<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:01:17 UTC</creation_date>
  <update_date>2020-04-22 15:11:17 UTC</update_date>
  <accession>BMDB0002697</accession>
  <secondary_accessions>
    <accession>BMDB02697</accession>
  </secondary_accessions>
  <name>19-Norandrosterone</name>
  <description/>
  <synonyms>
    <synonym>19-Noreoiandrosterone</synonym>
    <synonym>19-Noretiocholanolone</synonym>
    <synonym>3-Hydroxyestran-17-one</synonym>
    <synonym>19-Norandrosterone, (3alpha,5alpha)-isomer</synonym>
    <synonym>(3alpha,5alpha)-3-Hydroxyestran-17-one</synonym>
    <synonym>(3Α,5α)-3-hydroxyestran-17-one</synonym>
    <synonym>3alpha-Hydroxy-5alpha-estran-17-one</synonym>
    <synonym>3Α-hydroxy-5α-estran-17-one</synonym>
    <synonym>5alpha-Estran-3alpha-ol-17-one</synonym>
    <synonym>5Α-estran-3α-ol-17-one</synonym>
    <synonym>19-Norandrosterone</synonym>
  </synonyms>
  <chemical_formula>C18H28O2</chemical_formula>
  <average_molecular_weight>276.42</average_molecular_weight>
  <monisotopic_moleculate_weight>276.208930142</monisotopic_moleculate_weight>
  <iupac_name>(1R,2S,5R,7S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</iupac_name>
  <traditional_iupac>(1R,2S,5R,7S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</traditional_iupac>
  <cas_registry_number>65556-19-6</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12[H]</smiles>
  <inchi>InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h11-16,19H,2-10H2,1H3/t11-,12+,13-,14+,15+,16-,18-/m0/s1</inchi>
  <inchikey>UOUIARGWRPHDBX-CQZDKXCPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</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-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</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>17-oxo steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>162 - 163 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.887</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,2S,5R,7S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>276.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>276.208930142</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[C@@]2([H])C[C@H](O)CC[C@]12[H]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H28O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h11-16,19H,2-10H2,1H3/t11-,12+,13-,14+,15+,16-,18-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UOUIARGWRPHDBX-CQZDKXCPSA-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>79.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.94</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::CMs</type>
      <spectrum_id>133438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>141172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2391325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2391326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2391327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2570462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2570463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2570464</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB023046</foodb_id>
  <chemspider_id>7827676</chemspider_id>
  <pubchem_compound_id>9548753</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>36412</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <wikipedia_id>19-Norandrosterone</wikipedia_id>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference>Caglioti, L.; Cainelli, G.; Maina, G.; Selva, A.  Hydroboration. V. New synthesis of androsterone and 19-norandrosterone.    Tetrahedron  (1964),  20(4),  957-61.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
