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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-11 16:24:40 UTC
Update Date2021-09-14 15:39:00 UTC
HMDB IDHMDB0006796
Secondary Accession Numbers
  • HMDB06796
Metabolite Identification
Common NameP1,P4-Bis(5'-uridyl) tetraphosphate
DescriptionP1,P4-Bis(5'-uridyl) tetraphosphate, also known as diquafosol or uppppu, belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. P1,P4-Bis(5'-uridyl) tetraphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). A pyrimidine ribonucleoside 5'-tetraphosphate compound having 5'-uridinyl residues at the P(1)- and P(4)-positions. P1,P4-Bis(5'-uridyl) tetraphosphate exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1582752406
Synonyms
ValueSource
DiquafosolChEBI
P1,P4-Bis(5'-uridyl) tetrahydrogen tetraphosphateChEBI
UppppUKegg
P1,P4-Bis(5'-uridyl) tetrahydrogen tetraphosphoric acidGenerator
P1,P4-Bis(5'-uridyl) tetraphosphoric acidGenerator
INS 365HMDB
INS-365HMDB
p(1),p(4)-Bis(uridin-5'-yl) tetraphosphoric acidHMDB
Chemical FormulaC18H26N4O23P4
Average Molecular Weight790.3071
Monoisotopic Molecular Weight789.993829206
IUPAC Name{[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[(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)(hydroxy)phosphoryl]oxy})phosphinic acid
Traditional Namediquafosol
CAS Registry NumberNot Available
SMILES
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O)N1C=CC(=O)NC1=O
InChI Identifier
InChI=1S/C18H26N4O23P4/c23-9-1-3-21(17(29)19-9)15-13(27)11(25)7(41-15)5-39-46(31,32)43-48(35,36)45-49(37,38)44-47(33,34)40-6-8-12(26)14(28)16(42-8)22-4-2-10(24)20-18(22)30/h1-4,7-8,11-16,25-28H,5-6H2,(H,31,32)(H,33,34)(H,35,36)(H,37,38)(H,19,23,29)(H,20,24,30)/t7-,8-,11-,12-,13-,14-,15-,16-/m1/s1
InChI KeyNMLMACJWHPHKGR-NCOIDOBVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class(5'->5')-dinucleotides
Sub ClassNot Available
Direct Parent(5'->5')-dinucleotides
Alternative Parents
Substituents
  • (5'->5')-dinucleotide
  • Pyrimidine ribonucleoside polyphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Vinylogous amide
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Lactam
  • Urea
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility13.9 g/LALOGPS
logP0.36ALOGPS
logP-5.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.59ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area393.55 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity144.84 m³·mol⁻¹ChemAxon
Polarizability59.7 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+198.69730932474
DeepCCS[M-H]-196.80330932474
DeepCCS[M-2H]-230.03830932474
DeepCCS[M+Na]+204.47630932474
AllCCS[M+H]+233.332859911
AllCCS[M+H-H2O]+233.132859911
AllCCS[M+NH4]+233.432859911
AllCCS[M+Na]+233.432859911
AllCCS[M-H]-238.432859911
AllCCS[M+Na-2H]-241.232859911
AllCCS[M+HCOO]-244.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
P1,P4-Bis(5'-uridyl) tetraphosphateO[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O)N1C=CC(=O)NC1=O6115.7Standard polar33892256
P1,P4-Bis(5'-uridyl) tetraphosphateO[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O)N1C=CC(=O)NC1=O3695.8Standard non polar33892256
P1,P4-Bis(5'-uridyl) tetraphosphateO[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O)N1C=CC(=O)NC1=O6328.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-03k9-2305694200-945d0816923773e0eab72017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate 10V, Positive-QTOFsplash10-03di-0900000100-6b4cd5d46e30254bdbd42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate 20V, Positive-QTOFsplash10-03di-2900000000-4ef207daf511a07e7b582017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate 40V, Positive-QTOFsplash10-03di-3900000000-43866880b00421ce3a762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate 10V, Negative-QTOFsplash10-01pc-3400010900-5ca71201173b857225102017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate 20V, Negative-QTOFsplash10-01ox-9501140200-65eefe45868b08c82c9f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate 40V, Negative-QTOFsplash10-03xu-6629210100-e748c6acda0c2008fd4a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate 10V, Positive-QTOFsplash10-03di-0200009300-211fcec2c46145c8d3cb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate 20V, Positive-QTOFsplash10-03di-0300019400-de5c9ddc51e7fd34a17a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate 40V, Positive-QTOFsplash10-03di-0900300000-a17b44f6aa0bebe785ea2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate 10V, Negative-QTOFsplash10-000i-0000001900-40b1c930546295748a152021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate 20V, Negative-QTOFsplash10-03dl-1403987700-dbeb7a52ada3758ec1ad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-uridyl) tetraphosphate 40V, Negative-QTOFsplash10-0w9c-1212910300-c9a61b7208e988734b052021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024083
KNApSAcK IDNot Available
Chemspider ID130647
KEGG Compound IDC06198
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound148197
PDB IDNot Available
ChEBI ID27791
Food Biomarker OntologyNot Available
VMH IDUP4G
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Asymmetrically hydrolyzes Ap4A to yield AMP and ATP. Plays a major role in maintaining homeostasis.
Gene Name:
NUDT2
Uniprot ID:
P50583
Molecular weight:
16829.09
Reactions
P1,P4-Bis(5'-uridyl) tetraphosphate + Water → Uridine triphosphate + Uridine 5'-monophosphatedetails