<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 05:24:14 UTC</creation_date>
  <update_date>2026-05-14 19:33:15 UTC</update_date>
  <accession/>
  <common_name>Edoxudine</common_name>
  <class>SmallMolecule</class>
  <description>Edoxudine is an organic compound with the chemical formula C11H16N2O5 and an average molecular weight of 256.26 g/mol. Edoxudine belongs to the pyrimidine 2'-deoxyribonucleosides, a subclass of pyrimidine nucleosides within the organic compounds.

This compound is associated with four recorded sources, including healthcare, pharmaceuticals and veterinary products where it is used as a chemotherapeutic agent. It is also found in television systems and video games categorized under electrical and electronic equipment, as well as non-electric simulated smoking devices categorized under household cleaning and consumer products. The recorded route of exposure for this substance is topical. In terms of biological activity, edoxudine interacts with two recorded protein targets, acting as an inhibitor of DNA polymerase (DNApol) and thymidine kinase, cytosolic (TK1).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C11H16N2O5</chemical_formula>
  <average_molecular_weight>256.258</average_molecular_weight>
  <monisotopic_moleculate_weight>256.105921623</monisotopic_moleculate_weight>
  <iupac_name>5-ethyl-4-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one</iupac_name>
  <traditional_iupac>β-5-ethyl-2'-deoxyuridine</traditional_iupac>
  <cas_registry_number>15176-29-1</cas_registry_number>
  <smiles>[H][C@]1(O)C[C@@]([H])(O[C@]1([H])CO)N1C=C(CC)C(O)=NC1=O</smiles>
  <inchi>InChI=1S/C11H16N2O5/c1-2-6-4-13(11(17)12-10(6)16)9-3-7(15)8(5-14)18-9/h4,7-9,14-15H,2-3,5H2,1H3,(H,12,16,17)/t7-,8+,9+/m0/s1</inchi>
  <inchikey>XACKNLSZYYIACO-DJLDLDEBSA-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>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</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>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen 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>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Edoxudine Action Pathway</name>
      <smpdb_id>SMP0125881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Edoxudine Drug Metabolism</name>
      <smpdb_id>SMP0130750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Edoxudine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0144984</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-0.67</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.06e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-ethyl-4-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>256.258</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>256.105921623</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(O)C[C@@]([H])(O[C@]1([H])CO)N1C=C(CC)C(O)=NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H16N2O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H16N2O5/c1-2-6-4-13(11(17)12-10(6)16)9-3-7(15)8(5-14)18-9/h4,7-9,14-15H,2-3,5H2,1H3,(H,12,16,17)/t7-,8+,9+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XACKNLSZYYIACO-DJLDLDEBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>102.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</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:0x00007f72a02bf3d0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB13421</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>66377</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>59752</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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      <target_id>BE0009350</target_id>
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      <target_id>BE0001260</target_id>
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  </targets>
</compound>
