Record Information
Version2.0
Creation Date2012-05-31 10:25:49 -0600
Update Date2015-06-03 15:53:27 -0600
Secondary Accession Numbers
  • ECMDB00293
Identification
Name:Xanthosine 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. Xanthosine 5-triphosphate is an intermediate of the Purine metabolism pathway, a substrate of the enzymes dinucleoside tetraphosphatase (EC 3.6.1.17) and nucleoside-triphosphate pyrophosphatase (EC 3.6.1.19). It is also a substrate for Xanthine triphosphatase, which is a phosphatase that hydrolyzes non-canonical purine nucleotides such as XTP and ITP to their respective diphosphate derivatives.
Structure
Thumb
Synonyms:
  • 5'-XTP
  • Xanthosine 5'-triphosphate
  • Xanthosine 5'-triphosphoric acid
  • Xanthosine 5-triphosphoric acid
  • Xanthosine mono(tetrahydrogen triphosphate)
  • Xanthosine mono(tetrahydrogen triphosphoric acid)
  • Xanthosine triphosphate
  • Xanthosine triphosphoric acid
  • XTP
Chemical Formula:C10H15N4O15P3
Weight:Average: 524.1652
Monoisotopic: 523.974675366
InChI Key:CAEFEWVYEZABLA-UUOKFMHZSA-N
InChI:InChI=1S/C10H15N4O15P3/c15-5-3(1-26-31(22,23)29-32(24,25)28-30(19,20)21)27-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1
CAS number:6253-56-1
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 IUPAC Name:xanthosine 5-triphosphate
SMILES:O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(O)N=C2O
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
Substituents
  • 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
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.04 g/LALOGPS
logP-0.45ALOGPS
logP-4.1ChemAxon
logS-2.1ALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Collection of Reactions without pathwaysPW001891 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6s-8956230000-c953b27fc23e558f8bc3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fmi-3120921000-30ff3765201db0daec17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0911220000-7c9e13bd8e928a2e5785View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-840c07c15dbc79ad0f2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-bd6b424553d786306979View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kor-1830690000-f39abfd999faa04d6195View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kbf-9620000000-5b4fb80ecb79a0415518View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9710000000-ed7594e6df7e2139120bView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:anachkov 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
External Links:
ResourceLink
CHEBI ID10049
HMDB IDHMDB00293
Pubchem Compound ID121887
Kegg IDC00700
ChemSpider ID388429
WikipediaXTP
BioCyc IDXTP
EcoCyc IDXTP

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes O6 atom-containing purine bases deoxyinosine triphosphate (dITP) and xanthosine triphosphate (XTP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) to nucleotide monophosphate and pyrophosphate. Probably excludes non- standard purines from DNA precursor pool, preventing thus incorporation into DNA and avoiding chromosomal lesions
Gene Name:
rdgB
Uniprot ID:
P52061
Molecular weight:
21039
Reactions
A nucleoside triphosphate + H(2)O = a nucleotide + diphosphate.
General function:
Involved in nucleoside-triphosphatase activity
Specific function:
Specific function unknown
Gene Name:
yjjX
Uniprot ID:
P39411
Molecular weight:
18213
Reactions
A nucleoside triphosphate + H(2)O = a nucleoside diphosphate + monophosphate.