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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:59:31 UTC
Update Date2017-12-07 16:53:48 UTC
HMDB IDHMDB0060397
Secondary Accession Numbers
  • HMDB60397
Metabolite Identification
Common Name5-Fluorouridine monophosphate
Description5-Fluorouridine monophosphate 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-F-UMPChEBI
5-Fluorouridine monophosphateChEBI
5-Fluorouridylic acidChEBI
FosfluoridineChEBI
Fump-5'ChEBI
5-Fluorouridine 5'-monophosphoric acidGenerator
5-Fluorouridine monophosphoric acidGenerator
5-FluorouridylateGenerator
5-Fluorouridine 5'-phosphateMeSH
5-Fluorouridine 5'-phosphate, 18F-labeledMeSH
5'-FUMPMeSH
5-Fluorouridine 5'-phosphate, disodium saltMeSH
5-Fluorouridine 5'-phosphate, calcium saltMeSH
Chemical FormulaC9H12FN2O9P
Average Molecular Weight342.1717
Monoisotopic Molecular Weight342.026444709
IUPAC Name{[(2R,3S,4R,5R)-5-(5-fluoro-4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name5-fluorouridylate
CAS Registry NumberNot Available
SMILES
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=C(F)C(O)=NC1=O
InChI Identifier
InChI=1S/C9H12FN2O9P/c10-3-1-12(9(16)11-7(3)15)8-6(14)5(13)4(21-8)2-20-22(17,18)19/h1,4-6,8,13-14H,2H2,(H,11,15,16)(H2,17,18,19)/t4-,5-,6-,8-/m1/s1
InChI KeyRNBMPPYRHNWTMA-UAKXSSHOSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleotides
Direct ParentPyrimidine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Pyrimidine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Halopyrimidine
  • Pyrimidone
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Aryl fluoride
  • Pyrimidine
  • Aryl halide
  • Phosphoric acid ester
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Urea
  • Secondary alcohol
  • 1,2-diol
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Organohalogen compound
  • Organofluoride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  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 Solubility12.4 g/LALOGPS
logP-1.4ALOGPS
logP-2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area169.35 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.96 m³·mol⁻¹ChemAxon
Polarizability26.61 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, Positivesplash10-0002-9501000000-6e3e3f07071a4b3fe25bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000b-9422320000-a9309e7224043db6e96eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0901000000-3b46c2e15a4da2f0d7baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-5e082b9fb7ff4e4a3befView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-3900000000-95bf4479fa01e01b5fd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-6932000000-83f85ee655c0c86555daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-3d9058daaa7d559c901eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4b472f80502ae0db304eView in MoNA
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID132962
      KEGG Compound IDC16634
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound150856
      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 catalytic activity
      Specific function:
      Not Available
      Gene Name:
      UMPS
      Uniprot ID:
      P11172
      Molecular weight:
      52221.075
      Reactions
      Fluorouracil + Phosphoribosyl pyrophosphate → 5-Fluorouridine monophosphate + Pyrophosphatedetails
      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 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