Record Information
Version1.0
Creation date2011-09-21 00:04:38 UTC
Update date2020-09-17 15:38:16 UTC
Primary IDFDB021890
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number504-07-4
Structure
Thumb
Synonyms
SynonymSource
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
Dihydrouracilhmdb
Predicted Properties
PropertyValueSource
Water Solubility25.9 g/LALOGPS
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
Chemical FormulaC4H6N2O2
IUPAC name1,3-diazinane-2,4-dione
InChI IdentifierInChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)
InChI KeyOIVLITBTBDPEFK-UHFFFAOYSA-N
Isomeric SMILESO=C1CCNC(=O)N1
Average Molecular Weight114.1026
Monoisotopic Molecular Weight114.042927446
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
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
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-03fu-9400000000-5b9edda3479e7d0a0d28Spectrum
GC-MSDihydrouracil, 2 TMS, GC-MS Spectrumsplash10-00di-9700000000-4adeeb2f4f5a1111afb7Spectrum
GC-MSDihydrouracil, 1 TMS, GC-MS Spectrumsplash10-00di-5900000000-8af1b81502646fa5b417Spectrum
GC-MSDihydrouracil, 2 TMS, GC-MS Spectrumsplash10-0fdo-9750000000-d2aaeeba1cf962175f84Spectrum
GC-MSDihydrouracil, non-derivatized, GC-MS Spectrumsplash10-00di-9700000000-4adeeb2f4f5a1111afb7Spectrum
GC-MSDihydrouracil, non-derivatized, GC-MS Spectrumsplash10-00di-5900000000-8af1b81502646fa5b417Spectrum
GC-MSDihydrouracil, non-derivatized, GC-MS Spectrumsplash10-0fdo-9750000000-d2aaeeba1cf962175f84Spectrum
GC-MSDihydrouracil, non-derivatized, GC-MS Spectrumsplash10-0f6w-2940000000-3430a0e2d1819021af1dSpectrum
GC-MSDihydrouracil, non-derivatized, GC-MS Spectrumsplash10-00di-3900000000-79f2d90a419b7469cb61Spectrum
Predicted GC-MSDihydrouracil, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004l-9100000000-55536f0571922b6c69feSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03k9-9800000000-da772cea603c785c1df4Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9100000000-94a5f543e8c6be7b3204Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0btc-9200000000-e9bf2ae82714a2a3a737Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-5900000000-0fe83e63f6e5d1347894Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-03xr-6900000000-08aca1bc7f27b0e7cb08Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-5900000000-53ea361c86b4f9fa284bSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-9300000000-a8599c09cd21e2f84329Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2900000000-ad7f91d5265e53403dd6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0603-9200000000-4b30a83fb454e5bbffb8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ce54e3c860a95b0af401Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9800000000-d705e188f6700a76ef72Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-a26409d69a4259731004Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f00c4df547660023bee4Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID629
ChEMBL IDNot Available
KEGG Compound IDC00429
Pubchem Compound ID649
Pubchem Substance IDNot Available
ChEBI ID15901
Phenol-Explorer IDNot Available
DrugBank IDDB01849
HMDB IDHMDB00076
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34956
KNApSAcK IDNot Available
HET IDDUC
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Beta-Alanine MetabolismSMP00007 map00410
Pyrimidine MetabolismSMP00046 map00240
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference