Details of Metabolite

General Information of MET (ID: META00339)
Name Xanthurenic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
4,8-Dihydroxy-2-quinolinecarboxylate; 4,8-Dihydroxy-2-quinolinecarboxylic acid; 4,8-Dihydroxy-quinaldate; 4,8-Dihydroxy-quinaldic acid; 4,8-Dihydroxyquinaldate; 4,8-Dihydroxyquinaldic acid; 4,8-Dihydroxyquinaldinate; 4,8-Dihydroxyquinaldinic acid; 4,8-Dihydroxyquinoline-2-carboxylate; 4,8-Dihydroxyquinoline-2-carboxylic acid; 4-Oxoxanthurenic acid; 8-Hydroxykynurenate; 8-Hydroxykynurenic acid; Gametocyte activating factor (gaf); Oxoxanthurenate; Xanthurate; Xanthurenate; Xanthuric acid
Source Endogenous;Yeast Metabolite;Food;TCM Ingredients;Microbial
Structure Type   Quinoline carboxylic acids  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Quinolines and derivatives
Quinoline carboxylic acids
PubChem CID
5699
HMDB ID
HMDB0000881
Formula
C10H7NO4
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
C02470
ChEBI ID
10072
FooDB ID
FDB022297
ChemSpider ID
5497
METLIN ID
5841
Physicochemical Properties Molecular Weight 205.17 Topological Polar Surface Area 86.6
XlogP 0.9 Complexity 336
Heavy Atom Count 15 Rotatable Bond Count 1
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Function
Xanthurenic acid, also known as xanthurenate or 8-hydroxykynurenic acid, is a member of the class of compounds known as quinoline carboxylic acids. Quinoline carboxylic acids are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Xanthurenic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Xanthurenic acid can be found primarily in blood, feces, and urine, as well as in human epidermis tissue. Within the cell, xanthurenic acid is primarily located in the membrane. Xanthurenic acid exists in all eukaryotes, ranging from yeast to humans. In humans, xanthurenic acid is involved in the tryptophan metabolism. Moreover, xanthurenic acid is found to be associated with citrullinemia type I, which is an inborn error of metabolism. Xanthurenic acid is a metabolite from tryptophan catabolism. It is a substrate of the enzyme methyltransferases (EC 2.1.1.-) in pathway tryptophan metabolism (KEGG).
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 Xanthurenic acid concentration: decrease (FC = 0.69)
                      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 xanthurenic acid levels compared with control group.
      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 [2]
                      Introduced Variation Knockdown (siRNA) of GGT1
                      Induced Change Xanthurenic acid 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 xanthurenic acid levels compared with control group.
      Interleukin (IL)
            Interleukin-10 (IL10) 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 IL10
                      Induced Change Xanthurenic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Crohn disease [ICD-11: DD70]
                      Details It is reported that knockout of IL10 leads to the increase of xanthurenic 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 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.
3 Nontargeted urinary metabolite profiling of a mouse model of Crohn&#39;s disease. J Proteome Res. 2009 Apr;8(4):2045-57.

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