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Record Information
Version1.0
Creation Date2016-09-30 22:27:49 UTC
Update Date2020-05-21 16:29:00 UTC
BMDB IDBMDB0000285
Secondary Accession Numbers
  • BMDB00285
Metabolite Identification
Common NameUridine triphosphate
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.
Structure
Thumb
Synonyms
ValueSource
5'-UTPChEBI
H4UTPChEBI
Uridine 5'-triphosphateChEBI
Uridine 5'-triphosphoric acidChEBI
Uridine triphosphoric acidGenerator
Uridine mono(tetrahydrogen triphosphate)HMDB
UteplexHMDB
UTPHMDB
MG UTPHMDB
Magnesium UTPHMDB
Magnesium uridine triphosphateHMDB
Triphosphate, uridineHMDB
MG-UTPHMDB
Triphosphate, magnesium uridineHMDB
UTP, MagnesiumHMDB
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 Nameuridine 5'-triphosphoric 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
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • 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
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 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 AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000285
DrugBank IDDB04005
Phenol Explorer Compound IDNot Available
FooDB IDFDB031251
KNApSAcK IDNot Available
Chemspider ID5903
KEGG Compound IDC00075
BioCyc IDUTP
BiGG ID33760
Wikipedia LinkUridine triphosphate
METLIN ID5277
PubChem Compound6133
PDB IDNot Available
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 ReferencesNot Available

Enzymes

General function:
Nucleotide transport and metabolism
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 (By similarity).
Gene Name:
NME7
Uniprot ID:
Q5E9Y9
Molecular weight:
42599.0
Reactions
Uridine triphosphate + ADP → Uridine 5'-diphosphate + Adenosine triphosphatedetails
General function:
Nucleotide transport and metabolism
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 (By similarity). Negatively regulates Rho activity by interacting with AKAP13/LBC. Acts as a transcriptional activator of the MYC gene; binds DNA non-specifically. Binds to both single-stranded guanine- and cytosine-rich strands within the nuclease hypersensitive element (NHE) III(1) region of the MYC gene promoter. Does not bind to duplex NHE III(1). Has G-quadruplex (G4) DNA-binding activity, which is independent of its nucleotide-binding and kinase activity. Binds both folded and unfolded G4 with similar low nanomolar affinities. Stabilizes folded G4s regardless of whether they are prefolded or not (By similarity). Exhibits histidine protein kinase activity (PubMed:12486123).
Gene Name:
NME2
Uniprot ID:
Q3T0Q4
Molecular weight:
17316.0
Reactions
Adenosine triphosphate + Uridine 5'-diphosphate → ADP + Uridine triphosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q2KIC5
Molecular weight:
23061.0
Reactions
Uridine triphosphate + Water → Uridine 5'-monophosphate + Pyrophosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Involved in maintaining the homeostasis of cellular nucleotides by catalyzing the interconversion of nucleoside phosphates. Has GTP:AMP phosphotransferase and ITP:AMP phosphotransferase activities.
Gene Name:
AK3
Uniprot ID:
P08760
Molecular weight:
25671.0
Reactions
Uridine 5'-diphosphate + ADP → Uridine triphosphate + 3'-AMPdetails
General function:
Involved in UTP:glucose-1-phosphate uridylyltransferase
Specific function:
Plays a central role as a glucosyl donor in cellular metabolic pathways.
Gene Name:
UGP2
Uniprot ID:
Q07130
Molecular weight:
56903.0
Reactions
Glucose 1-phosphate + Uridine triphosphate → Uridine diphosphate glucose + Pyrophosphatedetails
Uridine diphosphate glucose + Pyrophosphate → Glucose 1-phosphate + Uridine triphosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes the ATP-dependent amination of UTP to CTP with either L-glutamine or ammonia as the source of nitrogen. Constitutes the rate-limiting enzyme in the synthesis of cytosine nucleotides (By similarity).
Gene Name:
CTPS2
Uniprot ID:
Q1RMS2
Molecular weight:
65481.0
Reactions
Uridine triphosphate + Adenosine triphosphate → Cytidine triphosphate + ADP + Hydrogen phosphate + dCTPdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
UAP1
Uniprot ID:
F1MJP7
Molecular weight:
58623.0
Reactions
N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate → Uridine diphosphate-N-acetylglucosamine + Pyrophosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
CANT1
Uniprot ID:
E1BGL5
Molecular weight:
44706.0
Reactions
Uridine triphosphate + Water → Uridine 5'-diphosphate + Hydrogen phosphatedetails