<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2018-10-03 16:33:40 UTC</creation_date>
  <update_date>2020-06-04 18:57:22 UTC</update_date>
  <accession>BMDB0063615</accession>
  <secondary_accessions>
    <accession>BMDB63615</accession>
  </secondary_accessions>
  <name>p,p′-DDE</name>
  <description>1,1-Dichloro-2,2-bis(p-chlorophenyl) ethylene (DDE) is a breakdown product of DDT, which was used in the past as an insecticide. No information is available on the acute (short-term) or chronic (long-term) effects of DDE. Acute, oral exposure to high doses of DDT in humans results in central nervous system (CNS) effects, such as headaches, nausea, and convulsions. The only effect noted in epidemiologic studies of workers exposed to DDT and other pesticides was an increase in activity of liver enzymes. Animal studies have reported effects on the liver, immune system, and CNS from chronic oral exposure to DDT. Human studies are inconclusive regarding DDE and cancer. Animal studies have reported an increased incidence of liver tumors in mice and hamsters, and thyroid tumors in female rats from oral exposure to DDE. EPA has classified DDE as a Group B2, probable human carcinogen.</description>
  <synonyms>
    <synonym>1,1-Dichloro-2,2-bis(4'-chlorophenyl)ethylene</synonym>
    <synonym>1,1-Dichloro-2,2-bis(4-chlorophenyl)ethylene</synonym>
    <synonym>4,4'-DDE</synonym>
    <synonym>p,P'-(dichlorodiphenyl)-2,2-dichloroethylene</synonym>
    <synonym>p,P'-dde</synonym>
    <synonym>DDE</synonym>
    <synonym>1,1-Dichloro-2,2-bis(p-chlorophenyl)ethylene</synonym>
    <synonym>DDMU</synonym>
    <synonym>DDX</synonym>
    <synonym>Dichlorodiphenyl dichloroethylene</synonym>
    <synonym>Dichloroethylene, dichlorodiphenyl</synonym>
    <synonym>p,p-Dichlorodiphenyldichloroethylene</synonym>
  </synonyms>
  <chemical_formula>C14H8Cl4</chemical_formula>
  <average_molecular_weight>318.025</average_molecular_weight>
  <monisotopic_moleculate_weight>315.938011084</monisotopic_moleculate_weight>
  <iupac_name>1-chloro-4-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene</iupac_name>
  <traditional_iupac>p,p'-DDE</traditional_iupac>
  <cas_registry_number>72-55-9</cas_registry_number>
  <smiles>ClC(Cl)=C(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1</smiles>
  <inchi>InChI=1S/C14H8Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8H</inchi>
  <inchikey>UCNVFOCBFJOQAL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Diphenylmethanes</sub_class>
    <direct_parent>Diphenylmethanes</direct_parent>
    <alternative_parents>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Chloroalkenes</alternative_parent>
      <alternative_parent>Chlorobenzenes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketene acetals</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Vinyl chlorides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Chloroalkene</substituent>
      <substituent>Chlorobenzene</substituent>
      <substituent>Diphenylmethane</substituent>
      <substituent>Haloalkene</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketene acetal or derivatives</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Vinyl chloride</substituent>
      <substituent>Vinyl halide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Organochlorine pesticides</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>chlorophenylethylene</external_descriptor>
      <external_descriptor>monochlorobenzenes</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state/>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-chloro-4-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>318.025</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>315.938011084</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>ClC(Cl)=C(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H8Cl4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H8Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8H</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UCNVFOCBFJOQAL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>99.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</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>2</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::EiMs</type>
      <spectrum_id>1027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3299</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0641 +/- 0.0830</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>
  <foodb_id>FDB097419</foodb_id>
  <chemspider_id>2927</chemspider_id>
  <pubchem_compound_id>3035</pubchem_compound_id>
  <knapsack_id/>
  <pdbe_id/>
  <chebi_id>16598</chebi_id>
  <kegg_id>C04596</kegg_id>
  <meta_cyc_id/>
  <wikipedia_id>Dichlorodiphenyldichloroethylene</wikipedia_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_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>
