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Record Information
Version3.6
Creation Date2013-05-17 00:59:19 UTC
Update Date2016-02-11 08:04:58 UTC
HMDB IDHMDB60394
Secondary Accession NumbersNone
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
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=1/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+/s2
InChI KeyInChIKey=HFEKDTCAMMOLQP-YUZWJPFSNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrimidine deoxyribonucleotides. These are pyrimidine nucleotides where the purine moiety is linked to a ribose lacking a hydroxyl group at one or more positions.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine deoxyribonucleotides
Direct ParentPyrimidine deoxyribonucleotides
Alternative Parents
Substituents
  • Pyrimidine deoxyribonucleotide
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Halopyrimidine
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydropyrimidine
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Oxolane
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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 Solubility8.91 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.45 m3·mol-1ChemAxon
Polarizability25.42 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB60394
Metagene LinkHMDB60394
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, Consortium U: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [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