Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:59:58 UTC
Update Date2023-02-21 17:29:58 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
Data?1677000598
Synonyms
ValueSource
5-FluorodihydrouracilKegg
(R)-5-Fluoro-5,6-dihydrouracilHMDB
DHFUHMDB
5,6-DihydrofluorouracilHMDB
5-DihydrofluorouracilHMDB
5-Fluorodihydrouracil, sodium saltHMDB
Chemical FormulaC4H5FN2O2
Average Molecular Weight132.0931
Monoisotopic Molecular Weight132.033505619
IUPAC Name5-fluoro-1,3-diazinane-2,4-dione
Traditional Name5,6-dihydro-5-fluorouracil
CAS Registry NumberNot Available
SMILES
FC1CNC(=O)NC1=O
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
Description Belongs to the class of organic compounds known as hydropyrimidines. Hydropyrimidines are compounds containing a hydrogenated pyrimidine ring (i.E. Containing less than the maximum number of double bonds.).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.99 g/LALOGPS
logP-1.2ALOGPS
logP-1ChemAxon
logS-0.43ALOGPS
pKa (Strongest Acidic)10.66ChemAxon
pKa (Strongest Basic)-8.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.39 m³·mol⁻¹ChemAxon
Polarizability10.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+126.82330932474
DeepCCS[M-H]-123.68930932474
DeepCCS[M-2H]-160.69130932474
DeepCCS[M+Na]+135.55330932474
AllCCS[M+H]+128.932859911
AllCCS[M+H-H2O]+124.232859911
AllCCS[M+NH4]+133.332859911
AllCCS[M+Na]+134.632859911
AllCCS[M-H]-122.032859911
AllCCS[M+Na-2H]-124.132859911
AllCCS[M+HCOO]-126.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,6-Dihydro-5-fluorouracilOC1=NCC(F)C(O)=N12184.7Standard polar33892256
5,6-Dihydro-5-fluorouracilOC1=NCC(F)C(O)=N11264.8Standard non polar33892256
5,6-Dihydro-5-fluorouracilOC1=NCC(F)C(O)=N11322.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,6-Dihydro-5-fluorouracil,1TMS,isomer #1C[Si](C)(C)OC1=NCC(F)C(O)=N11407.5Semi standard non polar33892256
5,6-Dihydro-5-fluorouracil,1TMS,isomer #2C[Si](C)(C)OC1=NC(O)=NCC1F1386.2Semi standard non polar33892256
5,6-Dihydro-5-fluorouracil,2TMS,isomer #1C[Si](C)(C)OC1=NCC(F)C(O[Si](C)(C)C)=N11389.5Semi standard non polar33892256
5,6-Dihydro-5-fluorouracil,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NCC(F)C(O)=N11578.8Semi standard non polar33892256
5,6-Dihydro-5-fluorouracil,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC(O)=NCC1F1559.8Semi standard non polar33892256
5,6-Dihydro-5-fluorouracil,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NCC(F)C(O[Si](C)(C)C(C)(C)C)=N11775.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydro-5-fluorouracil GC-MS (Non-derivatized) - 70eV, Positivesplash10-03l0-9300000000-d53f960f30e9f2726fbc2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydro-5-fluorouracil GC-MS (2 TMS) - 70eV, Positivesplash10-0hb9-9440000000-cbbf98d30b677e94205e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydro-5-fluorouracil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydro-5-fluorouracil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-fluorouracil 10V, Positive-QTOFsplash10-001i-1900000000-19ba74a08c9c824e9dc12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-fluorouracil 20V, Positive-QTOFsplash10-01q9-5900000000-71963cc6180144de73c62016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-fluorouracil 40V, Positive-QTOFsplash10-03dm-9000000000-6690c8cc65e6b42ba7ae2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-fluorouracil 10V, Positive-QTOFsplash10-001i-1900000000-19ba74a08c9c824e9dc12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-fluorouracil 20V, Positive-QTOFsplash10-01q9-5900000000-71963cc6180144de73c62016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-fluorouracil 40V, Positive-QTOFsplash10-03dm-9000000000-6690c8cc65e6b42ba7ae2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-fluorouracil 10V, Negative-QTOFsplash10-000i-9200000000-07df5cbc1566b07805902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-fluorouracil 20V, Negative-QTOFsplash10-0006-9000000000-7125b6d8f066a7df0e7e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-fluorouracil 40V, Negative-QTOFsplash10-0006-9000000000-10dcbf73803e32c7e7a72016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID108825
KEGG Compound IDC16630
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound121997
PDB IDNot Available
ChEBI ID80624
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1795471
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