Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110631
Identification
Name: N-acetyl-L-glutamate
Description:An N-acyl-L-α-amino acid anion resulting from deprotonation of both carboxy groups of N-acetyl-L-glutamic acid.
Structure
Thumb
Synonyms:
  • N-acetyl-L-glutamic acid
  • acetyl-L-glu
  • acetyl-L-glutamate
  • NAG
Chemical Formula: C7H9NO5
Average Molecular Weight: 187.15
Monoisotopic Molecular Weight: 189.0637224688
InChI Key: RFMMMVDNIPUKGG-YFKPBYRVSA-L
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)/p-2/t5-/m0/s1
CAS number: 1188-37-0
IUPAC Name:(2S)-2-acetamidopentanedioate
Traditional IUPAC Name: acetylglutamate
SMILES:CC(=O)NC(C([O-])=O)CCC(=O)[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as glutamic acid and derivatives. These 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent Glutamic 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
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • 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:
PropertyValueReference
Melting Point199 - 201 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility52 mg/mLNot Available
LogPNot AvailableNot Available
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: Not Available
Reactions:
Pathways: Not Available
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:
  • Pekkala S, Martínez AI, Barcelona B, Gallego J, Bendala E, Yefimenko I, Rubio V, Cervera J (2009)Structural insight on the control of urea synthesis: identification of the binding site for N-acetyl-L-glutamate, the essential allosteric activator of mitochondrial carbamoyl phosphate synthetase. The Biochemical journal 424, Pubmed: 19754428
  • Jia X, Ozawa K, Loscha K, Otting G (2009)Glutarate and N-acetyl-L-glutamate buffers for cell-free synthesis of selectively 15N-labelled proteins. Journal of biomolecular NMR 44, Pubmed: 19399372
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
CAS1188-37-0
ChEBI44337
ChemSpider1266066
HMDBHMDB01138
IAF126035520
KEGGC00624
MetaboLightsMTBLC44337
PubChem1549099