General Information of MET (ID: META00307)
Name Hippuric acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(Benzoylamino)-acetate; (Benzoylamino)-acetic acid; 2-Benzamidoacetate; 2-Benzamidoacetic acid; Benzamidoacetate; Benzamidoacetic acid; Benzamidoessigsaeure; Benzoylaminoacetate; Benzoylaminoacetic acid; Benzoylaminoessigsaeure; Benzoylglycine; Hippate; Hippic acid; Hippurate; Hippursaeure; N-Benzoylglycinate; N-Benzoylglycine; Phenylcarbonylaminoacetate; Phenylcarbonylaminoacetic acid
Source Endogenous;Drug Metabolite;Food;Toxins/Pollutant;Cosmetic;TCM Ingredients;Styrene;Microbial; Herbal Ingredients In-Vivo Metabolism
Structure Type   Benzoic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Benzenoids
Benzene and substituted derivatives
Benzoic acids and derivatives
PubChem CID
464
HMDB ID
HMDB0000714
Formula
C9H9NO3
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
C01586
ChEBI ID
18089
FooDB ID
FDB001819
ChemSpider ID
451
METLIN ID
1301
Physicochemical Properties Molecular Weight 179.17 Topological Polar Surface Area 66.4
XlogP 0.3 Complexity 197
Heavy Atom Count 13 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
Hippuric acid is an acyl glycine formed from the conjugation of benzoic acid with glycine. 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. Hippuric acid is a normal component of urine and is typically increased with increased consumption of phenolic compounds (tea, wine, fruit juices). These phenols are converted into benzoic acid which is then converted into hippuric acid and excreted in the urine. Hippuric acid is the most frequently used biomarker in the biological monitoring of occupational exposure to toluene. This product of solvent biotransformation may be also found in the urine of individuals who have not been exposed to the solvent. A smaller fraction of the absorbed toluene is oxidized into aromatic compounds including ortho-cresol, which is not found in the urine of nonexposed individuals in a significant amount. The concentration of hippuric acid in the urine of individuals exposed to a low toluene concentration does not differ from that of individuals not exposed to the solvent. This has led to the conclusion that hippuric acid should not be utilized in the biological monitoring of occupational exposure to low levels of toluene in the air. Protein-bound organic acids such as hippuric acid are markedly accumulated in uremic plasma and produce defective protein binding of drugs. Hippuric acid has been identified as a uremic toxin according to the European Uremic Toxin Working Group. Hippuric acid is also found to be associated with phenylketonuria, propionic acidemia, and tyrosinemia I, which are inborn errors of metabolism. Hippuric acid is an endogenous phenolic acid metabolite detected after the consumption of whole grain.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Apolipoprotein (Apo)
            Apolipoprotein A-II (APOA2) 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 Mutation (-265T >C(rs5082)) of APOA2
                      Induced Change Hippuric acid concentration: decrease (FC = 0.47)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that mutation (-265T >C(rs5082)) of APOA2 leads to the decrease of hippuric acid levels compared with control group.
      Hydrolases (EC 3)
            GTPase KRas (KRAS) 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 Overexpression of KRAS
                      Induced Change Hippuric acid concentration: increase (FC = 1.79)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Lung cancer [ICD-11: 2C25]
                      Details It is reported that overexpression of KRAS leads to the increase of hippuric acid levels compared with control group.
References
1 Epigenomics and metabolomics reveal the mechanism of the APOA2-saturated fat intake interaction affecting obesity. Am J Clin Nutr. 2018 Jul 1;108(1):188-200.
2 Capturing the metabolomic diversity of KRAS mutants in non-small-cell lung cancer cells. Oncotarget. 2014 Jul 15;5(13):4722-31.

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