<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:29:13 UTC</creation_date>
  <update_date>2015-07-21 06:57:41 UTC</update_date>
  <accession>FDB023389</accession>
  <name>4-Chloromethandienone</name>
  <description>4-Chloromethandienone is a synthetic anabolic steroid, suspected of misuse in sports. Although the widespread use of androgenic anabolic steroids might be implicated in the development of hormone-sensitive tumors, there are few reports regarding a possible causal relation between doping and cancer; however, there is one reported case of a 32-year-old man that underwent right radical orchiectomy for a tumor (identified as an intratesticular leiomyosarcoma) of the upper pole of the right testicle where the patient reported a 5-year history of systematic use of high dose of 4-Chloromethandienone. (PMID: 10526287) [HMDB]</description>
  <synonyms>
    <synonym>(17b)-4-chloro-17-hydroxy-17-methyl-Androsta-1,4-dien-3-one</synonym>
    <synonym>1-Dehydro-4-chloro-17-methyltestosterone</synonym>
    <synonym>1-Dehydro-4-chloro-17a-methyltestosterone</synonym>
    <synonym>4-Chloro-1-dehydro-17-methyltestosterone</synonym>
    <synonym>4-Chloro-1-dehydromethyltestosterone</synonym>
    <synonym>4-Chloro-1,2-dehydro-17a-methyltestosterone</synonym>
    <synonym>4-Chloro-17a-methyl-17b-hydroxyandrosta-1,4-dien-3-one</synonym>
    <synonym>4-chloro-17b-hydroxy-17-methyl-Androsta-1,4-dien-3-one</synonym>
    <synonym>4-Chloro-17b-hydroxy-17a-methyl-5a-androsta-1,4-dien-3-one</synonym>
    <synonym>4-chlorodehydromethyltestosterone</synonym>
    <synonym>4-Chlorodianabol</synonym>
    <synonym>CDMT</synonym>
    <synonym>Oral-Turinabol</synonym>
    <synonym>Turinabol-oral</synonym>
  </synonyms>
  <chemical_formula>C20H27ClO2</chemical_formula>
  <average_molecular_weight>334.88</average_molecular_weight>
  <monisotopic_moleculate_weight>334.169957815</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10R,11S,14S,15S)-6-chloro-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one</iupac_name>
  <traditional_iupac>oral turinabol</traditional_iupac>
  <cas_registry_number>2446-23-3</cas_registry_number>
  <smiles>[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(Cl)C(=O)C=C[C@]12C</smiles>
  <inchi>InChI=1S/C20H27ClO2/c1-18-9-8-16(22)17(21)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h8-9,12-14,23H,4-7,10-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1</inchi>
  <inchikey>AGUNEISBPXQOPA-XMUHMHRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <direct_parent>Androgens and derivatives</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-oxo delta-1,4-steroids</alternative_parent>
      <alternative_parent>Alpha-chloroketones</alternative_parent>
      <alternative_parent>Chloroalkenes</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Delta-1,4-steroids</alternative_parent>
      <alternative_parent>Halogenated steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Vinyl chlorides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-1,4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>4-halo-steroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-chloroketone</substituent>
      <substituent>Alpha-haloketone</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Chloroalkene</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Delta-1,4-steroid</substituent>
      <substituent>Halo-steroid</substituent>
      <substituent>Haloalkene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Vinyl chloride</substituent>
      <substituent>Vinyl halide</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.75e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.03</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-0.53</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(1S,2R,10R,11S,14S,15S)-6-chloro-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>334.88</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>334.169957815</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(Cl)C(=O)C=C[C@]12C</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C20H27ClO2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C20H27ClO2/c1-18-9-8-16(22)17(21)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h8-9,12-14,23H,4-7,10-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>AGUNEISBPXQOPA-XMUHMHRVSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>37.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>94.95</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>37.26</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>1</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>153796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2287818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2287819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2287820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2648487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2648488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2648489</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB04634</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce323c0b80&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
