Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 10:25:49 -0600 |
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Update Date | 2015-06-03 15:53:27 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Xanthosine 5-triphosphate |
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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. 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. |
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Structure | |
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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
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Chemical Formula: | C10H15N4O15P3 |
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Weight: | Average: 524.1652 Monoisotopic: 523.974675366 |
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InChI Key: | CAEFEWVYEZABLA-UUOKFMHZSA-N |
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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 |
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CAS number: | 6253-56-1 |
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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 |
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Traditional IUPAC Name: | xanthosine 5-triphosphate |
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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 |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Purine nucleotides |
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Sub Class | Purine ribonucleotides |
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Direct Parent | Purine ribonucleoside triphosphates |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Solid |
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Charge: | -3 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Collection of Reactions without pathways | PW001891 | |
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KEGG Pathways: | |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a6s-8956230000-c953b27fc23e558f8bc3 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0fmi-3120921000-30ff3765201db0daec17 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_17) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0911220000-7c9e13bd8e928a2e5785 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-840c07c15dbc79ad0f2e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-1900000000-bd6b424553d786306979 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0kor-1830690000-f39abfd999faa04d6195 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0kbf-9620000000-5b4fb80ecb79a0415518 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-056r-9710000000-ed7594e6df7e2139120b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0900010000-34d38de7734016d84840 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-80965add49e2ab233b2c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uxr-0982000000-f089c3e029edf74721dc | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0000190000-79bde14d72b9665fa816 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9710120000-bccf656c48d8b7c059fa | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200100000-d64535400bb7e16803e7 | View in MoNA |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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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
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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. |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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