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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:44:40 UTC
HMDB IDHMDB0000299
Secondary Accession Numbers
  • HMDB00299
Metabolite Identification
Common NameXanthosine
DescriptionXanthosine, also known as xanthine riboside, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Xanthosine is a nucleoside derived from xanthine and ribose. Xanthosine exists in all living species, ranging from bacteria to plants to humans. In plants xanthosine is the biosynthetic precursor to 7-methylxanthosine which is produced by the action of the enzyme known as 7-methylxanthosine synthase. 7-Methylxanthosine in turn is the precursor to theobromine (the active alkaloid in chocolate), which in turn is the precursor to caffeine, the active alkaloid in coffee and tea. Within humans, xanthosine participates in a number of enzymatic reactions. In particular, xanthosine can be biosynthesized from xanthylic acid; which is catalyzed by the enzyme cytosolic purine 5'-nucleotidase. In addition, xanthosine can be converted into xanthine and ribose 1-phosphate; which is mediated by the enzyme purine nucleoside phosphorylase. Xanthosine monophosphate (XMP) is an intermediate in purine metabolism, formed from IMP (inosine monophosphate).
Structure
Data?1582752121
Synonyms
ValueSource
9-beta-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dioneChEBI
9-beta-D-RibofuranosylxanthineChEBI
Xanthine 9-beta-D-ribofuranosideChEBI
Xanthine ribosideChEBI
9-b-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dioneGenerator
9-Β-D-ribofuranosyl-3,9-dihydro-1H-purine-2,6-dioneGenerator
9-b-D-RibofuranosylxanthineGenerator
9-Β-D-ribofuranosylxanthineGenerator
Xanthine 9-b-D-ribofuranosideGenerator
Xanthine 9-β-D-ribofuranosideGenerator
3,9-Dihydro-9-b-D-ribofuranosyl-1H-purine-2,6-dioneHMDB
3,9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2,6-dioneHMDB
3,9-Dihydro-9-D-ribofuranosyl-1H-purine-2,6-dioneHMDB
3,9-Dihydro-9-delta-ribofuranosyl-1H-purine-2,6-dioneHMDB
9-beta-delta-RibofuranosylxanthineHMDB
9-D-RibofuranosylxanthineHMDB
9-delta-RibofuranosylxanthineHMDB
9 beta-D-RibofuranosylxanthineHMDB
Chemical FormulaC10H12N4O6
Average Molecular Weight284.2255
Monoisotopic Molecular Weight284.075684136
IUPAC Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol
Traditional Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purine-2,6-diol
CAS Registry Number146-80-5
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O
InChI Identifier
InChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1
InChI KeyUBORTCNDUKBEOP-UUOKFMHZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Pentose monosaccharide
  • Purine
  • Imidazopyrimidine
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azole
  • Vinylogous amide
  • Lactam
  • Urea
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg154.030932474
[M-H]-Baker161.36330932474
[M+H]+Astarita_pos157.730932474
[M+H]+Baker166.4930932474
[M-H]-Not Available159.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00000156
[M+H]+Not Available163.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00000156
Predicted Molecular Properties
PropertyValueSource
Water Solubility27.8 g/LALOGPS
logP10(-1.6) g/LALOGPS
logP10(-1.2) g/LChemAxon
logS10(-1) g/LALOGPS
pKa (Strongest Acidic)11.33ChemAxon
pKa (Strongest Basic)0.078ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.98 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.4 m³·mol⁻¹ChemAxon
Polarizability25.55 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.36331661259
DarkChem[M-H]-159.48331661259
AllCCS[M+H]+163.04632859911
AllCCS[M-H]-160.53132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
XanthosineOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O3692.7Standard polar33892256
XanthosineOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O1866.2Standard non polar33892256
XanthosineOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O2650.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Xanthosine,1TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O)[C@@H]1O2938.4Semi standard non polar33892256
Xanthosine,1TMS,isomer #2C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(O)N=C(O)N=C212942.9Semi standard non polar33892256
Xanthosine,1TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@@H]1O2927.6Semi standard non polar33892256
Xanthosine,1TMS,isomer #4C[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=N12840.6Semi standard non polar33892256
Xanthosine,1TMS,isomer #5C[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O2802.6Semi standard non polar33892256
Xanthosine,2TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O)N=C32)[C@H](O)[C@@H]1O2777.1Semi standard non polar33892256
Xanthosine,2TMS,isomer #10C[Si](C)(C)OC1=NC(O[Si](C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=N12707.5Semi standard non polar33892256
Xanthosine,2TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C)N=C32)[C@H](O)[C@@H]1O2802.9Semi standard non polar33892256
Xanthosine,2TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O2917.7Semi standard non polar33892256
Xanthosine,2TMS,isomer #4C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C2899.7Semi standard non polar33892256
Xanthosine,2TMS,isomer #5C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@@H]1O[Si](C)(C)C2902.2Semi standard non polar33892256
Xanthosine,2TMS,isomer #6C[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C2783.0Semi standard non polar33892256
Xanthosine,2TMS,isomer #7C[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O[Si](C)(C)C)C2=N12810.1Semi standard non polar33892256
Xanthosine,2TMS,isomer #8C[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O2771.3Semi standard non polar33892256
Xanthosine,2TMS,isomer #9C[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]3O)C2=N12793.7Semi standard non polar33892256
Xanthosine,3TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O[Si](C)(C)C)N=C32)[C@H](O)[C@@H]1O2687.0Semi standard non polar33892256
Xanthosine,3TMS,isomer #10C[Si](C)(C)OC1=NC(O[Si](C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]3O)C2=N12703.5Semi standard non polar33892256
