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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:59:58 UTC
Update Date2017-12-07 16:54:11 UTC
HMDB IDHMDB0060402
Secondary Accession Numbers
  • HMDB60402
Metabolite Identification
Common Name5,6-Dihydro-5-fluorouracil
Description5,6-Dihydro-5-fluorouracil is a metabolite of fluorouracil. Fluorouracil (5-FU or f5U) (sold under the brand names Adrucil, Carac, Efudix, Efudex and Fluoroplex) is a drug that is a pyrimidine analog which is used in the treatment of cancer. It is a suicide inhibitor and works through irreversible inhibition of thymidylate synthase. It belongs to the family of drugs called antimetabolites. It is typically administered with leucovorin. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
5-FluorodihydrouracilKegg
(R)-5-fluoro-5,6-DihydrouracilMeSH
DHFUMeSH
5,6-DihydrofluorouracilMeSH
5-DihydrofluorouracilMeSH
5-Fluorodihydrouracil, sodium saltMeSH
Chemical FormulaC4H5FN2O2
Average Molecular Weight132.0931
Monoisotopic Molecular Weight132.033505619
IUPAC Name5-fluoro-5,6-dihydropyrimidine-2,4-diol
Traditional Name5-fluorodihydrouracil
CAS Registry NumberNot Available
SMILES
OC1=NCC(F)C(O)=N1
InChI Identifier
InChI=1S/C4H5FN2O2/c5-2-1-6-4(9)7-3(2)8/h2H,1H2,(H2,6,7,8,9)
InChI KeyRAIRJKWTBBDDAR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydropyrimidines. These are compounds containing a hydrogenated pyrimidine ring (i.e. containing less than the maximum number of double bonds.).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDiazines
Direct ParentHydropyrimidines
Alternative Parents
Substituents
  • Hydropyrimidine
  • 5,6-dihydropyrimidine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alkyl halide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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
Water Solubility1.99 g/LALOGPS
logP-0.71ALOGPS
logP0.22ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.25ChemAxon
pKa (Strongest Basic)1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.18 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.43 m³·mol⁻¹ChemAxon
Polarizability10.29 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03l0-9300000000-d53f960f30e9f2726fbcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0hb9-9440000000-cbbf98d30b677e94205eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1900000000-19ba74a08c9c824e9dc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-5900000000-71963cc6180144de73c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-9000000000-6690c8cc65e6b42ba7aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1900000000-19ba74a08c9c824e9dc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-5900000000-71963cc6180144de73c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-9000000000-6690c8cc65e6b42ba7aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9200000000-07df5cbc1566b0780590View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-7125b6d8f066a7df0e7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-10dcbf73803e32c7e7a7View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00655
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16630
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound0
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

      Enzymes

      General function:
      Involved in hydrolase activity
      Specific function:
      Catalyzes the second step of the reductive pyrimidine degradation, the reversible hydrolytic ring opening of dihydropyrimidines. Can catalyze the ring opening of 5,6-dihydrouracil to N-carbamyl-alanine and of 5,6-dihydrothymine to N-carbamyl-amino isobutyrate.
      Gene Name:
      DPYS
      Uniprot ID:
      Q14117
      Molecular weight:
      56629.36
      Reactions
      5,6-Dihydro-5-fluorouracil + Water → alpha-Fluoro-beta-ureidopropionic aciddetails
      General function:
      Involved in electron carrier activity
      Specific function:
      Involved in pyrimidine base degradation. Catalyzes the reduction of uracil and thymine. Also involved the degradation of the chemotherapeutic drug 5-fluorouracil.
      Gene Name:
      DPYD
      Uniprot ID:
      Q12882
      Molecular weight:
      111400.32
      Reactions
      Fluorouracil + NADPH + Hydrogen Ion → 5,6-Dihydro-5-fluorouracil + NADPdetails