FComEx: N-Acetylglutamine (PC000966)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:39 UTC

Update date

2017-01-19 02:36:43 UTC

FoodComEx ID

PC000966

FoodDB Record

FDB023808

Chemical Information

Name

N-Acetylglutamine

Description

N-Acetylglutamine (GIcNAc) is a modified amino acid (an acetylated analogue of glutamine), a metabolite present in normal human urine. The decomposition products of GIcNAc 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. GIcNAc is used for parenteral nutrition as a source of glutamine, since glutamine is too unstable, but GIcNAc is very stable. In patients treated with aminoglycosides and/or glycopeptides, elevation GIcNAc in urine suggests renal tubular injury. High amounts of N-acetylated amino acids (i.e.: N-Acetylglutamine) were detected 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) [HMDB]

CAS Number

2490-97-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Aceglutamid	hmdb
Aceglutamide	hmdb
Acetylglutamine	hmdb
alpha-n-acetyl-l-glutamine	hmdb
L-2-Acetamidoglutaramic acid	hmdb
L-N2-acetyl-Glutamine	hmdb
N-acetyl-l-glutamine	hmdb
N2-Acetyl-L-glutamine	hmdb
N2-acetylglutamine	hmdb

Chemical Formula

C7H12N2O4

IUPAC name

4-carbamoyl-2-acetamidobutanoic acid

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)

InChI Key

KSMRODHGGIIXDV-UHFFFAOYSA-N

Isomeric SMILES

CC(=O)NC(CCC(N)=O)C(O)=O

Average Molecular Weight

188.1812

Monoisotopic Molecular Weight

188.079706882

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents