N-Acetylglutamic acid (PAMDB001824)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001824
Identification
Name: N-Acetylglutamic acid
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 Pseudomonas aeruginosa.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 189.1659
Monoisotopic Molecular Weight: 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:2-acetamidopentanedioic acid
Traditional IUPAC Name: acetylglutamate
SMILES:CC(=O)NC(CCC(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent N-acyl-aliphatic-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
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 mg/mLALOGPS
logP-0.67ALOGPS
logP-1.1ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.73 m3·mol-1ChemAxon
Polarizability17.28 Å3ChemAxon
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
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-006y-0900000000-253a2008e5434e261a26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9600000000-784f477a051434e9ba82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-053u-9000000000-3f296192137041b66c1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-5900000000-9cc96458c06943e10820View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0ug0-0900000000-00353ebbdcea9aaf232dView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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