<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:42:20 UTC</creation_date>
  <update_date>2026-08-24 12:18:53 UTC</update_date>
  <accession/>
  <common_name>Lamivudine</common_name>
  <class>SmallMolecule</class>
  <description>Lamivudine is an organic compound with the formula C8H11N3O3S and an average molecular weight of 229.25 g/mol. Lamivudine belongs to the 3'-thia pyrimidine nucleosides, a subclass of nucleoside and nucleotide analogues within the organic compounds. It functions as an antiviral drug (PMC10054433).

The compound acts as an inhibitor or modulator of Protein P and targets the Gag-Pol polyprotein (gag-pol) as well as Reverse transcriptase/RNaseH (pol). Regarding its distribution and exposure, lamivudine is found in or released from 10 recorded sources. These include healthcare, pharmaceuticals, and veterinary products such as antivirals, as well as household cleaning and consumer products including cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Additionally, it is associated with electrical and electronic equipment, specifically antennas, coils, electrically stimulated smoking devices, radio transmission systems, television systems, and one other source. The recorded route of exposure for this compound is oral.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms>
    <synonym>4-amino-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one</synonym>
  </synonyms>
  <chemical_formula>C8H11N3O3S</chemical_formula>
  <average_molecular_weight>229.25</average_molecular_weight>
  <monisotopic_moleculate_weight>229.0521124</monisotopic_moleculate_weight>
  <iupac_name>1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-4-imino-1,4-dihydropyrimidin-2-ol</iupac_name>
  <traditional_iupac>lamivudine</traditional_iupac>
  <cas_registry_number>134678-17-4</cas_registry_number>
  <smiles>[H][C@]1(CO)O[C@]([H])(CS1)N1C=CC(=N)N=C1O</smiles>
  <inchi>InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m1/s1</inchi>
  <inchikey>JTEGQNOMFQHVDC-RQJHMYQMSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Nucleoside and nucleotide analogues</class>
    <sub_class>3'-thia pyrimidine nucleosides</sub_class>
    <direct_parent>3'-thia pyrimidine nucleosides</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>Monothioacetals</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxathiolanes</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>3'-thia pyrimidine nucleoside</substituent>
      <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>Monothioacetal</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>Oxathiolane</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</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>Lamivudine Metabolism Pathway</name>
      <smpdb_id>SMP0000649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lamivudine Action Pathway</name>
      <smpdb_id>SMP0000742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lamivudine Anti-viral Action Pathway</name>
      <smpdb_id>SMP0124937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lamivudine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143153</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.45e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-4-imino-1,4-dihydropyrimidin-2-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>229.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>229.0521124</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(CO)O[C@]([H])(CS1)N1C=CC(=N)N=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H11N3O3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JTEGQNOMFQHVDC-RQJHMYQMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>89.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>66.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</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:0x00007f726c568ac0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00709</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>60825</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>54812</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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  </targets>
</compound>
