N-Acetylglutamic acid

N-Acetylglutamic acid
Skeletal formula of N-acetylglutamic acid
Names
IUPAC name
2-Acetamidopentanedioic acid[1]
Other names
Acetylglutamic acid[citation needed]
Identifiers
3D model (JSmol)
3DMet
Abbreviations
1727473 S
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.024.899 Edit this at Wikidata
EC Number
  • 227-388-6
KEGG
MeSH N-acetylglutamate
RTECS number
  • LZ9725000 S
UNII
  • 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) checkY
    Key: RFMMMVDNIPUKGG-UHFFFAOYSA-N checkY
  • 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)/t5-/m1/s1
    Key: RFMMMVDNIPUKGG-RXMQYKEDSA-N
  • 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)/t5-/m0/s1
    Key: RFMMMVDNIPUKGG-YFKPBYRVSA-N
  • CC(=O)NC(CCC(=O)O)C(=O)O
Properties
C7H11NO5
Molar mass 189.167 g·mol−1
Appearance White crystals
Density 1 g mL−1
Melting point 191 to 194 °C (376 to 381 °F; 464 to 467 K)
36 g L−1
Hazards
Lethal dose or concentration (LD, LC):
>7 g kg−1 (oral, rat)
Related compounds
Related alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

N-Acetylglutamic acid (also referred to as N-acetylglutamate, abbreviated NAG, chemical formula C7H11NO5)[2] is biosynthesized from glutamate and acetylornithine by ornithine acetyltransferase, and from glutamic acid and acetyl-CoA by the enzyme N-acetylglutamate synthase. The reverse reaction, hydrolysis of the acetyl group, is catalyzed by a specific hydrolase. It is the first intermediate involved in the biosynthesis of arginine in prokaryotes and simple eukaryotes and a regulator in the process known as the urea cycle that converts toxic ammonia to urea for excretion from the body in vertebrates.

  1. ^ "N-Acetyl-DL-glutamic acid - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification. Retrieved 25 June 2012.
  2. ^ Pubchem. "N-Acetyl L-glutamic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2018-06-03.