Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:14 UTC
HMDB IDHMDB00285
Secondary Accession NumbersNone
Metabolite Identification
Common NameUridine 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
  1. 5'-UTP
  2. Uridine 5'-triphosphate
  3. Uridine mono(tetrahydrogen triphosphate)
  4. Uridine triphosphate
  5. Uteplex
  6. UTP
Chemical FormulaC9H15N2O15P3
Average Molecular Weight484.1411
Monoisotopic Molecular Weight483.968527356
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({[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
CAS Registry Number63-39-8
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
InChI Identifier
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
InChI KeyPGAVKCOVUIYSFO-XVFCMESISA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPyrimidine Nucleotides
Sub ClassPyrimidine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Ribonucleotides(KEGG)
  • pyrimidine ribonucleoside 5'-triphosphate(ChEBI)
  • uridine 5'-phosphate(ChEBI)
Substituents
  • 1,2 Diol
  • Glycosyl Compound
  • Hydropyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct ParentPyrimidine Ribonucleoside Triphosphates
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminosugars metabolism
  • Component of Galactose metabolism
  • Component of Nucleotide sugars metabolism
  • Component of Pyrimidine metabolism
  • Component of Starch and sucrose metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 area258.92ChemAxon
rotatable bond count8ChemAxon
refractivity85.18ChemAxon
polarizability35.37ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Nucleus
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045map00520
DNA Replication ForkSMP00477Not Available
Lactose SynthesisSMP00444Not Available
Pyrimidine MetabolismSMP00046map00240
Transcription/TranslationSMP00019Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021929
KNApSAcK IDNot Available
Chemspider ID5903
KEGG Compound IDC00075
BioCyc IDUTP
BiGG ID33760
Wikipedia LinkUridine triphosphate
NuGOwiki LinkHMDB00285
Metagene LinkHMDB00285
METLIN ID5277
PubChem Compound6133
PDB IDUTP
ChEBI ID15713
References
Synthesis ReferenceKenner, 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
General References
  1. 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
  2. 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
  3. 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
  4. 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

Only showing the first 50 proteins. There are 65 proteins in total.

