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Record Information
Version3.6
Creation Date2013-05-17 00:59:27 UTC
Update Date2017-03-02 22:05:01 UTC
HMDB IDHMDB60396
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Fluorouridine
Description5-Fluorouridine 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-fluoro-UridineChEBI
5-Fluorouracil 1beta-D-ribofuranosideChEBI
5-Fluorouracil 1b-D-ribofuranosideGenerator
5-Fluorouracil 1β-D-ribofuranosideGenerator
5-Fluorouridine, 18F-labeledMeSH
Chemical FormulaC9H11FN2O6
Average Molecular Weight262.1918
Monoisotopic Molecular Weight262.060114299
IUPAC Name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Name5-fluorouridine
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=C(F)C(=O)NC1=O
InChI Identifier
InChI=1S/C9H11FN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1
InChI KeyFHIDNBAQOFJWCA-UAKXSSHOSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrimidine nucleosides. These are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassNot Available
Direct ParentPyrimidine nucleosides
Alternative Parents
Substituents
  • Pyrimidine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Halopyrimidine
  • Pyrimidone
  • Aryl fluoride
  • Aryl halide
  • Hydropyrimidine
  • Monosaccharide
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Lactam
  • Urea
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locationsNot Available
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 Solubility10.7 mg/mLALOGPS
logP-1.4ALOGPS
logP-2.2ChemAxon
logS-0.64ALOGPS
pKa (Strongest Acidic)7.67ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area119.33 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.77 m3·mol-1ChemAxon
Polarizability21.9 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
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 IDNot Available
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID9056
      KEGG Compound IDC16633
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB60396
      Metagene LinkHMDB60396
      METLIN IDNot Available
      PubChem Compound9427
      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 ATP binding
      Specific function:
      Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
      Gene Name:
      UCK1
      Uniprot ID:
      Q9HA47
      Molecular weight:
      22760.43
      Reactions
      5-Fluorouridine + Adenosine triphosphate → 5-Fluorouridine monophosphate + ADPdetails
      General function:
      Involved in ATP binding
      Specific function:
      Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
      Gene Name:
      UCK2
      Uniprot ID:
      Q9BZX2
      Molecular weight:
      29298.92
      Reactions
      5-Fluorouridine + Adenosine triphosphate → 5-Fluorouridine monophosphate + ADPdetails
      General function:
      Involved in transferase activity, transferring pentosyl groups
      Specific function:
      Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1-phosphate. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
      Gene Name:
      UPP1
      Uniprot ID:
      Q16831
      Molecular weight:
      33934.005
      Reactions
      Fluorouracil + Ribose 1-phosphate → 5-Fluorouridine + Phosphoric aciddetails
      General function:
      Involved in transferase activity, transferring pentosyl groups
      Specific function:
      Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1-phosphate. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis. Shows substrate specificity and accept uridine, deoxyuridine, and thymidine as well as the two pyrimidine nucleoside analogs 5-fluorouridine and 5-fluoro-2(')-deoxyuridine as substrates.
      Gene Name:
      UPP2
      Uniprot ID:
      O95045
      Molecular weight:
      41601.795
      Reactions
      Fluorouracil + Ribose 1-phosphate → 5-Fluorouridine + Phosphoric aciddetails
      General function:
      Involved in ATP binding
      Specific function:
      May contribute to UTP accumulation needed for blast transformation and proliferation.
      Gene Name:
      UCKL1
      Uniprot ID:
      Q9NWZ5
      Molecular weight:
      59465.77
      Reactions
      5-Fluorouridine + Adenosine triphosphate → 5-Fluorouridine monophosphate + ADPdetails