Xanthosine,3TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O2701.4Semi standard non polar33892256
Xanthosine,3TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C2689.3Semi standard non polar33892256
Xanthosine,3TMS,isomer #4C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O2749.9Semi standard non polar33892256
Xanthosine,3TMS,isomer #5C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C2737.2Semi standard non polar33892256
Xanthosine,3TMS,isomer #6C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2853.1Semi standard non polar33892256
Xanthosine,3TMS,isomer #7C[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C2694.2Semi standard non polar33892256
Xanthosine,3TMS,isomer #8C[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C2=N12736.2Semi standard non polar33892256
Xanthosine,3TMS,isomer #9C[Si](C)(C)OC1=NC(O[Si](C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O[Si](C)(C)C)C2=N12699.1Semi standard non polar33892256
Xanthosine,4TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O[Si](C)(C)C)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O2709.0Semi standard non polar33892256
Xanthosine,4TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O[Si](C)(C)C)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C2700.1Semi standard non polar33892256
Xanthosine,4TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2662.3Semi standard non polar33892256
Xanthosine,4TMS,isomer #4C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2717.8Semi standard non polar33892256
Xanthosine,4TMS,isomer #5C[Si](C)(C)OC1=NC(O[Si](C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C2=N12710.5Semi standard non polar33892256
Xanthosine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O[Si](C)(C)C)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2737.5Semi standard non polar33892256
Xanthosine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O)[C@@H]1O3210.5Semi standard non polar33892256
Xanthosine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(O)N=C(O)N=C213215.6Semi standard non polar33892256
Xanthosine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@@H]1O3199.1Semi standard non polar33892256
Xanthosine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=N13070.9Semi standard non polar33892256
Xanthosine,1TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O3039.7Semi standard non polar33892256
Xanthosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=C(O)N=C32)[C@H](O)[C@@H]1O3238.3Semi standard non polar33892256
Xanthosine,2TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC1=NC(O[Si](C)(C)C(C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=N13134.4Semi standard non polar33892256
Xanthosine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O)[C@@H]1O3277.9Semi standard non polar33892256
Xanthosine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3418.3Semi standard non polar33892256
Xanthosine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3415.3Semi standard non polar33892256
Xanthosine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@@H]1O[Si](C)(C)C(C)(C)C3403.1Semi standard non polar33892256
Xanthosine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C3229.9Semi standard non polar33892256
Xanthosine,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)C2=N13271.3Semi standard non polar33892256
Xanthosine,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O3222.8Semi standard non polar33892256
Xanthosine,2TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)C2=N13266.3Semi standard non polar33892256
Xanthosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O)[C@@H]1O3330.7Semi standard non polar33892256
Xanthosine,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC1=NC(O[Si](C)(C)C(C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)C2=N13338.4Semi standard non polar33892256
Xanthosine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=C(O)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3355.2Semi standard non polar33892256
Xanthosine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=C(O)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3351.7Semi standard non polar33892256
Xanthosine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3416.6Semi standard non polar33892256
Xanthosine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3410.8Semi standard non polar33892256
Xanthosine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3523.2Semi standard non polar33892256
Xanthosine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C3345.5Semi standard non polar33892256
Xanthosine,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)C2=N13407.7Semi standard non polar33892256
Xanthosine,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC1=NC(O[Si](C)(C)C(C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)C2=N13334.0Semi standard non polar33892256
Xanthosine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3502.4Semi standard non polar33892256
Xanthosine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3503.4Semi standard non polar33892256
Xanthosine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=C(O)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3481.9Semi standard non polar33892256
Xanthosine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3535.2Semi standard non polar33892256
Xanthosine,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=NC(O[Si](C)(C)C(C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)C2=N13492.9Semi standard non polar33892256
Xanthosine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3682.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Xanthosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0032-0963000000-08e48347b76242e521e62014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Xanthosine GC-EI-TOF (Non-derivatized)splash10-0032-0963000000-08e48347b76242e521e62017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9250000000-9694fd3e1c7370e278662017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (5 TMS) - 70eV, Positivesplash10-0059-2110049000-cbeec0d3159947f31d5f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthosine GC-MS (TMS_3_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0udi-0900000000-e3e76f5bf26f34680c352012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0udi-7900000000-6e1f70509da5adf996782012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4r-9500000000-3cce63949eec45fa92042012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0udi-0910000000-b2c7e01e9105bba310aa2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0udi-0910000000-e6e1d21c0d22b3ad28212012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine LC-ESI-QTOF , negative-QTOFsplash10-0udi-0910000000-b2c7e01e9105bba310aa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine LC-ESI-QTOF , negative-QTOFsplash10-0udi-0910000000-e6e1d21c0d22b3ad28212017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine 40V, Positive-QTOFsplash10-0uk9-8900000000-b0f93d77cf447ada9ed92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine 20V, Positive-QTOFsplash10-0udi-1900000000-19c92745c311f6435fd32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine 35V, Positive-QTOFsplash10-0udi-2910000000-6f97748a645ffb972e672021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine 0V, Positive-QTOFsplash10-03di-0900000000-a999e0e022115ec9ec7a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine 10V, Positive-QTOFsplash10-0udi-0910000000-63959f162289e268a6202021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine 20V, Positive-QTOFsplash10-0zg0-8900000000-f8aa72afbf821cfb2cf22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine 10V, Positive-QTOFsplash10-0udi-4900000000-943b0d3fbe3cd8345d542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine 40V, Positive-QTOFsplash10-06rl-9400000000-3072bed88bbdca66de692021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine 35V, Negative-QTOFsplash10-0udi-0900000000-f3b10c4bf03522fbd1ff2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine 10V, Negative-QTOFsplash10-0udi-0940000000-f59c82b81d81cd9c6b682021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine 30V, Negative-QTOFsplash10-0udi-0900000000-e0cf07456bb1d35aec562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthosine 20V, Negative-QTOFsplash10-0udi-0900000000-6189db27589e05c3f0392021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthosine 10V, Positive-QTOFsplash10-0udi-0940000000-2394018b58d040767e062016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthosine 20V, Positive-QTOFsplash10-0udi-0900000000-fec1dd4fe1f5f7e564822016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthosine 40V, Positive-QTOFsplash10-0f79-1900000000-850759ea222062877fa92016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthosine 10V, Negative-QTOFsplash10-0f8c-1590000000-4fdccf755ee2b8b75ac62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthosine 20V, Negative-QTOFsplash10-0f6x-6910000000-308e886a8ecec5d8cd092016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthosine 40V, Negative-QTOFsplash10-0006-9500000000-af861bef2f6b2f10296c2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.08 +/- 0.30 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0842 +/- 0.0451 uMAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.59 +/- 0.36 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.340 +/- 0.221 uMAdult (>18 years old)Both
Uremia
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Metastatic melanoma
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
UrineDetected and Quantified0.99 umol/mmol creatinineAdult (>18 years old)BothBreast tumour details
Associated Disorders and Diseases
Disease References
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Metastatic melanoma
  1. Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001604
KNApSAcK IDC00007222
Chemspider ID58484
KEGG Compound IDC01762
BioCyc IDXANTHOSINE
BiGG ID38352
Wikipedia LinkXanthosine
METLIN ID3408
PubChem Compound64959
PDB IDNot Available
ChEBI ID18107
Food Biomarker OntologyNot Available
VMH IDXTSN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceEnei, Hitoshi; Sato, Katsuaki; Hirose, Yoshio. Xanthosine production by fermentation. Jpn. Kokai Tokkyo Koho (1975), 3 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Marti R, Nishigaki Y, Hirano M: Elevated plasma deoxyuridine in patients with thymidine phosphorylase deficiency. Biochem Biophys Res Commun. 2003 Mar 28;303(1):14-8. [PubMed:12646159 ]
  2. Dudley E, Lemiere F, Van Dongen W, Tuytten R, El-Sharkawi S, Brenton AG, Esmans EL, Newton RP: Analysis of urinary nucleosides. IV. Identification of urinary purine nucleosides by liquid chromatography/electrospray mass spectrometry. Rapid Commun Mass Spectrom. 2004;18(22):2730-8. [PubMed:15499664 ]
  3. Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. [PubMed:9129323 ]
  4. Khalil PN, Erb N, Khalil MN, Escherich G, Janka-Schaub GE: Validation and application of a high-performance liquid chromatographic-based assay for determination of the inosine 5'-monophosphate dehydrogenase activity in erythrocytes. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Sep 14;842(1):1-7. Epub 2006 May 24. [PubMed:16725387 ]
  5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
Reactions
Xanthylic acid + Water → Xanthosine + Phosphatedetails
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Molecular weight:
68803.055
Reactions
Xanthylic acid + Water → Xanthosine + Phosphatedetails
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Molecular weight:
41020.145
Reactions
Xanthylic acid + Water → Xanthosine + Phosphatedetails
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
Reactions
Xanthylic acid + Water → Xanthosine + Phosphatedetails
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
Reactions
Xanthylic acid + Water → Xanthosine + Phosphatedetails
General function:
Involved in hydrolase activity
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Molecular weight:
16833.23
General function:
Involved in magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91
Reactions
Xanthylic acid + Water → Xanthosine + Phosphatedetails
General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
P49902
Molecular weight:
64969.2
Reactions
Xanthylic acid + Water → Xanthosine + Phosphatedetails
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P00491
Molecular weight:
32117.69
Reactions
Xanthosine + Phosphate → Xanthine + Ribose 1-phosphatedetails