Details of Metabolite

General Information of MET (ID: META00561)
Name N-Acetylglutamine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S)-2-Acetamido-5-amino-5-oxopentanoic acid; (2S)-4-Carbamoyl-2-acetamidobutanoic acid; Aceglutamide; Acetylglutamine; L-N2-Acetyl-glutamine; L-N2-Acetylglutamine; N-Acetyl-L-glutamine; N-Acetylglutamine; N2-Acetyl-L-glutamine; N2-Acetylglutamine; NAcGln; N~2~-acetyl-L-glutamine
Source Endogenous;Yeast Metabolite;Food
Structure Type   Amino acids, peptides, and analogues  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
PubChem CID
182230
HMDB ID
HMDB0006029
Formula
C7H12N2O4
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
DrugBank ID
DB04167
ChEBI ID
21553
FooDB ID
FDB023808
ChemSpider ID
158492
Physicochemical Properties Molecular Weight 188.18 Topological Polar Surface Area 110
XlogP -1.4 Complexity 227
Heavy Atom Count 13 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Function
N-Acetylglutamine (NAcGln) is a modified amino acid (an acetylated analogue of glutamine) and is a metabolite present in normal human urine. The decomposition products of NAcGln 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. NAcGln is used for parenteral nutrition as a source of glutamine since glutamine is too unstable whereas NAcGln is very stable. In patients treated with aminoglycosides and/or glycopeptides, an elevation of NAcGln in urine suggests renal tubular injury. High amounts of N-acetylated amino acids (i.e. N-acetylglutamine) were detected in a 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.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Leukotriene-C4 hydrolase (GGT1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockdown (siRNA) of GGT1
                      Induced Change N-Acetylglutamine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Renal cell carcinoma [ICD-11: 2C90]
                      Details It is reported that knockdown of GGT1 leads to the increase of N-acetylglutamine levels compared with control group.
      Oxidoreductases (EC 1)
            L-2-hydroxyglutarate dehydrogenase (L2HGDH) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Mutation (Nonsense mutations or missense mutations) of L2hgdh
                      Induced Change N-Acetylglutamine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Melanoma [ICD-11: 2C30]
                      Details It is reported that mutation (nonsense mutations or missense mutations leading to KMT2D loss) of L2hgdh leads to the increase of N-acetylglutamine levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Knockout of TP53
                      Induced Change N-Acetylglutamine concentration: decrease (Log2 FC=0.59)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the decrease of N-acetylglutamine levels compared with control group.
References
1 Impairment of gamma-glutamyl transferase 1 activity in the metabolic pathogenesis of chromophobe renal cell carcinoma. Proc Natl Acad Sci U S A. 2018 Jul 3;115(27):E6274-E6282.
2 Enhancer Reprogramming Confers Dependence on Glycolysis and IGF Signaling in KMT2D Mutant Melanoma. Cell Rep. 2020 Oct 20;33(3):108293.
3 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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