Survey with prize
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:01 UTC
Secondary Accession Numbers
  • HMDB00293
Metabolite Identification
Common NameXanthosine 5-triphosphate
DescriptionXanthosine 5-triphosphate (XTP) is a Guanosine triphosphate (GTP) analogue. The base of XTP, xanthine, bears a keto group instead of an amino group at C2 of the purine rings. XTP can substitute for GTP in supporting receptor-mediated adenylyl cyclase activation. XTP competitively inhibits the binding of GTP to the guanine nucleotide-binding site of retinal G-protein, transducin (TD). These suggests that GTP, ITP, and XTP are differential signal sorters and signal amplifiers at the G-protein level. G-proteins mediate signal transfer from receptors to effector systems. (PMID: 9337071 ). Xanthosine 5-triphosphate is an intermediate of the Purine metabolism pathway, a substrate of the enzymes dinucleoside tetraphosphatase (EC and nucleoside-triphosphate pyrophosphatase (EC (KEGG).
Triphopsphoric acid 1-xanthosin-5'-yl esterChEBI
Xanthosine 5'-triphosphateChEBI
Xanthosine triphosphateChEBI
Triphopsphate 1-xanthosin-5'-yl esterGenerator
Triphopsphic acid 1-xanthosin-5'-yl esterGenerator
Xanthosine 5'-triphosphoric acidGenerator
Xanthosine triphosphoric acidGenerator
Xanthosine 5-triphosphoric acidGenerator
Xanthosine mono(tetrahydrogen triphosphate)HMDB
Xanthosine 5'-triphosphate 2Sodium saltHMDB
Chemical FormulaC10H15N4O15P3
Average Molecular Weight524.1652
Monoisotopic Molecular Weight523.974675366
IUPAC Name({[({[(2R,3S,4R,5R)-5-(2,6-dihydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional Namexanthosine 5-triphosphate
CAS Registry Number6253-56-1
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside triphosphates
Alternative Parents
  • Purine ribonucleoside triphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Xanthine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Alkaloid or derivatives
  • Monoalkyl phosphate
  • Hydroxypyrimidine
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors


Biological location:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility4.04 g/LALOGPS
pKa (Strongest Acidic)0.96ChemAxon
pKa (Strongest Basic)0.016ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area293.57 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity95.02 m³·mol⁻¹ChemAxon
Polarizability39.11 ųChemAxon
Number of Rings3ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6s-8956230000-c953b27fc23e558f8bc3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fmi-3120921000-30ff3765201db0daec17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0911220000-7c9e13bd8e928a2e5785Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-840c07c15dbc79ad0f2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-bd6b424553d786306979Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kor-1830690000-f39abfd999faa04d6195Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kbf-9620000000-5b4fb80ecb79a0415518Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9710000000-ed7594e6df7e2139120bSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue Locations
  • Prostate
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021932
KNApSAcK IDNot Available
Chemspider ID388429
KEGG Compound IDC00700
BioCyc IDNot Available
BiGG ID35735
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439296
PDB IDNot Available
ChEBI ID10049
Food Biomarker OntologyNot Available
MarkerDB ID
Synthesis Referenceanachkov I; Pan J Y; Wessling-Resnick M; Wright G E Synthesis and effect of nonhydrolyzable xanthosine triphosphate derivatives on prenylation of Rab5D136N. Molecular pharmacology (1997), 51(1), 47-51.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Klinker JF, Seifert R: Functionally nonequivalent interactions of guanosine 5'-triphosphate, inosine 5'-triphosphate, and xanthosine 5'-triphosphate with the retinal G-protein, transducin, and with Gi-proteins in HL-60 leukemia cell membranes. Biochem Pharmacol. 1997 Sep 1;54(5):551-62. [PubMed:9337071 ]


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:
Uniprot ID:
Molecular weight:
Xanthosine 5-triphosphate + Water → Xanthylic acid + Pyrophosphatedetails
General function:
Involved in hydrolase activity
Specific function:
Asymmetrically hydrolyzes Ap4A to yield AMP and ATP. Plays a major role in maintaining homeostasis.
Gene Name:
Uniprot ID:
Molecular weight:
P1,P4-Bis(5'-xanthosyl) tetraphosphate + Water → Xanthosine 5-triphosphate + Xanthylic aciddetails