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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:59:19 UTC
Update Date2019-07-23 07:14:14 UTC
HMDB IDHMDB0060394
Secondary Accession Numbers
  • HMDB60394
Metabolite Identification
Common Name5-Fluorodeoxyuridine monophosphate
Description5-Fluorodeoxyuridine monophosphate, also known as fdump or 5-fluorodeoxyuridylic acid, belongs to the class of organic compounds 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. 5-Fluorodeoxyuridine monophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Fluorodeoxyuridine monophosphate exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1563866054
Synonyms
ValueSource
5-Fluorodeoxyuridine monophosphoric acidGenerator
5-Fluoro-2-deoxyuridine monophosphate (fdump)HMDB
5-Fluoro-2-deoxyuridine monophosphoric acid (fdump)HMDB
5-FLUORODEOXYURIDYLic acidHMDB
5-Fluoro-2'-deoxyuridine-5'-monophosphateHMDB
5 Fluoro 2' deoxyuridine 5' monophosphateHMDB
FdUMPHMDB
FluorodeoxyuridylateMeSH
5-Fluoro-2'-deoxyuridine-5'-monophosphoric acidGenerator
Chemical FormulaC9H12FN2O8P
Average Molecular Weight326.1723
Monoisotopic Molecular Weight326.031530087
IUPAC Name{[(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3H-pyrimidin-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
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine deoxyribonucleotides
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

Source:

Biological location:

Role

Industrial application:

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 Solubility8.91 g/LALOGPS
logP-1.3ALOGPS
logP-1.4ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area145.63 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.13 m³·mol⁻¹ChemAxon
Polarizability25.94 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9410000000-870fe831cb893d234c57Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ot-8933200000-173c2e295b577396d9a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-602d1057b95d15b1b0a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-48ba814243131de9c0feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-5900000000-02ecf9c6cb7457c735eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01u3-9553000000-7cf12c8b649a0477f6f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-096c87690821f662e9fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-7d84920d2729eda0963fSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDDB03761
      Phenol Explorer Compound IDNot Available
      FooDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC04242
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound8642
      PDB IDNot Available
      ChEBI IDNot Available
      Food Biomarker OntologyNot Available
      VMH 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:
      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