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Showing Compound 5,6-dihydrouracil (FDB030556)

Record Information
Version1.0
Creation date2015-05-07 19:29:50 UTC
Update date2019-11-26 03:21:49 UTC
Primary IDFDB030556
Secondary Accession Numbers
  • FDB021890
Chemical Information
FooDB Name5,6-dihydrouracil
Description3,4-dihydrouracil, also known as 2,4-dioxotetrahydropyrimidine or 5,6-dihydro-2,4-dihydroxypyrimidine, is a member of the class of 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. 3,4-dihydrouracil is soluble (in water) and a very weakly acidic compound (based on its pKa). 3,4-dihydrouracil can be found in a number of food items such as colorado pinyon, rocket salad (sspecies), wax gourd, and boysenberry, which makes 3,4-dihydrouracil a potential biomarker for the consumption of these food products. 3,4-dihydrouracil can be found primarily in blood, cerebrospinal fluid (CSF), saliva, and urine, as well as throughout most human tissues. 3,4-dihydrouracil exists in all living organisms, ranging from bacteria to humans. In humans, 3,4-dihydrouracil is involved in a couple of metabolic pathways, which include beta-alanine metabolism and pyrimidine metabolism. 3,4-dihydrouracil is also involved in several metabolic disorders, some of which include UMP synthase deficiency (orotic aciduria), dihydropyrimidinase deficiency, ureidopropionase deficiency, and carnosinuria, carnosinemia. Moreover, 3,4-dihydrouracil is found to be associated with dihydropyrimidine dehydrogenase deficiency and hypertension.
CAS Number504-07-4
Structure
Thumb
MOLSDFPDBSMILESInChI
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
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
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
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-03fu-9400000000-5b9edda3479e7d0a0d282014-09-20View Spectrum
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
Predicted GC-MSDihydrouracil, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03k9-9800000000-da772cea603c785c1df42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9100000000-94a5f543e8c6be7b32042012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0btc-9200000000-e9bf2ae82714a2a3a7372012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-5900000000-0fe83e63f6e5d13478942012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-03xr-6900000000-08aca1bc7f27b0e7cb082017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-5900000000-53ea361c86b4f9fa284b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-9300000000-a8599c09cd21e2f843292017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01b9-9500000000-03c8b6a5b2dc3625d5d32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-331f648f78f506788b992021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-824aa91d3f2de539f0bd2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2900000000-ad7f91d5265e53403dd62015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0603-9200000000-4b30a83fb454e5bbffb82015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ce54e3c860a95b0af4012015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9800000000-d705e188f6700a76ef722015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-a26409d69a42597310042015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f00c4df547660023bee42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-b8f2cf36966bbbbb32852021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9500000000-44775319047d2eddad492021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-3cb7005ca8389854848e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-7900000000-9d78d5698ad7865d17892021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-997cffdd9ad85c8992252021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-a88e812ae86e53f6c2d62021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
FoodReference
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