Record Information
Version1.0
Creation date2011-09-21 00:05:26 UTC
Update date2015-07-21 06:56:53 UTC
Primary IDFDB021932
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 3.6.1.17 ) and nucleoside-triphosphate pyrophosphatase (EC 3.6.1.19). (KEGG) [HMDB]
CAS Number6253-56-1
Structure
Thumb
Synonyms
SynonymSource
O(5')-(Tetrahydroxytriphosphoryl)xanthosineChEBI
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
5'-XTPHMDB
Xanthosine mono(tetrahydrogen triphosphate)HMDB
XTPHMDB
Xanthosine 5'-triphosphate 2Sodium saltHMDB
O(5')-(Tetrahydroxytrioryl)xanthosineChEBI
Xanthosine 5'-triateChEBI
Xanthosine 5'-triic acidGenerator
Xanthosine 5'-triphosphic acidhmdb
Xanthosine mono(tetrahydrogen triate)HMDB
Xanthosine triateChEBI
Xanthosine triic acidGenerator
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H15N4O15P3
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
InChI IdentifierInChI=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
InChI KeyCAEFEWVYEZABLA-UUOKFMHZSA-N
Isomeric SMILESO[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
Average Molecular Weight524.1652
Monoisotopic Molecular Weight523.974675366
Classification
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
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSXanthosine 5-triphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a6s-8956230000-c953b27fc23e558f8bc3Spectrum
Predicted GC-MSXanthosine 5-triphosphate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmi-3120921000-30ff3765201db0daec17Spectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSXanthosine 5-triphosphate, TMS_2_17, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0911220000-7c9e13bd8e928a2e5785Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-840c07c15dbc79ad0f2eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-bd6b424553d786306979Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kor-1830690000-f39abfd999faa04d6195Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kbf-9620000000-5b4fb80ecb79a0415518Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9710000000-ed7594e6df7e2139120bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900010000-34d38de7734016d84840Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-80965add49e2ab233b2cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-0982000000-f089c3e029edf74721dcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000190000-79bde14d72b9665fa816Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9710120000-bccf656c48d8b7c059faSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200100000-d64535400bb7e16803e7Spectrum
NMRNot Available
ChemSpider ID388429
ChEMBL IDNot Available
KEGG Compound IDC00700
Pubchem Compound ID439296
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00293
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35735
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDXTP
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference