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Identification
YMDB IDYMDB00326
NameUridine triphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionUridine 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, N-acetyl-glucosamine 1-phosphate and uridine triphosphate can be converted into uridine diphosphate-N-acetylglucosamine; which is mediated by the enzyme UDP-N-acetylglucosamine pyrophosphorylase. In addition, glucose 1-phosphate and uridine triphosphate can be converted into uridine diphosphate glucose and UDP through the action of the enzyme uridinephosphoglucose pyrophosphorylase. In yeast, uridine triphosphate is involved in the metabolic pathway called the amino sugar and nucleotide sugar metabolism pathway.
Structure
Thumb
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
CAS number63-39-8
WeightAverage: 484.1411
Monoisotopic: 483.968527356
InChI KeyPGAVKCOVUIYSFO-XVFCMESISA-N
InChIInChI=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
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 Nameuridine 5'-triphosphoric acid
Chemical FormulaC9H15N2O15P3
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
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Polarizability35.37 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
Leloir PathwayPW002397 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW002469 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Pyrimidine metabolismec00240 Map00240
Starch and sucrose metabolismec00500 Map00500
SMPDB Reactions
Glucose 1-phosphate + Uridine triphosphate + hydronUridine diphosphate glucose + Uridine 5'-diphosphate
N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate + hydronPyrophosphate + Uridine diphosphate-N-acetylglucosamine
Uridine 5'-diphosphate + Adenosine triphosphateUridine triphosphate + ADP
Uridine triphosphate + L-Glutamine + water + Adenosine triphosphateADP + hydron + phosphate + L-Glutamic acid + Cytidine triphosphate
Uridine triphosphate + a reduced flavodoxin → water + an oxidized flavodoxin + Deoxyuridine triphosphate
KEGG Reactions
Uridine triphosphate + Adenosine triphosphate + water + L-Glutaminephosphate + L-Glutamic acid + hydron + ADP + Cytidine triphosphate
Uridine triphosphate + Adenosine triphosphate + Ammoniumphosphate + hydron + ADP + Cytidine triphosphate
Uridine triphosphate + Galactose 1-phosphate + hydronPyrophosphate + UDP-D-galactose
Uridine triphosphate + (R)-Mevalonic acidMevalonic acid-5P + Uridine 5'-diphosphate + hydron
Adenosine triphosphate + Uridine 5'-diphosphateUridine triphosphate + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
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
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.
External Links:
ResourceLink
CHEBI ID15713
HMDB IDHMDB00285
Pubchem Compound ID6133
Kegg IDC00075
ChemSpider ID5903
FOODB IDFDB021929
WikipediaUridine_triphosphate
BioCyc IDUTP

