<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2018-10-03 16:32:54 UTC</creation_date>
  <update_date>2020-06-04 18:57:41 UTC</update_date>
  <accession>BMDB0063606</accession>
  <secondary_accessions>
    <accession>BMDB63606</accession>
  </secondary_accessions>
  <name>delta-Hexachlorocyclohexane</name>
  <description>Delta-hexachlorocyclohexane (delta-HCH) is a solid. It is a component of technical grade HCH. The interaction of delta-HCH with human red blood cells disrupts membrane structure and changes the environment of cytoskeleton proteins that could cause cell lysis.  No neoplastic or nonneoplastic effects were noted in livers of male mice or rats given dietary delta-HCH at concentrations ranging from 100-1000 ppm. delta-HCH was particularly potent toward disrupting Ca2+ homeostasis in a variety of excitable and nonexcitable cells and altering contractility of cardiac muscle. delta-HCH interacts with cardiac ryanodine-sensitive Ca2+ channels (RyR2), accounting in part for altered Ca2+ transients and contractility. delta-HCH increases the ionic permeability of phospholipid membranes by two distinct Ca2+-dependent mechanisms: one mediated through RyR and the other mediated by a unique ionophore activity.</description>
  <synonyms>
    <synonym>(1alpha,2alpha,3alpha,4beta,5alpha,6beta)-1,2,3,4,5,6-Hexachlorocyclohexane</synonym>
    <synonym>(1R,2C,3C,4t,5C,6t)-1,2,3,4,5,6-Hexachlorocyclohexane</synonym>
    <synonym>delta-Benzene hexachloride</synonym>
    <synonym>delta-BHC</synonym>
    <synonym>delta-Lindane</synonym>
    <synonym>(1a,2a,3a,4b,5a,6b)-1,2,3,4,5,6-Hexachlorocyclohexane</synonym>
    <synonym>(1Α,2α,3α,4β,5α,6β)-1,2,3,4,5,6-hexachlorocyclohexane</synonym>
    <synonym>Δ-benzene hexachloride</synonym>
    <synonym>Δ-BHC</synonym>
    <synonym>Δ-lindane</synonym>
    <synonym>Δ-hexachlorocyclohexane</synonym>
  </synonyms>
  <chemical_formula>C6H6Cl6</chemical_formula>
  <average_molecular_weight>290.83</average_molecular_weight>
  <monisotopic_moleculate_weight>287.860066434</monisotopic_moleculate_weight>
  <iupac_name>(1R,2S,3r,4R,5S,6s)-1,2,3,4,5,6-hexachlorocyclohexane</iupac_name>
  <traditional_iupac>delta-BHC</traditional_iupac>
  <cas_registry_number>319-86-8</cas_registry_number>
  <smiles>[H][C@]1(Cl)[C@]([H])(Cl)[C@@]([H])(Cl)[C@]([H])(Cl)[C@]([H])(Cl)[C@]1([H])Cl</smiles>
  <inchi>InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4+,5-,6-</inchi>
  <inchikey>JLYXXMFPNIAWKQ-GPIVLXJGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cyclohexyl halides. These are organohalogen compounds containing a monocyclic cyclohexane moiety that is substituted at one or more positions by an halogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organohalogen compounds</super_class>
    <class>Alkyl halides</class>
    <sub_class>Cyclohexyl halides</sub_class>
    <direct_parent>Cyclohexyl halides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl chlorides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alkyl chloride</substituent>
      <substituent>Cyclohexyl halide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organochloride</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>hexachlorocyclohexane</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state/>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,2S,3r,4R,5S,6s)-1,2,3,4,5,6-hexachlorocyclohexane</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>290.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>287.860066434</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(Cl)[C@]([H])(Cl)[C@@]([H])(Cl)[C@]([H])(Cl)[C@]([H])(Cl)[C@]1([H])Cl</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H6Cl6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4+,5-,6-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JLYXXMFPNIAWKQ-GPIVLXJGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</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>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157010</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00138 +/- 0.00413</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw bovine milk from Haryana (n=147)</comment>
      <references>
        <reference>
          <reference_text>Sharma HR, Kaushik A, Kaushik CP: Pesticide residues in bovine milk from a predominantly agricultural state of Haryana, India. Environ Monit Assess. 2007 Jun;129(1-3):349-57. doi: 10.1007/s10661-006-9368-5. Epub 2006 Dec 16.</reference_text>
          <pubmed_id>17180431</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id/>
  <pubchem_compound_id/>
  <kegg_id/>
  <chebi_id>39095</chebi_id>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <foodb_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Sharma HR, Kaushik A, Kaushik CP: Pesticide residues in bovine milk from a predominantly agricultural state of Haryana, India. Environ Monit Assess. 2007 Jun;129(1-3):349-57. doi: 10.1007/s10661-006-9368-5. Epub 2006 Dec 16.</reference_text>
      <pubmed_id>17180431</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
