<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-06-03 10:55:47 UTC</creation_date>
  <update_date>2026-03-27 01:56:56 UTC</update_date>
  <accession/>
  <common_name>(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)methyl (1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate</common_name>
  <class>SmallMolecule</class>
  <description>(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)methyl (1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate belongs to the isoindolines, a subclass of isoindoles and derivatives within the organic compounds. This organoheterocyclic compound has the chemical formula C19H25NO4 and an average molecular weight of 331.41 g/mol.

The substance is found in or released from five recorded sources. These include household cleaning and consumer products such as tobacco smoke filters and cigar cigarettes, as well as building and construction materials like tents or canopies. Additionally, it is associated with electrical and electronic equipment, specifically discharge lamps, and is present in the preparation of malt within food, food processing, and cookware.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C19H25NO4</chemical_formula>
  <average_molecular_weight>331.412</average_molecular_weight>
  <monisotopic_moleculate_weight>331.178358289</monisotopic_moleculate_weight>
  <iupac_name>(1,3-dioxo-2,3,4,5,6,7-hexahydro-1H-isoindol-2-yl)methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate</iupac_name>
  <traditional_iupac>tetramethrin</traditional_iupac>
  <cas_registry_number>769-12-0</cas_registry_number>
  <smiles>[H][C@@]1(C=C(C)C)[C@@]([H])(C(=O)OCN2C(=O)C3=C(CCCC3)C2=O)C1(C)C</smiles>
  <inchi>InChI=1S/C19H25NO4/c1-11(2)9-14-15(19(14,3)4)18(23)24-10-20-16(21)12-7-5-6-8-13(12)17(20)22/h9,14-15H,5-8,10H2,1-4H3/t14-,15+/m1/s1</inchi>
  <inchikey>CXBMCYHAMVGWJQ-CABCVRRESA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Isoindoles and derivatives</class>
    <sub_class>Isoindolines</sub_class>
    <direct_parent>Isoindolones</direct_parent>
    <alternate_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Bicyclic monoterpenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Cyclopropanecarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Dicarboximides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Isoindoles</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Maleimides</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-substituted carboxylic acid imides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Bicyclic monoterpenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid imide</substituent>
      <substituent>Carboxylic acid imide, n-substituted</substituent>
      <substituent>Cyclopropanecarboxylic acid or derivatives</substituent>
      <substituent>Dicarboximide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoindole</substituent>
      <substituent>Isoindolone</substituent>
      <substituent>Lactam</substituent>
      <substituent>Maleimide</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monoterpenoid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrroline</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <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>2.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.54e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1,3-dioxo-2,3,4,5,6,7-hexahydro-1H-isoindol-2-yl)methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>331.412</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>331.178358289</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(C=C(C)C)[C@@]([H])(C(=O)OCN2C(=O)C3=C(CCCC3)C2=O)C1(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H25NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H25NO4/c1-11(2)9-14-15(19(14,3)4)18(23)24-10-20-16(21)12-7-5-6-8-13(12)17(20)22/h9,14-15H,5-8,10H2,1-4H3/t14-,15+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CXBMCYHAMVGWJQ-CABCVRRESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>90.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</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:0x00007f726c8c2450&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id/>
  <hmdb_id/>
  <pubchem_compound_id>24365</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>22780</chemspider_id>
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  <wikipidia/>
  <general_references/>
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</compound>
