Record Information
Version2.0
Creation Date2012-05-31 10:25:32 -0600
Update Date2015-06-03 15:53:27 -0600
Secondary Accession Numbers
  • ECMDB00285
Identification
Name:Uridine triphosphate
DescriptionUridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety. Uridine triphosphate has the role of a source of energy or an activator of substrates in metabolic reactions, like that of adenosine triphosphate, but more specific. When Uridine triphosphate activates a substrate, UDP-substrate is usually formed and inorganic phosphate is released. (Wikipedia)
Structure
Thumb
Synonyms:
  • 5'-UTP
  • Uridine 5'-triphosphate
  • Uridine 5'-triphosphoric acid
  • Uridine mono(tetrahydrogen triphosphate)
  • Uridine mono(tetrahydrogen triphosphoric acid)
  • Uridine triphosphate
  • Uridine triphosphoric acid
  • Uridine-5'-triphosphate
  • Uridine-5'-triphosphoric acid
  • Uridine-triphosphate
  • Uridine-triphosphoric acid
  • Uteplex
  • UTP
Chemical Formula:C9H15N2O15P3
Weight:Average: 484.1411
Monoisotopic: 483.968527356
InChI Key:PGAVKCOVUIYSFO-XVFCMESISA-N
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
CAS number:63-39-8
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
Traditional IUPAC Name:uridine 5'-triphosphoric acid
SMILES:O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine ribonucleotides
Direct ParentPyrimidine ribonucleoside triphosphates
Alternative Parents
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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.37 g/LALOGPS
logP-0.07ALOGPS
logP-3.4ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area258.92 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity85.18 m³·mol⁻¹ChemAxon
Polarizability35.38 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2 Flavodoxin reduced + 2 Hydrogen ion + Uridine triphosphate > Deoxyuridine triphosphate +2 flavodoxin semi oxidized + Water
Adenosine triphosphate + Uridine 5'-diphosphate <> ADP + Uridine triphosphate
Glucose 1-phosphate + Hydrogen ion + Uridine triphosphate <> Pyrophosphate + UDP-Glucose
Adenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + Phosphate
Water + Uridine triphosphate > Hydrogen ion + Pyrophosphate + Uridine 5'-monophosphate
N-Acetyl-glucosamine 1-phosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
Uridine triphosphate + Glucose 1-phosphate <> Pyrophosphate + UDP-Glucose
Uridine triphosphate + Glucosamine-1P <> Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
Uridine triphosphate + RNA <> Pyrophosphate + RNA
Uridine triphosphate + Cytidine <> Uridine 5'-diphosphate + Cytidine monophosphate
Cytidine triphosphate + Water <> Uridine triphosphate + Ammonia
Adenosine triphosphate + Uridine triphosphate + Ammonia <> ADP + Phosphate + Cytidine triphosphate
Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water <> ADP + Phosphate + Cytidine triphosphate + L-Glutamate
Uridine triphosphate + Water <> Uridine 5'-monophosphate + Pyrophosphate
Uridine triphosphate + Uridine <> Uridine 5'-diphosphate + Uridine 5'-monophosphate
Deoxyuridine triphosphate + Thioredoxin disulfide + Water <> Uridine triphosphate + Thioredoxin
Uridine triphosphate + D-Tagatose 6-phosphate <> Uridine 5'-diphosphate + D-Tagatose 1,6-bisphosphate
Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water > Hydrogen ion + ADP + Phosphate + Cytidine triphosphate + L-Glutamate
Hydrogen ion + Glucose 1-phosphate + Uridine triphosphate > UDP-Glucose + Pyrophosphate
Hydrogen ion + <i>N</i>-acetyl-&alpha;-D-glucosamine 1-phosphate + Uridine triphosphate > Uridine diphosphate-N-acetylglucosamine + Pyrophosphate
Uridine 5'-diphosphate + Adenosine triphosphate > Uridine triphosphate + ADP
Uridine triphosphate + Alpha-D-glucose 1-phosphate > Pyrophosphate + UDP-Glucose
Uridine triphosphate + N-acetyl-alpha-D-glucosamine 1-phosphate > Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
Uridine triphosphate + [protein-PII] > Pyrophosphate + uridylyl-[protein-PII]
Adenosine triphosphate + Uridine triphosphate + Ammonia > ADP + Inorganic phosphate + Cytidine triphosphate
Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water + Ammonia <> ADP + Phosphate + Cytidine triphosphate + L-Glutamate
Uridine triphosphate + [Protein-PII] <> Pyrophosphate + Uridylyl-[protein-PII]
Glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + UDP-Glucose
β-D-glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > UDP-Glucose + Pyrophosphate
Alpha-D-glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + UDP-Glucose
N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate + Hydrogen ion + N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate > Uridine diphosphate-N-acetylglucosamine + Pyrophosphate
Uridine 5'-diphosphate + Adenosine triphosphate + Uridine 5'-diphosphate > Uridine triphosphate + Adenosine diphosphate + Uridine triphosphate + ADP
Uridine triphosphate + a reduced flavodoxin + Uridine triphosphate > Water + an oxidized flavodoxin + Deoxyuridine triphosphate
Uridine triphosphate + L-Glutamine + Water + Adenosine triphosphate + Uridine triphosphate > Adenosine diphosphate + Hydrogen ion + Phosphate + L-Glutamic acid + Cytidine triphosphate + ADP + L-Glutamate
Glucose 1-phosphate + Hydrogen ion + Uridine triphosphate <> Pyrophosphate + UDP-Glucose
Uridine triphosphate + Glucose 1-phosphate <> Pyrophosphate + UDP-Glucose
Adenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + Phosphate
Uridine triphosphate + [Protein-PII] <> Pyrophosphate + Uridylyl-[protein-PII]
Adenosine triphosphate + Uridine 5'-diphosphate <> ADP + Uridine triphosphate
Uridine triphosphate + Glucosamine-1P <> Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
Adenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + Phosphate
Uridine triphosphate + [Protein-PII] <> Pyrophosphate + Uridylyl-[protein-PII]
Adenosine triphosphate + Uridine 5'-diphosphate <> ADP + Uridine triphosphate
More...

