Details of Metabolite

General Information of MET (ID: META00181)
Name Hypoxanthine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1,7-Dihydro-6H-purin-6-one; 1,7-Dihydro-6H-purine-6-one; 1H,7H-Hypoxanthine; 3H-Purin-6-ol; 4-Hydroxy-1H-purine; 6(1H)-Purinone; 6-Hydroxy-1H-purine; 6-Hydroxypurine; 6-Oxopurine; 7H-Purin-6-ol; 9H-Purin-6(1H)-one; 9H-Purin-6-ol; Hyp; Hypoxanthine enol; Purin-6(1H)-one; Purin-6(3H)-one; Purin-6-ol; Purine-6-ol; Sarcine; Sarkin; Sarkine
Source Aromatic heteropolycyclic compounds
Structure Type   Purines and purine derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Imidazopyrimidines
Purines and purine derivatives
PubChem CID
790
HMDB ID
HMDB0000157
Formula
C5H4N4O
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=790"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00262
DrugBank ID
DB04076
ChEBI ID
17368
FooDB ID
FDB003949
ChemSpider ID
768
METLIN ID
83
Physicochemical Properties Molecular Weight 136.11 Topological Polar Surface Area 70.1
XlogP -1.1 Complexity 190
Heavy Atom Count 10 Rotatable Bond Count N.A.
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Function
Hypoxanthine is a naturally occurring purine derivative and a reaction intermediate in the metabolism of adenosine and in the formation of nucleic acids by the salvage pathway. Hypoxanthine is also a spontaneous deamination product of adenine. Lesch-Nyhan disease, an inborn error of metabolism, is caused by deficiency of the purine salvage enzyme hypoxanthine-guanine phosphoribosyltransferase (OMIN 308000). Hypoxanthine is also found to be associated with xanthinuria type 1, which is an inborn error of metabolism. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group.
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 Hypoxanthine concentration: increase (FC = 1.56)
                      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 increase of hypoxanthine levels compared with control group.
      Hydrolases (EC 3)
            Adenosine deaminase 2 (ADA2) 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 ADA2
                      Induced Change Hypoxanthine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockdown of ADA2 leads to the increase of hypoxanthine levels compared with control group.
            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 [3]
                      Introduced Variation Knockdown (siRNA) of GGT1
                      Induced Change Hypoxanthine 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 hypoxanthine levels compared with control group.
      Nitrogen permease regulator (NPR)
            Natriuretic peptide receptor B (NPR2) 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 Deletion of NPR2
                      Induced Change Hypoxanthine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that deletion of NPR2 leads to the increase of hypoxanthine 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 [5]
                      Introduced Variation Knockout of TP53
                      Induced Change Hypoxanthine concentration: increase (Log2 FC=8.31)
                      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 hypoxanthine 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 Cellular sensing of extracellular purine nucleosides triggers an innate IFN- response. Sci Adv. 2020 Jul 22;6(30):eaba3688.
3 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.
4 Npr2 inhibits TORC1 to prevent inappropriate utilization of glutamine for biosynthesis of nitrogen-containing metabolites. Sci Signal. 2014 Dec 16;7(356):ra120.
5 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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