Enzymes

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:
URA7
Uniprot ID:
P28274
Molecular weight:
64709.80078
Reactions
ATP + UTP + NH(3) → ADP + phosphate + CTP.
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. Plays an important role in the regulation of phospholipid synthesis
Gene Name:
URA8
Uniprot ID:
P38627
Molecular weight:
63055.69922
Reactions
ATP + UTP + NH(3) → ADP + phosphate + CTP.
General function:
Involved in UDP-glucose:hexose-1-phosphate uridylyltransferase activity
Specific function:
UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose
Gene Name:
GAL7
Uniprot ID:
P08431
Molecular weight:
42384.69922
Reactions
UDP-glucose + alpha-D-galactose 1-phosphate → alpha-D-glucose 1-phosphate + UDP-galactose.
General function:
Involved in UDP-N-acetylglucosamine diphosphorylase act
Specific function:
UTP + N-acetyl-alpha-D-glucosamine 1-phosphate = diphosphate + UDP-N-acetyl-D-glucosamine
Gene Name:
QRI1
Uniprot ID:
P43123
Molecular weight:
53475.60156
Reactions
UTP + N-acetyl-alpha-D-glucosamine 1-phosphate → diphosphate + UDP-N-acetyl-D-glucosamine.
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of phosphoanhydride bonds of nucleoside tri- and di-phosphates. Has equal high activity toward ADP/ATP, GDP/GTP, and UDP/UTP and approximately 50% less toward CDP/CTP and thiamine pyrophosphate. Has no activity toward GMP. Required for Golgi glycosylation and cell wall integrity. Together with CDC55, required for adenovirus E4orf4 (early region 4 open reading frame 4) induced toxicity, the apyrase activity is not required for this function. Plays a role in sphingolipid synthesis
Gene Name:
YND1
Uniprot ID:
P40009
Molecular weight:
71851.20313
Reactions
ATP + 2 H(2)O → AMP + 2 phosphate.
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. Required for repair of UV radiation- and etoposide-induced DNA damage
Gene Name:
YNK1
Uniprot ID:
P36010
Molecular weight:
17166.59961
Reactions
ATP + nucleoside diphosphate → ADP + nucleoside triphosphate.
General function:
Involved in ATP binding
Specific function:
RAR (regulation of autonomous replication) is a protein whose activity increases the mitotic stability of plasmids
Gene Name:
ERG12
Uniprot ID:
P07277
Molecular weight:
48458.89844
Reactions
ATP + (R)-mevalonate → ADP + (R)-5-phosphomevalonate.
General function:
Involved in electron carrier activity
Specific function:
Participates as a hydrogen donor in redox reactions through the reversible oxidation of its active center dithiol to a disulfide, accompanied by the transfer of 2 electrons and 2 protons. It is involved in many cellular processes, including deoxyribonucleotide synthesis, repair of oxidatively damaged proteins, protein folding, sulfur metabolism, and redox homeostasis. Thioredoxin-dependent enzymes include phosphoadenosine-phosphosulfate reductase MET16, alkyl- hydroperoxide reductase DOT5, thioredoxin peroxidases TSA1 and TSA2, alkyl hydroperoxide reductase AHP1, and peroxiredoxin HYR1. Thioredoxin is also involved in protection against reducing stress. As part of the LMA1 complex, it is involved in the facilitation of vesicle fusion such as homotypic vacuole and ER- derived COPII vesicle fusion with the Golgi. This activity does not require the redox mechanism. Through its capacity to inactivate the stress response transcription factor YAP1 and its regulator the hydroperoxide stress sensor HYR1, it is involved in feedback regulation of stress response gene expression upon oxidative stress
Gene Name:
TRX2
Uniprot ID:
P22803
Molecular weight:
11203.7998
Reactions
General function:
Involved in electron carrier activity
Specific function:
Participates as a hydrogen donor in redox reactions through the reversible oxidation of its active center dithiol to a disulfide, accompanied by the transfer of 2 electrons and 2 protons. It is involved in many cellular processes, including deoxyribonucleotide synthesis, repair of oxidatively damaged proteins, protein folding, sulfur metabolism, and redox homeostasis. Thioredoxin-dependent enzymes include phosphoadenosine-phosphosulfate reductase MET16, alkyl- hydroperoxide reductase DOT5, thioredoxin peroxidases TSA1 and TSA2, alkyl hydroperoxide reductase AHP1, and peroxiredoxin HYR1. Thioredoxin is also involved in protection against reducing stress. As part of the LMA1 complex, it is involved in the facilitation of vesicle fusion such as homotypic vacuole and ER- derived COPII vesicle fusion with the Golgi. This activity does not require the redox mechanism
Gene Name:
TRX1
Uniprot ID:
P22217
Molecular weight:
11234.90039
Reactions
General function:
Involved in nucleotidyltransferase activity
Specific function:
Plays a central role as a glucosyl donor in cellular metabolic pathways
Gene Name:
Not Available
Uniprot ID:
P38709
Molecular weight:
55999.80078
Reactions
UTP + alpha-D-glucose 1-phosphate → diphosphate + UDP-glucose.
General function:
Involved in nucleotidyltransferase activity
Specific function:
Plays a central role as a glucosyl donor in cellular metabolic pathways
Gene Name:
UGP1
Uniprot ID:
P32861
Molecular weight:
55987.39844
Reactions
UTP + alpha-D-glucose 1-phosphate → diphosphate + UDP-glucose.

Transporters

General function:
Involved in binding
Specific function:
Not Available
Gene Name:
RIM2
Uniprot ID:
P38127
Molecular weight:
42101.39844