<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:41:25 UTC</creation_date>
  <update_date>2026-08-24 15:07:10 UTC</update_date>
  <accession/>
  <common_name>Cidofovir</common_name>
  <class>SmallMolecule</class>
  <description>Cidofovir is an organic compound with the formula C8H14N3O6P and an average molecular weight of 279.19 g/mol. Cidofovir belongs to the pyrimidines and pyrimidine derivatives, a subclass of diazines within the organic compounds. It is classified as an organoheterocyclic compound.

The substance is found in or released from healthcare, pharmaceuticals, and veterinary products as an antiviral. The recorded exposure route for this compound is intravenous. Regarding its biological activity, Cidofovir has two recorded protein targets: the DNA polymerase catalytic subunit and the DNA polymerase catalytic subunit (UL54), for which it acts as an inhibitor or modulator.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C8H14N3O6P</chemical_formula>
  <average_molecular_weight>279.187</average_molecular_weight>
  <monisotopic_moleculate_weight>279.062021707</monisotopic_moleculate_weight>
  <iupac_name>({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid</iupac_name>
  <traditional_iupac>cidofovir</traditional_iupac>
  <cas_registry_number>113852-37-2</cas_registry_number>
  <smiles>NC1=NC(=O)N(C[C@@H](CO)OCP(O)(O)=O)C=C1</smiles>
  <inchi>InChI=1S/C8H14N3O6P/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16)/t6-/m0/s1</inchi>
  <inchikey>VWFCHDSQECPREK-LURJTMIESA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Pyrimidones</direct_parent>
    <alternate_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <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>Imidolactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic phosphonic acids</alternative_parent>
      <alternative_parent>Organophosphorus compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organophosphonic acid</substituent>
      <substituent>Organophosphonic acid derivative</substituent>
      <substituent>Organophosphorus compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidone</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>phosphonic acids</descriptor>
      <descriptor>pyrimidone</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Cidofovir Action Pathway</name>
      <smpdb_id>SMP0125884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Brincidofovir Action Pathway</name>
      <smpdb_id>SMP0125890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cidofovir Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142827</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.15e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>279.187</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>279.062021707</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)N(C[C@@H](CO)OCP(O)(O)=O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H14N3O6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H14N3O6P/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16)/t6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VWFCHDSQECPREK-LURJTMIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>145.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</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:0x00007f722411baf0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00369</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>466146</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>409759</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>
      <target_id>BE0000343</target_id>
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    <target>
      <target_id>BE0000308</target_id>
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  </targets>
</compound>
