<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:19:24 UTC</creation_date>
  <update_date>2020-04-22 15:16:36 UTC</update_date>
  <accession>BMDB0005962</accession>
  <secondary_accessions>
    <accession>BMDB05962</accession>
  </secondary_accessions>
  <name>Dehydroandrosterone</name>
  <description/>
  <synonyms>
    <synonym>3a-Hydroxy-5-androsten-17-one</synonym>
    <synonym>3a-Hydroxy-androst-5-en-17-one</synonym>
    <synonym>Androst-5-en-3a-ol-17-one</synonym>
    <synonym>D5-Androstene-3a-ol-17-one</synonym>
    <synonym>Isoandrostenolone</synonym>
    <synonym>Androstenolone</synonym>
    <synonym>Dehydroisoandrosterone</synonym>
    <synonym>5 Androsten 3 beta hydroxy 17 one</synonym>
    <synonym>5 Androsten 3 ol 17 one</synonym>
    <synonym>5-Androsten-3-ol-17-one</synonym>
    <synonym>DHEA</synonym>
    <synonym>Dehydroepiandrosterone</synonym>
    <synonym>5-Androsten-3-beta-hydroxy-17-one</synonym>
    <synonym>Prasterone</synonym>
    <synonym>Prasterone, 3 alpha isomer</synonym>
    <synonym>Prasterone, 3 alpha-isomer</synonym>
  </synonyms>
  <chemical_formula>C19H28O2</chemical_formula>
  <average_molecular_weight>288.4244</average_molecular_weight>
  <monisotopic_moleculate_weight>288.20893014</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one</iupac_name>
  <traditional_iupac>dehydroandrosterone</traditional_iupac>
  <cas_registry_number>2283-82-1</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14+,15+,16+,18+,19+/m1/s1</inchi>
  <inchikey>FMGSKLZLMKYGDP-HKQXQEGQSA-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-oxosteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-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>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>148 - 150 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>288.4244</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>288.20893014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14+,15+,16+,18+,19+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FMGSKLZLMKYGDP-HKQXQEGQSA-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>84.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.96</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>
    <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::MsMs</type>
      <spectrum_id>305140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2706851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2706852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2706853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2998073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2998074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2998075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>137777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>145511</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB023792</foodb_id>
  <chemspider_id>118560</chemspider_id>
  <pubchem_compound_id>134506</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <knapsack_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Dehydroepiandrosterone</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Butenandt, Adolf; Dannenbaum, Hans; Hanisch, Gunter; Kudszus, Helmut.  Dehydroandrosterone.    Z. physiol. Chem.  (1935),  237  57-74.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
