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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:00:20 UTC
Update Date2017-10-23 19:15:42 UTC
HMDB IDHMDB0060406
Secondary Accession Numbers
  • HMDB60406
Metabolite Identification
Common Name5'-Deoxy-5-fluorouridine
Description5'-Deoxy-5-fluorouridine is a metabolite of capecitabine. Capecitabine (Xeloda, Roche) is an orally-administered chemotherapeutic agent used in the treatment of metastatic breast and colorectal cancers. Capecitabine is a prodrug, that is enzymatically converted to 5-fluorouracil in the tumor, where it inhibits DNA synthesis and slows growth of tumor tissue. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
1-(beta-D-5-Desoxyribofuranoxyl)-5-fluoruracilChEBI
5'-DFURChEBI
5'-DFUrdChEBI
5-fluoro-5'-DeoxyuridineChEBI
DoxifluridinaChEBI
DoxifluridinumChEBI
FurtulonChEBI
ro 21-9738ChEBI
ro 219738ChEBI
1-(b-D-5-Desoxyribofuranoxyl)-5-fluoruracilGenerator
1-(β-D-5-desoxyribofuranoxyl)-5-fluoruracilGenerator
5'-Deoxy-5'-fluorouridineMeSH
5'-Deoxy-5-fluorouridineMeSH
5'-fluoro-5'-DeoxyuridineMeSH
DoxyfluridineMeSH
Chemical FormulaC9H11FN2O5
Average Molecular Weight246.1924
Monoisotopic Molecular Weight246.065199677
IUPAC Name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-4-hydroxy-1,2-dihydropyrimidin-2-one
Traditional Namedoxifluridine
CAS Registry NumberNot Available
SMILES
C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=C(F)C(O)=NC1=O
InChI Identifier
InChI=1S/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6-,8-/m1/s1
InChI KeyZWAOHEXOSAUJHY-ZIYNGMLESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 5'-deoxyribonucleosides. These are nucleosides in which the oxygen atom at the 5'position of the ribose moiety has been replaced by another atom. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub Class5'-deoxyribonucleosides
Direct Parent5'-deoxyribonucleosides
Alternative Parents
Substituents
  • 5'-deoxyribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Halopyrimidine
  • Pyrimidone
  • Aryl fluoride
  • Aryl halide
  • Pyrimidine
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Urea
  • Secondary alcohol
  • 1,2-diol
  • Lactam
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Industrial application:

  Pharmaceutical industry:

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 Solubility5.36 g/LALOGPS
logP-0.82ALOGPS
logP-0.8ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)6.2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area102.59 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.55 m³·mol⁻¹ChemAxon
Polarizability21.06 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-056u-9210000000-68ddd4a6bcf1d8ff7c3fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00tk-6976700000-d826a815dab6401bbc3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0910000000-7e78eab45706c44d825fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-17e125f0d2b5d65e776eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-9400000000-4647ffbb75476b52110aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004l-5950000000-62edf53c23a7fcae3ddeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4930000000-e1442f1a62dab8ca8e79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-583eee0dde55403044a4View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Capecitabine Metabolism PathwayPw000583Pw000583 greyscalePw000583 simpleNot Available
Capecitabine PathwayPw000256Pw000256 greyscalePw000256 simpleNot Available
Displaying all 2 entries
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 IDDBMET00656
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID17322
      KEGG Compound IDC12739
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound18343
      PDB IDNot Available
      ChEBI ID269379
      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 transferase activity, transferring glycosyl groups
      Specific function:
      May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in vitro. Catalyzes the reversible phosphorolysis of thymidine. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
      Gene Name:
      TYMP
      Uniprot ID:
      P19971
      Molecular weight:
      49954.965
      Reactions
      5'-Deoxy-5-fluorouridine + Phosphoric acid → Fluorouracil + 5-Deoxyribose-1-phosphatedetails
      General function:
      Involved in zinc ion binding
      Specific function:
      This enzyme scavenge exogenous and endogenous cytidine and 2'-deoxycytidine for UMP synthesis.
      Gene Name:
      CDA
      Uniprot ID:
      P32320
      Molecular weight:
      16184.545
      Reactions
      5'-Deoxy-5-fluorocytidine + Water → 5'-Deoxy-5-fluorouridine + Ammoniadetails