<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:01:26 UTC</creation_date>
  <update_date>2020-05-11 20:55:57 UTC</update_date>
  <accession>BMDB0002725</accession>
  <secondary_accessions>
    <accession>BMDB02725</accession>
  </secondary_accessions>
  <name>Nandrolone</name>
  <description/>
  <synonyms>
    <synonym>(17beta)-17-Hydroxyestr-4-en-3-one</synonym>
    <synonym>17beta-Hydroxy-19-nor-4-androsten-3-one</synonym>
    <synonym>17beta-Hydroxy-4-estren-3-one</synonym>
    <synonym>17beta-Hydroxyestr-4-en-3-one</synonym>
    <synonym>19-Norandrostenolone</synonym>
    <synonym>19-Nortestosterone</synonym>
    <synonym>4-Estren-17beta-ol-3-one</synonym>
    <synonym>Decadura</synonym>
    <synonym>(17b)-17-Hydroxyestr-4-en-3-one</synonym>
    <synonym>(17Β)-17-hydroxyestr-4-en-3-one</synonym>
    <synonym>17b-Hydroxy-19-nor-4-androsten-3-one</synonym>
    <synonym>17Β-hydroxy-19-nor-4-androsten-3-one</synonym>
    <synonym>17b-Hydroxy-4-estren-3-one</synonym>
    <synonym>17Β-hydroxy-4-estren-3-one</synonym>
    <synonym>17b-Hydroxyestr-4-en-3-one</synonym>
    <synonym>17Β-hydroxyestr-4-en-3-one</synonym>
    <synonym>4-Estren-17b-ol-3-one</synonym>
    <synonym>4-Estren-17β-ol-3-one</synonym>
    <synonym>(17-beta)-17-Hydroxyestr-4-en-3-one</synonym>
    <synonym>17-beta-Hydroestr-4-en-3-one</synonym>
    <synonym>Deca-durabolin</synonym>
    <synonym>Durabolin</synonym>
    <synonym>Menidrabol</synonym>
    <synonym>Nandrolon</synonym>
    <synonym>Nandrolona</synonym>
    <synonym>Nandrolone base</synonym>
    <synonym>Nandrolone decanoate</synonym>
    <synonym>Nandrolone decanoic acid</synonym>
    <synonym>Nandrolone phenpropionate</synonym>
    <synonym>Nandrolonum</synonym>
    <synonym>Norandrostenolon</synonym>
    <synonym>Norandrostenolone</synonym>
    <synonym>Nortestonate</synonym>
    <synonym>Nortestosterone</synonym>
    <synonym>Nortestosteronum</synonym>
    <synonym>Oestrenolon</synonym>
    <synonym>17-Hydroxy-estr-4-ene-3-one</synonym>
    <synonym>Estrenolone</synonym>
    <synonym>17beta Hydroxy 19 nor 4 androsten 3 one</synonym>
  </synonyms>
  <chemical_formula>C18H26O2</chemical_formula>
  <average_molecular_weight>274.3978</average_molecular_weight>
  <monisotopic_moleculate_weight>274.193280076</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number>434-22-0</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]</smiles>
  <inchi>InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1</inchi>
  <inchikey>NPAGDVCDWIYMMC-IZPLOLCNSA-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-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>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</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>17beta-hydroxy steroid</external_descriptor>
      <external_descriptor>3-oxo Delta(4)-steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>Estrane and derivatives</external_descriptor>
      <external_descriptor>anabolic androgenic steroid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>118 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>3.09 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.62</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.28</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,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[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>274.3978</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>274.193280076</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H26O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NPAGDVCDWIYMMC-IZPLOLCNSA-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>79.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.27</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>87897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>87898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>87899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>150507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>150508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>150509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2236466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2236896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2238575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2239021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2241010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2242783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2243073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2244878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2245254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2247787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2689610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2689611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2689612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>155241</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adrenal Gland</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Epidermis</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Hair</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Skeletal Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB023054</foodb_id>
  <drugbank_id>DB13169</drugbank_id>
  <chemspider_id>9520</chemspider_id>
  <pubchem_compound_id>9904</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <kegg_id>C07254</kegg_id>
  <knapsack_id/>
  <chebi_id>7466</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Nandrolone</wikipedia_id>
  <metlin_id>1434</metlin_id>
  <synthesis_reference>Nomine Gerard, Bertin Daniel, Tessier Jean, Pierdet Andre, Bucourt Robert.  Process for the preparation of 19-nortestosterone and compounds used in this process.  1963, US Patent 3101354A (https://patents.google.com/patent/US3101354)</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
