-L-glutamate 5-phosphate.