SMPDB Pathways:
1,6-anhydro-<i>N</i>-acetylmuramic acid recyclingPW002064 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IPW000886 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IIIPW000895 ThumbThumb?image type=greyscaleThumb?image type=simple
Galactose metabolismPW000821 ThumbThumb?image type=greyscaleThumb?image type=simple
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
O-antigen building blocks biosynthesisPW002089 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
colanic acid building blocks biosynthesisPW000951 ThumbThumb?image type=greyscaleThumb?image type=simple
galactose degradation/Leloir PathwayPW000884 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIPW001905 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIIPW002059 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis IPW000906 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis I 2PW002062 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
8290± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
3990± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
2370± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
663± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-6985400000-049f49dc11e3cece73cdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-3203911000-0f0cfc0a02038f8c4d23View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0100900000-e35637d37a2d10f9d444View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-124fadc6aacda233cbc6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-a7dca6b7fb654f2e8e45View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-4f39640c93c46c531ba1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-0912500000-4127d254daa1f907106bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1921100000-79ead41c01d157630e3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900200000-1e49702931dc8a0616faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3901000000-9e6c30251cef88879070View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-7dd9d18bd041b36c39c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ql-3420900000-bdedb290606a4f13570eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06wc-9430100000-e99725c1e87e0bb4d74bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9510000000-3cdeab5c42d219775293View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001900000-aa7f3b8519a1107e3a77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9852200000-8c560690006568be20e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9401000000-8514bc75910b055190beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0503900000-79f31aa01de440e36c42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-3944800000-fe9f190dfc34341fb794View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-0921000000-115a974002fd4559fda9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Erlinge D, Harnek J, van Heusden C, Olivecrona G, Jern S, Lazarowski E: Uridine triphosphate (UTP) is released during cardiac ischemia. Int J Cardiol. 2005 Apr 28;100(3):427-33. Pubmed: 15837087
  • Holstege A, Manglitz D, Gerok W: Depletion of blood plasma cytidine due to increased hepatocellular salvage in D-galactosamine-treated rats. Eur J Biochem. 1984 Jun 1;141(2):339-44. Pubmed: 6734601
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • 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
  • Kunzelmann K, Mall M: Pharmacotherapy of the ion transport defect in cystic fibrosis: role of purinergic receptor agonists and other potential therapeutics. Am J Respir Med. 2003;2(4):299-309. Pubmed: 14719996
  • Oosterhuis GJ, Mulder AB, Kalsbeek-Batenburg E, Lambalk CB, Schoemaker J, Vermes I: Measuring apoptosis in human spermatozoa: a biological assay for semen quality? Fertil Steril. 2000 Aug;74(2):245-50. Pubmed: 10927039
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15713
HMDB IDHMDB00285
Pubchem Compound ID6133
Kegg IDC00075
ChemSpider ID5903
WikipediaUridine triphosphate
BioCyc IDUTP
EcoCyc IDUTP
Ligand ExpoUTP

