<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:27:17 UTC</creation_date>
  <update_date>2015-07-21 06:57:37 UTC</update_date>
  <accession>FDB023274</accession>
  <name>19-Oxotestosterone</name>
  <description>19-Oxotestosterone is catalyzed by Aromatase (EC 1.14.14.1),also called estrogen synthetase (a cytochrome P450 enzyme which catalyzes the formation of aromatic C18 estrogens from C19 androgens; it is symbolized CYP19) into oestrogens via sequential oxidations at the 19-methyl group. Biosynthesis of estrogens from C19 steroids is catalyzed by aromatase and its tissue-specific expression is determined at least in part by alternative use of tissue-specific promoters, which give rise to transcripts with unique 5-prime noncoding termini.(OMIM 107910) [HMDB]</description>
  <synonyms>
  </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,10R,11R,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10R,11R,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number>4075-13-2</cas_registry_number>
  <smiles>[H][C@@]1(O)CC[C@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])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/h11,14-17,21H,3-10H2,1-2H3/t14-,15+,16-,17+,18-,19-/m0/s1</inchi>
  <inchikey>MUMGGOZAMZWBJJ-WXJALIKYSA-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-4-steroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</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>Cyclohexenone</substituent>
      <substituent>Delta-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>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.33e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.37</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>19.09</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-0.88</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(1S,2R,10R,11R,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-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@@]1(O)CC[C@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])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/h11,14-17,21H,3-10H2,1-2H3/t14-,15+,16-,17+,18-,19-/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>MUMGGOZAMZWBJJ-WXJALIKYSA-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>84.43</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>33.84</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>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP00068</smpdb_id>
      <kegg_map_id>map00150</kegg_map_id>
    </pathway>
  </pathways>
  <spectra>
  </spectra>
  <hmdb_id>HMDB03959</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:0x000055ce32548700&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32548548&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32548390&gt;</reference>
    <reference>#&lt;Reference:0x000055ce325481d8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32548020&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32547e68&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32547cb0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32547af8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32547940&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32547788&gt;</reference>
    <reference>#&lt;Reference:0x000055ce325475d0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32547418&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32547260&gt;</reference>
    <reference>#&lt;Reference:0x000055ce325470a8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32546ef0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32546d38&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32546b80&gt;</reference>
    <reference>#&lt;Reference:0x000055ce325469c8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32546810&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32546658&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>3-oxo-5-beta-steroid 4-dehydrogenase</name>
      <uniprot_id>P51857</uniprot_id>
      <uniprot_name/>
      <gene_name>AKR1D1</gene_name>
    </enzyme>
    <enzyme>
      <name>Cytochrome P450 2D6</name>
      <uniprot_id>Q6NWU0</uniprot_id>
      <uniprot_name/>
      <gene_name>CYP2D6</gene_name>
    </enzyme>
    <enzyme>
      <name>Cytochrome P450, family 1, subfamily A, polypeptide 1</name>
      <uniprot_id>A0N0X8</uniprot_id>
      <uniprot_name/>
      <gene_name>CYP1A1</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
