Details of Metabolite

General Information of MET (ID: META00242)
Name Xanthosine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
3,9-Dihydro-9-D-ribofuranosyl-1H-purine-2,6-dione; 3,9-Dihydro-9-b-D-ribofuranosyl-1H-purine-2,6-dione; 3,9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2,6-dione; 3,9-Dihydro-9-delta-ribofuranosyl-1H-purine-2,6-dione; 9 beta-D-Ribofuranosylxanthine; 9-D-Ribofuranosylxanthine; 9-beta-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione; 9-beta-D-Ribofuranosylxanthine; 9-beta-delta-Ribofuranosylxanthine; 9-delta-Ribofuranosylxanthine; Xanthine 9-beta-D-ribofuranoside; Xanthine riboside
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Microbial
Structure Type   Purine nucleosides  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
Purine nucleosides
PubChem CID
64959
HMDB ID
HMDB0000299
Formula
C10H12N4O6
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
C01762
ChEBI ID
18107
FooDB ID
FDB001604
ChemSpider ID
58484
METLIN ID
3408
Physicochemical Properties Molecular Weight 284.23 Topological Polar Surface Area 146
XlogP -2.4 Complexity 434
Heavy Atom Count 20 Rotatable Bond Count 2
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 7
Function
Biological Source: Xanthosine is produced by guanine-free mutants of bacteria e.g. Bacillus subtilis, Aerobacter aerogenes. Also reported from seeds of Trifolium alexandrinum Physical Description: Prismatic cryst. (H2O) (Chemnetbase) The deamination product of guanosine. Xanthosine monophosphate is an intermediate in purine metabolism, formed from IMP, and forming GMP. Xanthylic acid can be used in quantitative measurements of the Inosine monophosphate dehydrogenase enzyme activities in purine metabolism, as recommended to ensure optimal thiopurine therapy for children with acute lymphoblastic leukaemia (ALL).
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 Xanthosine 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 xanthosine levels compared with control group.
            Sulfatase sulf-1 (SULF1) 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 (shRNA) of SULF1
                      Induced Change Xanthosine concentration: increase (FC = 4.12)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of xanthosine 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 [3]
                      Introduced Variation Knockout of Cth
                      Induced Change Xanthosine concentration: increase (FC = 3.08)
                      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 xanthosine 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 Xanthosine concentration: increase (Log2 FC=5.92)
                      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 xanthosine 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 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
3 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.
4 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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