Enzymes

General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
pfkB
Uniprot ID:
P06999
Molecular weight:
32456
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate
Gene Name:
ndk
Uniprot ID:
P0A763
Molecular weight:
15463
Reactions
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate.
General function:
Involved in ATP binding
Specific function:
ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
pfkA
Uniprot ID:
P0A796
Molecular weight:
34842
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.
General function:
Involved in CTP synthase activity
Specific function:
Catalyzes the ATP-dependent amination of UTP to CTP with either L-glutamine or ammonia as the source of nitrogen
Gene Name:
pyrG
Uniprot ID:
P0A7E5
Molecular weight:
60374
Reactions
ATP + UTP + NH(3) = ADP + phosphate + CTP.
General function:
Involved in DNA-directed RNA polymerase activity
Specific function:
DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. This subunit plays an important role in subunit assembly since its dimerization is the first step in the sequential assembly of subunits to form the holoenzyme
Gene Name:
rpoA
Uniprot ID:
P0A7Z4
Molecular weight:
36511
Reactions
Nucleoside triphosphate + RNA(n) = diphosphate + RNA(n+1).
General function:
Involved in DNA-directed RNA polymerase activity
Specific function:
Promotes RNA polymerase assembly. Latches the N- and C- terminal regions of the beta' subunit thereby facilitating its interaction with the beta and alpha subunits
Gene Name:
rpoZ
Uniprot ID:
P0A800
Molecular weight:
10237
Reactions
Nucleoside triphosphate + RNA(n) = diphosphate + RNA(n+1).
General function:
Involved in ATP binding
Specific function:
ATP + uridine = ADP + UMP
Gene Name:
udk
Uniprot ID:
P0A8F4
Molecular weight:
24353
Reactions
ATP + uridine = ADP + UMP.
ATP + cytidine = ADP + CMP.
General function:
Involved in DNA binding
Specific function:
DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates
Gene Name:
rpoC
Uniprot ID:
P0A8T7
Molecular weight:
155159
Reactions
Nucleoside triphosphate + RNA(n) = diphosphate + RNA(n+1).
General function:
Involved in DNA binding
Specific function:
DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates
Gene Name:
rpoB
Uniprot ID:
P0A8V2
Molecular weight:
150631
Reactions
Nucleoside triphosphate + RNA(n) = diphosphate + RNA(n+1).
General function:
Involved in [formate-C-acetyltransferase]-activating enzyme activity
Specific function:
Activation of anaerobic ribonucleoside-triphosphate reductase under anaerobic conditions by generation of an organic free radical, using S-adenosylmethionine and reduced flavodoxin as cosubstrates to produce 5'-deoxy-adenosine
Gene Name:
nrdG
Uniprot ID:
P0A9N8
Molecular weight:
17446
General function:
Involved in enzyme regulator activity
Specific function:
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose
Gene Name:
galF
Uniprot ID:
P0AAB6
Molecular weight:
32829
Reactions
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose.
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the last two sequential reactions in the de novo biosynthetic pathway for UDP-GlcNAc. Responsible for the acetylation of Glc-N-1-P to give GlcNAc-1-P and for the uridyl transfer from UTP to GlcNAc-1-P which produces UDP-GlcNAc
Gene Name:
glmU
Uniprot ID:
P0ACC7
Molecular weight:
49190
Reactions
Acetyl-CoA + alpha-D-glucosamine 1-phosphate = CoA + N-acetyl-alpha-D-glucosamine 1-phosphate.
UTP + N-acetyl-alpha-D-glucosamine 1-phosphate = diphosphate + UDP-N-acetyl-D-glucosamine.
General function:
Involved in UTP:glucose-1-phosphate uridylyltransferase activity
Specific function:
May play a role in stationary phase survival
Gene Name:
galU
Uniprot ID:
P0AEP3
Molecular weight:
32942
Reactions
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose.
General function:
Involved in nucleoside-triphosphate diphosphatase activity
Specific function:
Specific function unknown
Gene Name:
mazG
Uniprot ID:
P0AEY3
Molecular weight:
30412
Reactions
ATP + H(2)O = AMP + diphosphate.
General function:
Involved in amino acid binding
Specific function:
Modifies, by uridylylation or deuridylylation the PII (glnB) regulatory protein
Gene Name:
glnD
Uniprot ID:
P27249
Molecular weight:
102389
Reactions
UTP + [protein-PII] = diphosphate + uridylyl-[protein-PII].
General function:
Involved in dCTP deaminase activity
Specific function:
dCTP + H(2)O = dUTP + NH(3)
Gene Name:
dcd
Uniprot ID:
P28248
Molecular weight:
21249
Reactions
dCTP + H(2)O = dUTP + NH(3).
General function:
Involved in oxidoreductase activity
Specific function:
Transports electrons between flavodoxin or ferredoxin and NADPH. Involved in the reductive activation of cobalamin- independent methionine synthase, pyruvate formate lyase and anaerobic ribonucleotide reductase. Also protects against superoxide radicals due to methyl viologen in the presence of oxygen
Gene Name:
fpr
Uniprot ID:
P28861
Molecular weight:
27751
Reactions
2 reduced ferredoxin + NADP(+) + H(+) = 2 oxidized ferredoxin + NADPH.
General function:
Involved in catalytic activity
Specific function:
2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin
Gene Name:
nrdD
Uniprot ID:
P28903
Molecular weight:
80022
Reactions
2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin.
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 ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. This small ubiquitous enzyme involved in the energy metabolism and nucleotide synthesis, is essential for maintenance and cell growth
Gene Name:
adk
Uniprot ID:
P69441
Molecular weight:
23586
Reactions
ATP + AMP = 2 ADP.
General function:
Involved in FMN binding
Specific function:
Low-potential electron donor to a number of redox enzymes (Potential)
Gene Name:
fldB
Uniprot ID:
P0ABY4
Molecular weight:
19700
General function:
Involved in FMN binding
Specific function:
Low-potential electron donor to a number of redox enzymes (Potential). Involved in the reactivation of inactive cob(II)alamin in methionine synthase
Gene Name:
fldA
Uniprot ID:
P61949
Molecular weight:
19737

Transporters

General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate
Gene Name:
ndk
Uniprot ID:
P0A763
Molecular weight:
15463
Reactions
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate.