<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:23:10 UTC</creation_date>
  <update_date>2026-08-22 13:44:17 UTC</update_date>
  <accession/>
  <common_name>Fosfomycin</common_name>
  <class>SmallMolecule</class>
  <description>Fosfomycin is an organic compound with the chemical formula C3H7O4P and an average molecular weight of 138.06 g/mol. Fosfomycin belongs to the organic phosphonic acids, a subclass of organic phosphonic acids and derivatives within the organic compounds. In terms of biological activity, it acts as an inhibitor of the protein target UDP-N-acetylglucosamine 1-carboxyvinyltransferase (murA).

The compound is found in or released from eight recorded sources. These include pharmaceuticals and veterinary products, specifically antibiotics, antiinfectives, and antibacterials. It is also associated with food, food processing and cookware, specifically processing meats, as well as household cleaning and consumer products, such as non electric simulated smoking devices. Additionally, it is found in electrical and electronic equipment, including television systems, antennas, and video games. Recorded exposure routes for fosfomycin include oral, intravenous, and inhalation.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C3H7O4P</chemical_formula>
  <average_molecular_weight>138.059</average_molecular_weight>
  <monisotopic_moleculate_weight>138.008195224</monisotopic_moleculate_weight>
  <iupac_name>[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid</iupac_name>
  <traditional_iupac>fosfomycin</traditional_iupac>
  <cas_registry_number>23155-02-4</cas_registry_number>
  <smiles>C[C@@H]1O[C@@H]1P(O)(O)=O</smiles>
  <inchi>InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1</inchi>
  <inchikey>YMDXZJFXQJVXBF-STHAYSLISA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphonic acids and derivatives</class>
    <sub_class>Organic phosphonic acids</sub_class>
    <direct_parent>Organic phosphonic acids</direct_parent>
    <alternate_parents>
      <alternative_parent>Epoxides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organophosphorus compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organophosphonic acid</substituent>
      <substituent>Organophosphorus compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxirane</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Aliphatic compounds</descriptor>
      <descriptor>epoxide</descriptor>
      <descriptor>phosphonic acids</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Fosfomycin Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143266</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-0.74</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.69e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>138.059</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>138.008195224</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H]1O[C@@H]1P(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7O4P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YMDXZJFXQJVXBF-STHAYSLISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>70.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</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/>
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  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7227ab7778&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00828</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>446987</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>394204</chemspider_id>
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