Details of Metabolite

General Information of MET (ID: META00327)
Name Phenylacetylglycine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
((Phenylacetyl)amino)acetic acid; N-(Phenylacetyl)-glycine; N-(Phenylacetyl)glycine; N-Phenacetylglycine; N-Phenylacetylglycine; PAA; PAG; Phenacetate; Phenacetic acid; Phenaceturate; Phenaceturic acid; Phenacetylglycine; Phenylacetyl glycine; Phenylacetylglycine; [(Phenylacetyl)amino]acetate; [(Phenylacetyl)amino]acetic acid
Source Endogenous;Yeast Metabolite;Food;Microbial
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
68144
HMDB ID
HMDB0000821
Formula
C10H11NO3
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C05598
ChEBI ID
27480
FooDB ID
FDB022266
ChemSpider ID
61452
METLIN ID
4237
Physicochemical Properties Molecular Weight 193.2 Topological Polar Surface Area 66.4
XlogP 0.7 Complexity 209
Heavy Atom Count 14 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
Phenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Phenylacetylglycine or PAG is a glycine conjugate of phenylacetic acid. Phenylacetic acid may arise from exposure to styrene (plastic) or through the consumption of fruits and vegetables. Phenylacetic acid is used in some perfumes, possessing a honey-like odour in low concentrations, and is also used in penicillin G production. PAG is a putative biomarker of phospholipidosis. Urinary PAG is elevated in animals exhibiting abnormal phospholipid accumulation in many tissues and may thus be useful as a surrogate biomarker for phospholipidosis. The presence of phenylacetylglycine in urine has been confirmed for dogs, rats and mice. However, the presence of this compound in human urine is controversial. GC-MS studies have not found this compound while NMR studies claimed to have identified it. It appears that phenylacetylglycine may sometimes be mistaken for phenylacetylglutamine via NMR.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      High mobility group N (HMGN)
            Nucleosome-binding protein 45 (NBP-45) 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 Knockout of Hmgn5
                      Induced Change Phenylacetylglycine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Hmgn5 leads to the decrease of phenylacetylglycine levels compared with control group.
      Lyases (EC 4)
            Cystathionine gamma-lyase (CTH) 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 Knockout of Cth
                      Induced Change Phenylacetylglycine concentration: increase (FC = 4.63)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Organic acid disorderss [ICD-11: 5C50]
                      Details It is reported that knockout of Cth leads to the increase of phenylacetylglycine 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 Phenylacetylglycine concentration: increase (Log2 FC=1.01)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of phenylacetylglycine levels compared with control group.
References
1 Metabolomics reveals a role for the chromatin-binding protein HMGN5 in glutathione metabolism. PLoS One. 2014 Jan 2;9(1):e84583.
2 Hydrogen Sulfide Is a Regulator of Hemoglobin Oxygen-Carrying Capacity via Controlling 2,3-BPG Production in Erythrocytes. Oxid Med Cell Longev. 2021 Feb 13;2021:8877691.
3 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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