Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000117
Name: Uridine triphosphate
Description:Uridine 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)
  • 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
Average Molecular Weight: 484.1411
Monoisotopic Molecular Weight: 483.968527356
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
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyrimidine ribonucleoside triphosphates. These are pyrimidine ribobucleotides with triphosphate group linked to the ribose moiety.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Pyrimidine nucleotides
Sub ClassPyrimidine ribonucleotides
Direct Parent Pyrimidine ribonucleoside triphosphates
Alternative Parents
  • Pyrimidine ribonucleoside triphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydropyrimidine
  • Saccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Urea
  • Secondary alcohol
  • Lactam
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Melting point: Not Available
Experimental Properties:
Predicted Properties
Water Solubility8.37 mg/mLALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area258.92 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity85.18 m3·mol-1ChemAxon
Polarizability35.37 Å3ChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
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
Hydrogen ion + <i>N</i>-acetyl-&alpha;-D-glucosamine 1-phosphate + Uridine triphosphate > Uridine diphosphate-N-acetylglucosamine + Pyrophosphate

Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
  • 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:
Pubchem Compound ID6133
Kegg IDC00075
ChemSpider ID5903
WikipediaUridine triphosphate
Ligand ExpoUTP


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:
Locus Tag:
Molecular weight:
15.6 kDa
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate.
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:
Locus Tag:
Molecular weight:
59.6 kDa
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:
Locus Tag:
Molecular weight:
36.6 kDa
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:
Locus Tag:
Molecular weight:
9.8 kDa
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:
Locus Tag:
Molecular weight:
154.4 kDa
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:
Locus Tag:
Molecular weight:
150.8 kDa
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:
Locus Tag:
Molecular weight:
25.7 kDa
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:
Locus Tag:
Molecular weight:
48.9 kDa
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:
Locus Tag:
Molecular weight:
31.2 kDa
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose.
General function:
Involved in nucleoside-triphosphate diphosphatase activity
Specific function:
Specific function unknown
Gene Name:
Locus Tag:
Molecular weight:
31.2 kDa
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:
Locus Tag:
Molecular weight:
103.4 kDa
UTP + [protein-PII] = diphosphate + uridylyl-[protein-PII].
General function:
Involved in catalytic activity
Specific function:
2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin
Gene Name:
Locus Tag:
Molecular weight:
76.1 kDa
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:
Locus Tag:
Molecular weight:
21.2 kDa
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:
Locus Tag:
Molecular weight:
23.1 kDa
ATP + AMP = 2 ADP.