Details of Metabolite

General Information of MET (ID: META00452)
Name 4-Aminohippuric acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
4 Aminohippuric acid; 4-Aminohippate; 4-Aminohippic acid; 4-Aminohippurate; 4-Aminohippuric acid; Aminohippate; Aminohippic acid; Aminohippurate; Aminohippurate sodium; Aminohippuric acid; Chlorphentermine; N-(4-Aminobenzoyl)glycine; N-(Para-aminobenzoyl)glycine; N-(p-Aminobenzoyl)aminoacetate; N-(p-Aminobenzoyl)aminoacetic acid; N-(p-Aminobenzoyl)glycine; Nefrotest; Nephrotest; PAH; Paha; Para aminohippuric acid; Para-aminohippate; Para-aminohippic acid; Para-aminohippurate; Para-aminohippurate, sodium; Para-aminohippuric acid; Paraaminohippate; Paraaminohippic acid; Paraaminohippuric acid; Sodium para aminohippurate; Sodium para-aminohippurate; Sodium, aminohippurate; p Aminohippurate; p Aminohippuric acid; p-Aminohippate; p-Aminohippic acid; p-Aminohippurate; p-Aminohippuric acid
Source Endogenous;Food;Drug
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
2148
HMDB ID
HMDB0001867
Formula
C9H10N2O3
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
D06890
DrugBank ID
DB00345
ChEBI ID
104011
FooDB ID
FDB022720
ChemSpider ID
2063
METLIN ID
6359
Physicochemical Properties Molecular Weight 194.19 Topological Polar Surface Area 92.4
XlogP -0.9 Complexity 222
Heavy Atom Count 14 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Function
4-Aminohippuric acid 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. Renal proximal tubules secrete various organic anions, including drugs and p-aminohippurate (PAH). Uptake of PAH from blood into tubule cells occurs by exchange with intracellular alpha-ketoglutarate and is mediated by the organic anion transporter 1. PAH exit into tubule lumen is species specific and may involve ATP-independent and -dependent transporters. Enhanced secretion of p-aminohippuric acid occurs in Fanconi's syndrome (FS). FS is associated with numerous varieties of inherited and acquired conditions; FS is characterized by a generalized transport defect in the proximal tubules, leading to renal losses of glucose, phosphate, calcium, uric acid, amino acids, bicarbonates, and other organic compounds.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      ATP-binding cassette transporter (ABCT)
            ATP-binding cassette A8 (ABCA8) 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 Overexpression of ABCA8
                      Induced Change 4-Aminohippuric acid concentration: increase (FC = 1.1)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of ABCA8 leads to the increase of 4-aminohippuric acid levels compared with control group.
      Organic ion transporter (OIT)
            Organic anion transporter 1 (OAT1) Click to Show/Hide the Full List of Regulating Pair(s):   7 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Mutation (F438Y) of SLC22A6
                      Induced Change 4-Aminohippuric acid concentration: decrease (FC = 0.30)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that mutation (F438Y) of SLC22A6 leads to the decrease of 4-aminohippuric acid levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Mutation (K431R) of SLC22A6
                      Induced Change 4-Aminohippuric acid concentration: decrease (FC = 0.30)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that mutation (K431R) of SLC22A6 leads to the decrease of 4-aminohippuric acid levels compared with control group.
               Regulating Pair (3) Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Inhibition (Furosemide) of SLC22A6
                      Induced Change 4-Aminohippuric acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that inhibition of SLC22A6 leads to the decrease of 4-aminohippuric acid levels compared with control group.
               Regulating Pair (4) Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Inhibition (Indomethacin) of SLC22A6
                      Induced Change 4-Aminohippuric acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that inhibition of SLC22A6 leads to the decrease of 4-aminohippuric acid levels compared with control group.
               Regulating Pair (5) Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Inhibition (Probenecid) of SLC22A6
                      Induced Change 4-Aminohippuric acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that inhibition of SLC22A6 leads to the decrease of 4-aminohippuric acid levels compared with control group.
               Regulating Pair (6) Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Inhibition (Steviol) of SLC22A6
                      Induced Change 4-Aminohippuric acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that inhibition of SLC22A6 leads to the decrease of 4-aminohippuric acid levels compared with control group.
               Regulating Pair (7) Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Inhibition (Unlabeled Para-aminohippurate (PAH)) of SLC22A6
                      Induced Change 4-Aminohippuric acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that inhibition of SLC22A6 leads to the decrease of 4-aminohippuric acid levels compared with control group.
            Solute carrier family 22 member 13 (SLC22A13) 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 [4]
                      Introduced Variation Overexpression of SLC22A13
                      Induced Change 4-Aminohippuric acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC22A13 leads to the increase of 4-aminohippuric acid levels compared with control group.
            Solute carrier family 22 member 7 (SLC22A7) 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 [5]
                      Introduced Variation Overexpression of SLC22A7
                      Induced Change 4-Aminohippuric acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC22A7 leads to the increase of 4-aminohippuric acid levels compared with control group.
      Sodium/anion cotransporter (SAC)
            Sodium-dependent phosphate transport 4 (SLC17A3) 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 [6]
                      Introduced Variation Overexpression of SLC17A3
                      Induced Change 4-Aminohippuric acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC17A3 leads to the increase of 4-aminohippuric acid levels compared with control group.
References
1 ATP-Binding Cassette Transporter A Subfamily 8 Is a Sinusoidal Efflux Transporter for Cholesterol and Taurocholate in Mouse and Human Liver. Mol Pharm. 2018 Feb 5;15(2):343-355.
2 A three-dimensional model of human organic anion transporter 1: aromatic amino acids required for substrate transport. J Biol Chem. 2006 Dec 8;281(49):38071-9.
3 Transport of the natural sweetener stevioside and its aglycone steviol by human organic anion transporter (hOAT1; SLC22A6) and hOAT3 (SLC22A8). J Pharmacol Exp Ther. 2005 May;313(2):621-8.
4 Intestinal dehydroascorbic acid (DHA) transport mediated by the facilitative sugar transporters, GLUT2 and GLUT8. J Biol Chem. 2013 Mar 29;288(13):9092-101.
5 Interaction of human organic anion transporters 2 and 4 with organic anion transport inhibitors. J Pharmacol Exp Ther. 2002 Jun;301(3):797-802.
6 Human sodium phosphate transporter 4 (hNPT4/SLC17A3) as a common renal secretory pathway for drugs and urate. J Biol Chem. 2010 Nov 5;285(45):35123-32.

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