Details of Metabolite

General Information of MET (ID: META00239)
Name Xanthine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1H-Purine-2,6-diol; 2,6(1,3)-Purinedion; 2,6-Dihydroxypurine; 2,6-Dioxo-1,2,3,6-tetrahydropurine; 2,6-Dioxopurine; 3,7-Dihydro-1H-purine-2,6-dione; 3,7-Dihydropurine-2,6-dione; 9H-Purine-2,6(1H,3H)-dione; 9H-Purine-2,6-(1H,3H)-dione; 9H-Purine-2,6-diol; Dioxopurine; Isoxanthine; Pseudoxanthine; Purine-2(3H),6(1H)-dione; Purine-2,6(1H,3H)-dione; Purine-2,6-diol; Xan; Xanthic oxide; Xanthin
Source Endogenous;Drug Metabolite;Escherichia Coli Metabolite;Yeast Metabolite;Food;Drug;Agricultural Chemicals;Toxins/Pollutant;Cosmetic;TCM Ingredients;Microbial
Structure Type   Purines and purine derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Imidazopyrimidines
Purines and purine derivatives
PubChem CID
1188
HMDB ID
HMDB0000292
Formula
C5H4N4O2
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=1188"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00385
DrugBank ID
DB02134
ChEBI ID
17712
FooDB ID
FDB001977
ChemSpider ID
1151
METLIN ID
82
Physicochemical Properties Molecular Weight 152.11 Topological Polar Surface Area 86.9
XlogP -0.7 Complexity 217
Heavy Atom Count 11 Rotatable Bond Count N.A.
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Function
Xanthine is a purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects (Dorland, 28th ed.). Xanthine is found to be associated with Lesch-Nyhan syndrome and xanthinuria type I, which are inborn errors 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 Xanthine 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 xanthine 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 Xanthine concentration: increase (FC = 4.17)
                      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 xanthine levels compared with control group.
            Selenocysteine lyase (SCLY) 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 Scly
                      Induced Change Xanthine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Scly leads to the decrease of xanthine 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 [4]
                      Introduced Variation Knockout of TP53
                      Induced Change Xanthine concentration: increase (Log2 FC=4.49)
                      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 xanthine levels compared with control group.
      Transferases (EC 2)
            Deacetylase sirtuin-5 (SIRT5) 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 Knockout of Sirt5
                      Induced Change Xanthine concentration: increase (FC = 1.38)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Sirt5 leads to the increase of xanthine 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 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 Combined Omics Reveals That Disruption of the Selenocysteine Lyase Gene Affects Amino Acid Pathways in Mice. Nutrients. 2019 Oct 26;11(11):2584.
4 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.
5 Metabolomics Based Identification of SIRT5 and Protein Kinase C Epsilon Regulated Pathways in Brain. Front Neurosci. 2018 Jan 30;12:32.

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