<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:22:38 UTC</creation_date>
  <update_date>2026-08-21 18:35:12 UTC</update_date>
  <accession/>
  <common_name>Naftifine</common_name>
  <class>SmallMolecule</class>
  <description>Naftifine is an organic compound with the formula C21H21N and an average molecular weight of 287.41 g/mol. Naftifine belongs to the naphthalenes, a class of benzenoids within the organic compounds. In terms of biological activity, it acts as an inhibitor of the protein target squalene monooxygenase (SQLE).

This compound is found in or released from four recorded sources: healthcare, pharmaceuticals and veterinary products, specifically antibiotics and antifungals for dermatological use; electrical and electronic equipment, specifically antennas; and household cleaning and consumer products, specifically other smoking requisites. Recorded exposure routes for Naftifine include topical, oral, and inhalation.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C21H21N</chemical_formula>
  <average_molecular_weight>287.406</average_molecular_weight>
  <monisotopic_moleculate_weight>287.16739968</monisotopic_moleculate_weight>
  <iupac_name>methyl[(naphthalen-1-yl)methyl][(2E)-3-phenylprop-2-en-1-yl]amine</iupac_name>
  <traditional_iupac>naftifine</traditional_iupac>
  <cas_registry_number>65472-88-0</cas_registry_number>
  <smiles>[H]\C(CN(C)CC1=CC=CC2=CC=CC=C12)=C(\[H])C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C21H21N/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20/h2-15H,16-17H2,1H3/b11-8+</inchi>
  <inchikey>OZGNYLLQHRPOBR-DHZHZOJOSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Naphthalenes</class>
    <sub_class/>
    <direct_parent>Naphthalenes</direct_parent>
    <alternate_parents>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Naphthalene</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Styrene</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>allylamine antifungal drug</descriptor>
      <descriptor>naphthalenes</descriptor>
      <descriptor>tertiary amine</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Naftifine Action Pathway</name>
      <smpdb_id>SMP0125827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Naftifine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143178</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>5.24</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.29e-04 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>methyl[(naphthalen-1-yl)methyl][(2E)-3-phenylprop-2-en-1-yl]amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>287.406</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>287.16739968</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]\C(CN(C)CC1=CC=CC2=CC=CC=C12)=C(\[H])C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H21N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H21N/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20/h2-15H,16-17H2,1H3/b11-8+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OZGNYLLQHRPOBR-DHZHZOJOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>3.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</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>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:0x00007f726c485798&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00735</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>73342</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>43344</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_id>BE0000577</target_id>
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  </targets>
</compound>
