<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:41:13 UTC</creation_date>
  <update_date>2026-05-14 16:25:24 UTC</update_date>
  <accession/>
  <common_name>Floxuridine</common_name>
  <class>SmallMolecule</class>
  <description>Floxuridine is an organic compound with the chemical formula C9H11FN2O5 and an average molecular weight of 246.19 g/mol. Floxuridine belongs to the pyrimidine 2'-deoxyribonucleosides, a subclass of pyrimidine nucleosides within the organic compounds. Within the biological system, it acts on two recorded protein targets, serving as an inhibitor of Thymidylate synthase (TYMS) and targeting Thymidylate synthase (TMP1).

The compound is documented in seven recorded sources. In the realm of healthcare, pharmaceuticals, and veterinary products, it is used as an antineoplastic agent. Other recorded sources include food, food processing, and cookware, specifically regarding food preservation and fermentation processes for beer. It is also associated with household cleaning and consumer products, such as tobacco smoke filters and perfumes within detergents and soaps. Additionally, it is found in electrical and electronic equipment, specifically electrically stimulated smoking devices and conductive bodies characterized by conductive materials. The recorded route of exposure for this compound is intra-arterial.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C9H11FN2O5</chemical_formula>
  <average_molecular_weight>246.1924</average_molecular_weight>
  <monisotopic_moleculate_weight>246.065199677</monisotopic_moleculate_weight>
  <iupac_name>5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione</iupac_name>
  <traditional_iupac>floxuridine</traditional_iupac>
  <cas_registry_number>50-91-9</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(F)C(=O)NC1=O</smiles>
  <inchi>InChI=1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1</inchi>
  <inchikey>ODKNJVUHOIMIIZ-RRKCRQDMSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleosides</class>
    <sub_class>Pyrimidine 2'-deoxyribonucleosides</sub_class>
    <direct_parent>Pyrimidine 2'-deoxyribonucleosides</direct_parent>
    <alternate_parents>
      <alternative_parent>Aryl fluorides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Halopyrimidines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organofluorides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aryl fluoride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Halopyrimidine</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organofluoride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>nucleoside analogue</descriptor>
      <descriptor>organofluorine compound</descriptor>
      <descriptor>pyrimidine 2'-deoxyribonucleoside</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Fluorouracil Metabolism</name>
      <smpdb_id>SMP0121111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fluorouracil Pyrimidine Analog Action Pathway</name>
      <smpdb_id>SMP0122702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Capecitabine Action Pathway (New)</name>
      <smpdb_id>SMP0125031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Floxuridine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142781</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-1.3</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.08e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>246.1924</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>246.065199677</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(F)C(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11FN2O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ODKNJVUHOIMIIZ-RRKCRQDMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>99.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f722642ca80&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00322</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>5790</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>5586</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000324</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000021</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
  </targets>
</compound>
