<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 07:30:13 UTC</creation_date>
  <update_date>2026-04-05 14:18:22 UTC</update_date>
  <accession/>
  <common_name>(+/-)-cis-Permethrin</common_name>
  <class>SmallMolecule</class>
  <description>(+/-)-cis-Permethrin is an organic compound with the formula C21H20Cl2O3 and an average molecular weight of 391.29 g/mol. (+/-)-cis-Permethrin belongs to the fatty acid esters, a subclass of fatty acyls within the organic compounds. Industrially, the compound is utilized as a biocide and a pyrethroid insecticide (PMC9487696).

Regarding environmental presence and human exposure, (+/-)-cis-Permethrin is recorded in indoor air, dust, and atmospheric transport. Inhalation is a recorded exposure route, a finding supported by literature (PMC3447599).</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C21H20Cl2O3</chemical_formula>
  <average_molecular_weight>391.29</average_molecular_weight>
  <monisotopic_moleculate_weight>390.0789499</monisotopic_moleculate_weight>
  <iupac_name>(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate</iupac_name>
  <traditional_iupac>acticin</traditional_iupac>
  <cas_registry_number>61949-76-6</cas_registry_number>
  <smiles>[H][C@]1(C=C(Cl)Cl)[C@@]([H])(C(=O)OCC2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C</smiles>
  <inchi>InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3/t17-,19-/m0/s1</inchi>
  <inchikey>RLLPVAHGXHCWKJ-HKUYNNGSSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Pyrethroids</direct_parent>
    <alternate_parents>
      <alternative_parent>Benzyloxycarbonyls</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Chloroalkenes</alternative_parent>
      <alternative_parent>Cyclopropanecarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Diarylethers</alternative_parent>
      <alternative_parent>Diphenylethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketene acetals</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Phenol ethers</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Vinyl chlorides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzyloxycarbonyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Chloroalkene</substituent>
      <substituent>Cyclopropanecarboxylic acid or derivatives</substituent>
      <substituent>Diaryl ether</substituent>
      <substituent>Diphenylether</substituent>
      <substituent>Ether</substituent>
      <substituent>Haloalkene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketene acetal or derivatives</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Pyrethroid skeleton</substituent>
      <substituent>Vinyl chloride</substituent>
      <substituent>Vinyl halide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Pyrethroid insecticides</descriptor>
      <descriptor>Pyrethroid pesticides</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.91e-05 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>391.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>390.0789499</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(C=C(Cl)Cl)[C@@]([H])(C(=O)OCC2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H20Cl2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3/t17-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RLLPVAHGXHCWKJ-HKUYNNGSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>35.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>114.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</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:0x00007f726ef83ad0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id/>
  <hmdb_id/>
  <pubchem_compound_id>40463</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>36968</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>
