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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:59:19 UTC
Update Date2017-12-07 16:53:36 UTC
HMDB IDHMDB0060394
Secondary Accession Numbers
  • HMDB60394
Metabolite Identification
Common Name5-Fluorodeoxyuridine monophosphate
Description5-Fluorodeoxyuridine monophosphate is a metabolite of floxuridine. Floxuridine (also 5-fluorodeoxyuridine) is an oncology drug that belongs to the class known as antimetabolites. The drug is most often used in the treatment of colorectal cancer. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
5-fluoro-2-Deoxyuridine monophosphate (fdump)ChEMBL
5-fluoro-2-Deoxyuridine monophosphoric acid (fdump)Generator
5-FLUORODEOXYURIDYLic acidGenerator
5-fluoro-2'-Deoxyuridine-5'-monophosphateMeSH
5 fluoro 2' Deoxyuridine 5' monophosphateMeSH
FdUMPMeSH
Chemical FormulaC9H12FN2O8P
Average Molecular Weight326.1723
Monoisotopic Molecular Weight326.031530087
IUPAC Name{[(2R,3S,5R)-5-(5-fluoro-4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,5R)-5-(5-fluoro-4-hydroxy-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=C(F)C(O)=NC1=O
InChI Identifier
InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
InChI KeyHFEKDTCAMMOLQP-RRKCRQDMSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pyrimidine 2'-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleotides
Direct ParentPyrimidine 2'-deoxyribonucleoside monophosphates
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside monophosphate
  • Halopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Aryl fluoride
  • Aryl halide
  • Hydropyrimidine
  • Pyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Urea
  • Lactam
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organofluoride
  • Alcohol
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
  • pyrimidine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:2129 )
Ontology
Disposition

Biological Location:

  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 Solubility8.91 g/LALOGPS
logP-1.2ALOGPS
logP-1.1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area149.12 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.45 m³·mol⁻¹ChemAxon
Polarizability25.42 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, Positivesplash10-0002-9410000000-870fe831cb893d234c57View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ot-8933200000-173c2e295b577396d9a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-602d1057b95d15b1b0a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-48ba814243131de9c0feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-5900000000-02ecf9c6cb7457c735eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01u3-9553000000-7cf12c8b649a0477f6f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-096c87690821f662e9fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-7d84920d2729eda0963fView 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 ID8321
      KEGG Compound IDC04242
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound8642
      PDB IDNot Available
      ChEBI ID175577
      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:
      Nucleotide transport and metabolism
      Specific function:
      Not Available
      Gene Name:
      TK1
      Uniprot ID:
      P04183
      Molecular weight:
      25468.455
      Reactions
      Floxuridine + Adenosine triphosphate → 5-Fluorodeoxyuridine monophosphate + ADPdetails
      General function:
      Involved in ATP binding
      Specific function:
      Deoxyribonucleoside kinase that phosphorylates thymidine, deoxycytidine, and deoxyuridine. Also phosphorylates anti-viral and anti-cancer nucleoside analogs.
      Gene Name:
      TK2
      Uniprot ID:
      O00142
      Molecular weight:
      27561.495
      Reactions
      Floxuridine + Adenosine triphosphate → 5-Fluorodeoxyuridine monophosphate + ADPdetails