Enzymes

Gene Name:
ENTPD1
Uniprot ID:
P49961
Reactions
Uridine triphosphate + Water unknown Uridine 5'-diphosphate + Phosphoric aciddetails
Gene Name:
ENTPD3
Uniprot ID:
O75355
Reactions
Uridine triphosphate + Water unknown Uridine 5'-diphosphate + Phosphoric aciddetails
Gene Name:
UCK1
Uniprot ID:
Q9HA47
Reactions
Uridine triphosphate + Cytidine unknown Uridine 5'-diphosphate + Cytidine monophosphatedetails
Uridine triphosphate + Uridine unknown Uridine 5'-diphosphate + Uridine 5'-monophosphatedetails
Gene Name:
NME4
Uniprot ID:
O00746
Reactions
Adenosine triphosphate + Uridine 5'-diphosphate unknown ADP + Uridine triphosphatedetails
Gene Name:
NME1
Uniprot ID:
P15531
Reactions
Adenosine triphosphate + Uridine 5'-diphosphate unknown ADP + Uridine triphosphatedetails
Gene Name:
NME7
Uniprot ID:
Q9Y5B8
Reactions
Adenosine triphosphate + Uridine 5'-diphosphate unknown ADP + Uridine triphosphatedetails
Gene Name:
NME2
Uniprot ID:
P22392
Reactions
Adenosine triphosphate + Uridine 5'-diphosphate unknown ADP + Uridine triphosphatedetails
Gene Name:
NME3
Uniprot ID:
Q13232
Reactions
Adenosine triphosphate + Uridine 5'-diphosphate unknown ADP + Uridine triphosphatedetails
Gene Name:
NME6
Uniprot ID:
O75414
Reactions
Adenosine triphosphate + Uridine 5'-diphosphate unknown ADP + Uridine triphosphatedetails
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Reactions
Uridine triphosphate + Water unknown Uridine 5'-monophosphate + Pyrophosphatedetails
Gene Name:
AK3
Uniprot ID:
Q9UIJ7
Reactions
Uridine triphosphate + Adenosine monophosphate unknown Uridine 5'-diphosphate + ADPdetails
Gene Name:
NUDT2
Uniprot ID:
P50583
Reactions
P1,P4-Bis(5'-uridyl) tetraphosphate + Water unknown Uridine triphosphate + Uridine 5'-monophosphatedetails
Gene Name:
CTPS1
Uniprot ID:
P17812
Reactions
Adenosine triphosphate + Uridine triphosphate + Ammonia unknown ADP + Phosphoric acid + Cytidine triphosphatedetails
Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water unknown ADP + Phosphoric acid + Cytidine triphosphate + L-Glutamic aciddetails
Gene Name:
PFKP
Uniprot ID:
Q01813
Reactions
Uridine triphosphate + D-Tagatose 6-phosphate unknown Uridine 5'-diphosphate + D-Tagatose 1,6-bisphosphatedetails
Gene Name:
POLR3D
Uniprot ID:
P05423
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR2B
Uniprot ID:
P30876
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR2A
Uniprot ID:
P24928
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR1B
Uniprot ID:
Q9H9Y6
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR3G
Uniprot ID:
O15318
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR3B
Uniprot ID:
Q9NW08
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR1E
Uniprot ID:
Q9GZS1
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
PFKL
Uniprot ID:
P17858
Reactions
Uridine triphosphate + D-Tagatose 6-phosphate unknown Uridine 5'-diphosphate + D-Tagatose 1,6-bisphosphatedetails
Gene Name:
POLR3H
Uniprot ID:
Q9Y535
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR3K
Uniprot ID:
Q9Y2Y1
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
PFKM
Uniprot ID:
P08237
Reactions
Uridine triphosphate + D-Tagatose 6-phosphate unknown Uridine 5'-diphosphate + D-Tagatose 1,6-bisphosphatedetails
Gene Name:
PKM
Uniprot ID:
P14618
Gene Name:
PKLR
Uniprot ID:
P30613
Gene Name:
UGP2
Uniprot ID:
Q16851
Reactions
Uridine triphosphate + Glucose 1-phosphate unknown Pyrophosphate + Uridine diphosphate glucosedetails
Gene Name:
UAP1
Uniprot ID:
Q16222
Reactions
Uridine triphosphate + N-acetyl-alpha-D-galactosamine 1-phosphate unknown Pyrophosphate + UDP-N-acetyl-alpha-D-galactosaminedetails
Uridine triphosphate + N-Acetyl-glucosamine 1-phosphate unknown Pyrophosphate + Uridine diphosphate-N-acetylglucosaminedetails
Gene Name:
UCK2
Uniprot ID:
Q9BZX2
Reactions
Uridine triphosphate + Cytidine unknown Uridine 5'-diphosphate + Cytidine monophosphatedetails
Uridine triphosphate + Uridine unknown Uridine 5'-diphosphate + Uridine 5'-monophosphatedetails
Gene Name:
CAD
Uniprot ID:
P27708
Gene Name:
CTPS2
Uniprot ID:
Q9NRF8
Reactions
Adenosine triphosphate + Uridine triphosphate + Ammonia unknown ADP + Phosphoric acid + Cytidine triphosphatedetails
Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water unknown ADP + Phosphoric acid + Cytidine triphosphate + L-Glutamic aciddetails
Gene Name:
UCKL1
Uniprot ID:
Q9NWZ5
Reactions
Uridine triphosphate + Cytidine unknown Uridine 5'-diphosphate + Cytidine monophosphatedetails
Uridine triphosphate + Uridine unknown Uridine 5'-diphosphate + Uridine 5'-monophosphatedetails
Gene Name:
ENTPD8
Uniprot ID:
Q5MY95
Reactions
Uridine triphosphate + Water unknown Uridine 5'-diphosphate + Phosphoric aciddetails
Gene Name:
POLR3A
Uniprot ID:
O14802
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR1A
Uniprot ID:
O95602
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
ZNRD1
Uniprot ID:
Q2L6J2
Gene Name:
POLR1D
Uniprot ID:
Q9Y2S0
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
DKFZp686D10173
Uniprot ID:
Q7Z3R8
Gene Name:
POLR3GL
Uniprot ID:
Q9BT43
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR1C
Uniprot ID:
Q96HT3
Gene Name:
NME5
Uniprot ID:
P56597
Reactions
Adenosine triphosphate + Uridine 5'-diphosphate unknown ADP + Uridine triphosphatedetails
Gene Name:
ZNRD1
Uniprot ID:
Q9P1U0
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
TWISTNB
Uniprot ID:
Q3B726
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR2E
Uniprot ID:
P19388
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR2F
Uniprot ID:
P61218
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR2H
Uniprot ID:
P52434
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR2K
Uniprot ID:
P53803
Reactions
Uridine triphosphate + RNA unknown Pyrophosphate + RNAdetails

Only showing the first 50 proteins. There are 65 proteins in total.