| Common Name |
Xanthosine 5-triphosphate
| Description |
Xanthosine 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).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
O(5')-(Tetrahydroxytriphosphoryl)xanthosineChEBI
Triphopsphoric acid 1-xanthosin-5'-yl esterChEBI
Xanthosine 5'-triphosphateChEBI
Xanthosine triphosphateChEBI
Xanthosine 5-triphosphoric acidGenerator
Triphopsphate 1-xanthosin-5'-yl esterGenerator
Triphopsphic acid 1-xanthosin-5'-yl esterGenerator
Xanthosine 5'-triphosphoric acidGenerator
Xanthosine triphosphoric acidGenerator
5'-XTPHMDB
Xanthosine mono(tetrahydrogen triphosphate)HMDB
XTPHMDB
Xanthosine 5'-triphosphate 2Sodium saltMeSH
| Chemical Formlia |
C10H15N4O15P3
| Average Molecliar Weight |
524.1652
| Monoisotopic Molecliar Weight |
523.974675366
| 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 Name |
xanthosine 5-triphosphate
| CAS Registry Number |
6253-56-1
| 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
| InChI Identifier |
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
| InChI Key |
CAEFEWVYEZABLA-UUOKFMHZSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Nucleosides, nucleotides, and analogues
| Sub Class |
Purine nucleotides
| Direct Parent |
Purine ribonucleoside triphosphates
| Alternative Parents |
Purine ribonucleoside monophosphates
Pentose phosphates
Xanthines
Glycosylamines
Monosaccharide phosphates
Alkaloids and derivatives
Hydroxypyrimidines
Monoalkyl phosphates
N-substituted imidazoles
Oxolanes
Heteroaromatic compounds
Secondary alcohols
1,2-diols
Oxacyclic compounds
Azacyclic compounds
Organopnictogen compounds
Hydrocarbon derivatives
Organonitrogen compounds
Organic oxides
| 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
Monosaccharide
Pyrimidine
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Azole
Imidazole
Oxolane
Heteroaromatic compound
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
xanthosine 5'-phosphate (CHEBI:10049 )
purine ribonucleoside 5'-triphosphate (CHEBI:10049 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Energy currency, DNA/RNA synthesis, Enzyme cofactors, signaling
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility4.04 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity95.02 m3·mol-1ChemAxon
Polarizability39.11 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-0udi-0911220000-7c9e13bd8e928a2e5785View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0udi-0900000000-840c07c15dbc79ad0f2eView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0udi-1900000000-bd6b424553d786306979View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-0kor-1830690000-f39abfd999faa04d6195View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-0kbf-9620000000-5b4fb80ecb79a0415518View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-056r-9710000000-ed7594e6df7e2139120bView in MoNA
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Not Available
| Tissue Location |
Prostate
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021932
| KNApSAcK ID |
Not Available
| Chemspider ID |
388429
| KEGG Compound ID |
C00700
| BioCyc ID |
Not Available
| BiGG ID |
35735
| Wikipedia Link |
XTP
| NuGOwiki Link |
HMDB00293
| Metagene Link |
HMDB00293
| METLIN ID |
Not Available
| PubChem Compound |
439296
| PDB ID |
Not Available
| ChEBI ID |
10049
Product: Bay 41-4109 (racemate)
References |
| 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 |
| General References |
- 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 ]
- 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 ]
|
Enzymes
- 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
Reactions
| Xanthosine 5-triphosphate + Water → Xanthylic acid + Pyrophosphate |
details |
- 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:
- NUDT2
- Uniprot ID:
- P50583
- Molecular weight:
- 16829.09
Reactions
| P1,P4-Bis(5'-xanthosyl) tetraphosphate + Water → Xanthosine 5-triphosphate + Xanthylic acid |
details |
PMID: 22907667