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Identification |
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YMDB ID | YMDB00326 |
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Name | Uridine triphosphate |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Uridine triphosphate, also known as 5'-UTP or H4UTP, belongs to the class of organic compounds known as pyrimidine ribonucleoside triphosphates. These are pyrimidine ribobucleotides with triphosphate group linked to the ribose moiety. Uridine triphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine triphosphate exists in all living species, ranging from bacteria to humans. Within yeast, uridine triphosphate participates in a number of enzymatic reactions. In particular, glucose 1-phosphate and uridine triphosphate can be converted into uridine diphosphate glucose; which is mediated by the enzyme UTP--glucose-1-phosphate uridylyltransferase. In addition, glucose 1-phosphate and uridine triphosphate can be converted into uridine diphosphate glucose; which is mediated by the enzyme UTP--glucose-1-phosphate uridylyltransferase. In yeast, uridine triphosphate is involved in the metabolic pathway called the starch and sucrose metabolism pathway. |
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Structure | |
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Synonyms | - 5'-UTP
- Uridine 5'-triphosphate
- Uridine mono(tetrahydrogen triphosphate)
- Uridine triphosphate
- Uridine triphosphic acid
- Uteplex
- UTP
- H4UTP
- Uridine 5'-triphosphoric acid
- Uridine triphosphoric acid
- MG UTP
- Magnesium UTP
- Magnesium uridine triphosphate
- Triphosphate, uridine
- MG-UTP
- Triphosphate, magnesium uridine
- UTP, Magnesium
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CAS number | 63-39-8 |
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Weight | Average: 484.1411 Monoisotopic: 483.968527356 |
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InChI Key | PGAVKCOVUIYSFO-XVFCMESISA-N |
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InChI | InChI=1S/C9H15N2O15P3/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 |
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IUPAC Name | ({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid |
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Traditional IUPAC Name | uridine 5'-triphosphoric acid |
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Chemical Formula | C9H15N2O15P3 |
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SMILES | [H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O[H])[C@@]1([H])O[H])N1C([H])=C([H])C(=O)N([H])C1=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as pyrimidine ribonucleoside triphosphates. These are pyrimidine ribobucleotides with 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 | Pyrimidine nucleotides |
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Sub Class | Pyrimidine ribonucleotides |
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Direct Parent | Pyrimidine ribonucleoside triphosphates |
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Alternative Parents | |
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Substituents | - Pyrimidine ribonucleoside triphosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Hydroxypyrimidine
- Pyrimidone
- Monoalkyl phosphate
- Hydropyrimidine
- Monosaccharide
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Pyrimidine
- Alkyl phosphate
- Heteroaromatic compound
- Tetrahydrofuran
- Secondary alcohol
- 1,2-diol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Organopnictogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | |
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KEGG Pathways | Amino sugar and nucleotide sugar metabolism | ec00520 | | Pyrimidine metabolism | ec00240 | | Starch and sucrose metabolism | ec00500 | |
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SMPDB Reactions |
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KEGG Reactions |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-056r-6985400000-049f49dc11e3cece73cd | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00fr-3203911000-0f0cfc0a02038f8c4d23 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0100900000-e35637d37a2d10f9d444 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0002-9000000000-124fadc6aacda233cbc6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0002-9000000000-a7dca6b7fb654f2e8e45 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0002-9000000000-4f39640c93c46c531ba1 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a59-0912500000-4127d254daa1f907106b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-1921100000-79ead41c01d157630e3a | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900200000-1e49702931dc8a0616fa | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-3901000000-9e6c30251cef88879070 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-5900000000-7dd9d18bd041b36c39c3 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-01ql-3420900000-bdedb290606a4f13570e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-06wc-9430100000-e99725c1e87e0bb4d74b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-056r-9510000000-3cdeab5c42d219775293 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0001900000-aa7f3b8519a1107e3a77 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9852200000-8c560690006568be20e4 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9401000000-8514bc75910b055190be | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01q9-0503900000-79f31aa01de440e36c42 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03e9-3944800000-fe9f190dfc34341fb794 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03fr-0921000000-115a974002fd4559fda9 | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Milewski, S., Gabriel, I., Olchowy, J. (2006). "Enzymes of UDP-GlcNAc biosynthesis in yeast." Yeast 23:1-14.16408321
- Marobbio, C. M., Di Noia, M. A., Palmieri, F. (2006). "Identification of a mitochondrial transporter for pyrimidine nucleotides in Saccharomyces cerevisiae: bacterial expression, reconstitution and functional characterization." Biochem J 393:441-446.16194150
- Gao, X. D., Kaigorodov, V., Jigami, Y. (1999). "YND1, a homologue of GDA1, encodes membrane-bound apyrase required for Golgi N- and O-glycosylation in Saccharomyces cerevisiae." J Biol Chem 274:21450-21456.10409709
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Synthesis Reference: | Kenner, G. W.; Todd, A. R.; Webb, R. F.; Weymouth, F. J. Nucleotides. XXVIII. Synthesis of uridine 5'-triphosphate. Journal of the Chemical Society (1954), 46-52 2288-93. |
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