<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:39:24 UTC</creation_date>
  <update_date>2026-08-22 13:22:33 UTC</update_date>
  <accession/>
  <common_name>Cycloserine</common_name>
  <class>SmallMolecule</class>
  <description>Cycloserine is an organic compound with the chemical formula C3H6N2O2 and an average molecular weight of 102.09 g/mol. Cycloserine belongs to the isoxazolines, a subclass of azolines within the organic compounds. This substance is categorized under the superclass of organoheterocyclic compounds.

The compound is found in or released from three recorded sources: amplifiers within electrical and electronic equipment, and antibiotics used as drugs for the treatment of tuberculosis within healthcare, pharmaceuticals, and veterinary products. Recorded exposure routes for this compound include oral and inhalation. In terms of biological activity, cycloserine acts on three recorded protein targets. It serves as an inhibitor of D-alanine--D-alanine ligase A (ddlA), Alanine racemase (alr), and Glutamate receptor ionotropic, NMDA 1 (GRIN1).</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>DCS</synonym>
  </synonyms>
  <chemical_formula>C3H6N2O2</chemical_formula>
  <average_molecular_weight>102.0919</average_molecular_weight>
  <monisotopic_moleculate_weight>102.042927446</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-amino-1,2-oxazolidin-3-one</iupac_name>
  <traditional_iupac>cycloserine</traditional_iupac>
  <cas_registry_number>68-41-7</cas_registry_number>
  <smiles>N[C@@H]1CONC1=O</smiles>
  <inchi>InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1</inchi>
  <inchikey>DYDCUQKUCUHJBH-UWTATZPHSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Azolines</class>
    <sub_class>Isoxazolines</sub_class>
    <direct_parent>Isoxazolines</direct_parent>
    <alternate_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoxazoline</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>4-amino-1,2-oxazolidin-3-one</descriptor>
      <descriptor>Non-ribosomal peptide/polyketide hybrids</descriptor>
      <descriptor>Non-ribosomal peptide/polyketide hybrids</descriptor>
      <descriptor>organonitrogen heterocyclic antibiotic</descriptor>
      <descriptor>organooxygen heterocyclic antibiotic</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Cycloserine Drug Metabolism</name>
      <smpdb_id>SMP0130554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cycloserine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142721</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>-1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.19e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-amino-1,2-oxazolidin-3-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>102.0919</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>102.042927446</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H]1CONC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H6N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DYDCUQKUCUHJBH-UWTATZPHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>64.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>21.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</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:0x00007f3bf33cf1f0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00260</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>51670069</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>5998</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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</compound>
