Back to Compounds

Showing Compound dUTP (FDB030842)

Record Information
Version1.0
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
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility8.63 g/LALOGPS
logP-0.12ALOGPS
logP-2.5ChemAxon
logS-1.7ALOGPS
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
BioavailabilityNoChemAxon
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
InChI KeyAHCYMLUZIRLXAA-SHYZEUOFSA-N
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
Classification
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
Substituents
  • 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
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
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0100900000-8e7a148aec1d751cc1c42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-4911000000-4e7687aefa9b30fe654c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0aor-0913400000-108f05d6274de41c6fbc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-1922000000-1891134d52577ca759f02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-9000000000-192f049c7d1787f75c4c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-9000000000-57fd03e21769cf32cb692021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-1922000000-489aaa48942eed69703b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-9000000000-f4b40a8824847f5ca8a72021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-9dfd5f9811270d9aaab82015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-b480c4f463f71544be8f2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-2ba3b00121251c9adda02015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-3120900000-dedbedae66448a647f3b2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057u-9430100000-0b81cc8084e6bd0f30882015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9510000000-a72cd2e823cab077b0e12015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0003900000-eff09a2f41b2c9e593432021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9715400000-83fd98a60651b67d2aea2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9201000000-c6b0a4a5f0bb84bc19872021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2900200000-ad484f076fd7c4b32fb92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9701100000-04958af5fb614287d4a02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0910000000-52122719a1b16858a2a02021-09-24View Spectrum
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference