<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:09:47 UTC</creation_date>
  <update_date>2020-04-22 15:13:54 UTC</update_date>
  <accession>BMDB0004611</accession>
  <secondary_accessions>
    <accession>BMDB04611</accession>
  </secondary_accessions>
  <name>7a-Hydroxydehydroepiandrosterone</name>
  <description/>
  <synonyms>
    <synonym>(3beta,7alpha)-3,7-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>3beta,7alpha-Dihydroxy-5-androstene-17-one</synonym>
    <synonym>3beta,7alpha-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>7alpha-Hydroxy-dhea</synonym>
    <synonym>7alpha-OH-DHEA</synonym>
    <synonym>(3b,7a)-3,7-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>(3Β,7α)-3,7-dihydroxyandrost-5-en-17-one</synonym>
    <synonym>3b,7a-Dihydroxy-5-androstene-17-one</synonym>
    <synonym>3Β,7α-dihydroxy-5-androstene-17-one</synonym>
    <synonym>3b,7a-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>3Β,7α-dihydroxyandrost-5-en-17-one</synonym>
    <synonym>7a-Hydroxy-dhea</synonym>
    <synonym>7Α-hydroxy-dhea</synonym>
    <synonym>7a-OH-DHEA</synonym>
    <synonym>7Α-OH-dhea</synonym>
    <synonym>7-Hydroxydehydroepiandrosterone</synonym>
    <synonym>7beta-Hydroxydehydroepiandrosterone</synonym>
    <synonym>7-Hydroxydehydroepiandrosterone, (3beta)-isomer</synonym>
    <synonym>7beta-OH-DHEA</synonym>
    <synonym>7 alpha-Hydroxydehydroepiandrosterone</synonym>
    <synonym>7-Hydroxydehydroepiandrosterone, (3beta,7beta)-isomer</synonym>
    <synonym>(-)-7a-Hydroxydehydroepiandrosterone</synonym>
    <synonym>(3b,7a)-3,7-Dihydroxy-androst-5-en-17-one</synonym>
    <synonym>3b,7a-Dihydroxy-5-androsten-17-one</synonym>
    <synonym>3b,7a-Dihydroxy-androst-5-en-17-one</synonym>
    <synonym>7-a-OH-DHEA</synonym>
    <synonym>7-alpha-OH-DHEA</synonym>
    <synonym>7a-Hydroxydehydroisoandrosterone</synonym>
  </synonyms>
  <chemical_formula>C19H28O3</chemical_formula>
  <average_molecular_weight>304.4238</average_molecular_weight>
  <monisotopic_moleculate_weight>304.203844762</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,9S,10R,11S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one</iupac_name>
  <traditional_iupac>7β-oh-dhea</traditional_iupac>
  <cas_registry_number>53-00-9</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15+,17-,18-,19-/m0/s1</inchi>
  <inchikey>OLPSAOWBSPXZEA-JIEICEMKSA-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-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</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-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-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>3-hydroxy steroid</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>182 - 183 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.21</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>-0.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,9S,10R,11S,15S)-5,9-dihydroxy-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>304.4238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>304.203844762</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15+,17-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OLPSAOWBSPXZEA-JIEICEMKSA-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>86.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.78</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>22478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>145809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3048023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3048024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3048025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3095848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3095849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3095850</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C18045</kegg_id>
  <chemspider_id>58963</chemspider_id>
  <pubchem_compound_id>65517</pubchem_compound_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <foodb_id>FDB023382</foodb_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>7alpha-Hydroxy-DHEA</wikipedia_id>
  <metlin_id/>
  <pdbe_id></pdbe_id>
  <chebi_id>712194</chebi_id>
  <synthesis_reference>Ishidate, Morizo; Okada, Masashi.  Steroids.    (1963),     2 pp.  JP  38023170  19631031  Showa.   CAN 60:12972  AN 1964:12972</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
