Record Information
Creation date2015-05-07 20:15:52 UTC
Update date2019-11-26 03:21:54 UTC
Primary IDFDB030842
Secondary Accession Numbers
  • FDB022478
Chemical Information
FooDB NamedUTP
DescriptionDutp, also known as 2'-deoxyuridine 5'-triphosphate or deoxy-utp, is a member of the class of compounds known as pyrimidine 2'-deoxyribonucleoside triphosphates. Pyrimidine 2'-deoxyribonucleoside triphosphates are pyrimidine nucleotides with a triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. Dutp is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Dutp can be found in a number of food items such as bilberry, japanese chestnut, black radish, and lovage, which makes dutp a potential biomarker for the consumption of these food products. Dutp can be found primarily in prostate Tissue, as well as throughout most human tissues. Dutp exists in all living species, ranging from bacteria to humans. In humans, dutp is involved in the pyrimidine metabolism. Dutp is also involved in few metabolic disorders, which include beta ureidopropionase deficiency, dihydropyrimidinase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), and UMP synthase deficiency (orotic aciduria). Moreover, dutp is found to be associated with prostate cancer. Dutp is a non-carcinogenic (not listed by IARC) potentially toxic compound. Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure (T3DB).
CAS Number1173-82-6
2'-Deoxyuridine 5'-triphosphateChEBI
2'-Deoxyuridine 5'-triphosphoric acidGenerator
Deoxyuridine triphosphoric acidGenerator
2'-Deoxyuridine-5'-triphosphoric acidHMDB
2'-Deoxyuridine-5'-triphosphoric acid = dUTPHMDB
2'-Deoxyuridine 5'-(tetrahydrogen triphosphate)HMDB
2’-Deoxyuridine 5’-(tetrahydrogen triphosphate)HMDB
2’-Deoxyuridine 5’-triphosphateHMDB
Deoxyuridine 5'-triphosphateHMDB
Deoxyuridine 5’-triphosphateHMDB
Deoxyuridine triphosphateHMDB
Predicted Properties
Water Solubility8.63 g/LALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area238.69 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity83.67 m³·mol⁻¹ChemAxon
Polarizability34.62 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H15N2O14P3
IUPAC name({[({[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
InChI IdentifierInChI=1S/C9H15N2O14P3/c12-5-3-8(11-2-1-7(13)10-9(11)14)23-6(5)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,20,21)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
Isomeric SMILESO[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
Average Molecular Weight468.1417
Monoisotopic Molecular Weight467.973612734
Description Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside triphosphates. These are pyrimidine nucleotides with a triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine deoxyribonucleotides
Direct ParentPyrimidine 2'-deoxyribonucleoside triphosphates
Alternative Parents
  • Pyrimidine 2'-deoxyribonucleoside triphosphate
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydroxypyrimidine
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
TypeDescriptionSplash KeyView
Predicted GC-MSDeoxyuridine triphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4j-8963100000-15f9b7594aa45581dcc0Spectrum
Predicted GC-MSDeoxyuridine triphosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05be-9551020000-12e307f13199997c5947Spectrum
Predicted GC-MSDeoxyuridine triphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0100900000-8e7a148aec1d751cc1c4Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-4911000000-4e7687aefa9b30fe654cSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0aor-0913400000-108f05d6274de41c6fbcSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-1922000000-1891134d52577ca759f0Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-9000000000-192f049c7d1787f75c4cSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-9000000000-57fd03e21769cf32cb69Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-1922000000-489aaa48942eed69703bSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-9000000000-f4b40a8824847f5ca8a7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-9dfd5f9811270d9aaab8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-b480c4f463f71544be8fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-2ba3b00121251c9adda0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-3120900000-dedbedae66448a647f3bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057u-9430100000-0b81cc8084e6bd0f3088Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9510000000-a72cd2e823cab077b0e1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0003900000-eff09a2f41b2c9e59343Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9715400000-83fd98a60651b67d2aeaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9201000000-c6b0a4a5f0bb84bc1987Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2900200000-ad484f076fd7c4b32fb9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9701100000-04958af5fb614287d4a0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0910000000-52122719a1b16858a2a0Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference