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Record Information
Version1.0
Creation Date2016-07-13 19:40:54 UTC
Update Date2016-07-20 20:54:37 UTC
LmdbLMDB00033
Secondary Accession NumbersNone
Metabolite Identification
Common NameDihydrouracil
DescriptionDihydrouracil belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Dihydrouracil is an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydrouracil exists in all living organisms, ranging from bacteria to humans. Within humans, dihydrouracil participates in a number of enzymatic reactions. In particular, dihydrouracil can be biosynthesized from uracil; which is mediated by the enzyme dihydropyrimidine dehydrogenase [nadp(+)]. In addition, dihydrouracil can be converted into ureidopropionic acid; which is mediated by the enzyme dihydropyrimidinase. In humans, dihydrouracil is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. Outside of the human body, Dihydrouracil has been detected, but not quantified in, several different foods, such as arctic blackberries, garden tomato (var.), sweet potato, star fruits, and adzuki beans. This could make dihydrouracil a potential biomarker for the consumption of these foods. Dihydrouracil is a potentially toxic compound. Dihydrouracil, with regard to humans, has been found to be associated with several diseases such as cerebral infarction, liver disease, colorectal cancer, and hypertension; dihydrouracil has also been linked to the inborn metabolic disorder dihydropyrimidine dehydrogenase deficiency. A pyrimidine obtained by formal addition of hydrogen across the 5,6-position of uracil.
Structure
Thumb
Synonyms
ValueSource
2,4-DioxotetrahydropyrimidineChEBI
5,6-Dihydro-2,4-dihydroxypyrimidineChEBI
Dihydro-2,4(1H,3H)-pyrimidinedioneChEBI
DIHYDROPYRIMIDINE-2,4(1H,3H)-dioneChEBI
DihydrouracileChEBI
HydrouracilChEBI
5,6-Dihydro-2,4(1H,3H)-pyrimidinedioneHMDB
5,6-DihydrouracilHMDB
Dihydro-pyrimidine-2,4-dioneHMDB
Chemical FormulaC4H6N2O2
Average Molecular Weight114.1026
Monoisotopic Molecular Weight114.042927446
IUPAC Name1,3-diazinane-2,4-dione
Traditional Namedihydrouracil
CAS Registry Number504-07-4
SMILES
O=C1CCNC(=O)N1
InChI Identifier
InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)
InChI KeyOIVLITBTBDPEFK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidones
Alternative Parents
Substituents
  • N-acyl urea
  • Pyrimidone
  • Ureide
  • 1,3-diazinane
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Azacycle
  • Carboxylic acid derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.3ALOGPS
logP-1.2ChemAxon
logS-0.64ALOGPS
pKa (Strongest Acidic)11.73ChemAxon
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.75 m³·mol⁻¹ChemAxon
Polarizability10.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9700000000-4adeeb2f4f5a1111afb7Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00di-5900000000-8af1b81502646fa5b417Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0fdo-9750000000-d2aaeeba1cf962175f84Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9700000000-4adeeb2f4f5a1111afb7Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-5900000000-8af1b81502646fa5b417Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fdo-9750000000-d2aaeeba1cf962175f84Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6w-2940000000-3430a0e2d1819021af1dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-3900000000-79f2d90a419b7469cb61Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9100000000-55536f0571922b6c69feSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03k9-9800000000-da772cea603c785c1df4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9100000000-94a5f543e8c6be7b3204Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0btc-9200000000-e9bf2ae82714a2a3a737Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-5900000000-0fe83e63f6e5d1347894Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03xr-6900000000-08aca1bc7f27b0e7cb08Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-5900000000-53ea361c86b4f9fa284bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-9300000000-a8599c09cd21e2f84329Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01b9-9500000000-03c8b6a5b2dc3625d5d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-331f648f78f506788b99Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-824aa91d3f2de539f0bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2900000000-ad7f91d5265e53403dd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0603-9200000000-4b30a83fb454e5bbffb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ce54e3c860a95b0af401Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9800000000-d705e188f6700a76ef72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-a26409d69a4259731004Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f00c4df547660023bee4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-b8f2cf36966bbbbb3285Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9500000000-44775319047d2eddad49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-3cb7005ca8389854848eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-7900000000-9d78d5698ad7865d1789Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-997cffdd9ad85c899225Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-a88e812ae86e53f6c2d6Spectrum
MSMass Spectrum (Electron Ionization)splash10-03fu-9400000000-5b9edda3479e7d0a0d28Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDDB01849
HMDB IDHMDB0000076
FooDB IDFDB030556
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID34956
BioCyc IDDI-H-URACIL
METLIN ID285
PDB IDNot Available
Wikipedia LinkDihydrouracil
Chemspider ID629
ChEBI ID15901
PubChem Compound ID649
Kegg Compound IDC00429
YMDB IDNot Available
ECMDB IDECMDB00076
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available