<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:19:02 UTC</creation_date>
  <update_date>2020-04-22 15:16:29 UTC</update_date>
  <accession>BMDB0005832</accession>
  <secondary_accessions>
    <accession>BMDB05832</accession>
  </secondary_accessions>
  <name>6b-Hydroxymethandienone</name>
  <description/>
  <synonyms>
    <synonym>(6b,17b)-6,17-Dihydroxy-17-methyl-androsta-1,4-dien-3-one</synonym>
    <synonym>6b,17b-Dihydroxy-17-methyl-androsta-1,4-dien-3-one</synonym>
    <synonym>6b-Hydroxydianabol</synonym>
    <synonym>6b-Hydroxymethandrostenolone</synonym>
  </synonyms>
  <chemical_formula>C20H28O3</chemical_formula>
  <average_molecular_weight>316.4345</average_molecular_weight>
  <monisotopic_moleculate_weight>316.203844762</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,8R,10R,11S,14S,15S)-8,14-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one</iupac_name>
  <traditional_iupac>6b-hydroxydianabol</traditional_iupac>
  <cas_registry_number>33526-41-9</cas_registry_number>
  <smiles>[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)C2=CC(=O)C=C[C@]12C</smiles>
  <inchi>InChI=1S/C20H28O3/c1-18-7-4-12(21)10-16(18)17(22)11-13-14(18)5-8-19(2)15(13)6-9-20(19,3)23/h4,7,10,13-15,17,22-23H,5-6,8-9,11H2,1-3H3/t13-,14+,15+,17-,18-,19+,20+/m1/s1</inchi>
  <inchikey>OBCJFTMGLMNCTJ-INIPNLRTSA-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>
    <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>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-oxo delta-1,4-steroids</alternative_parent>
      <alternative_parent>6-hydroxysteroids</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>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-1,4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>6-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Delta-1,4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.53</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,8R,10R,11S,14S,15S)-8,14-dihydroxy-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>316.4345</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>316.203844762</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])C[C@@H](O)C2=CC(=O)C=C[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H28O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H28O3/c1-18-7-4-12(21)10-16(18)17(22)11-13-14(18)5-8-19(2)15(13)6-9-20(19,3)23/h4,7,10,13-15,17,22-23H,5-6,8-9,11H2,1-3H3/t13-,14+,15+,17-,18-,19+,20+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OBCJFTMGLMNCTJ-INIPNLRTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>91.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</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>4</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::CMs</type>
      <spectrum_id>15885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>166738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2665930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2665931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2665932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3012572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3012573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3012574</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB023778</foodb_id>
  <chemspider_id>10363911</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>13241205</pubchem_compound_id>
  <chebi_id/>
  <kegg_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Pryakhina, Z. A.; Grinenko, G. S.; Lisitsa, L. I.; Gritsina, G. I.  On the dehydrogenation of methytestosterone by selenious acid.    Khimiko-Farmatsevticheskii Zhurnal  (1976),  10(1),  115-17.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
