<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:41 UTC</creation_date>
  <update_date>2025-11-18 23:28:46 UTC</update_date>
  <accession>FDB011524</accession>
  <name>Epiestradiol</name>
  <description>17a-estradiol is found in the estrogen patch. The estrogen patch is a delivery system for estradiol used as hormone replacement therapy to treat the symptoms of menopause, such as hot flashes and vaginal dryness, and to prevent osteoporosis. Originally marketed as Vivelle (Novartis), it was discontinued in 2003 and reintroduced in a smaller form as Vivelle-Dot. Although the estrogen is given transdermally rather than in the standard oral tablets, the estrogen patch carries similar risks and benefits as more conventional forms of estrogen-only hormone replacement therapy.</description>
  <synonyms>
    <synonym>(17alpha)-estra-1,3,5(10)-triene-3,17-diol</synonym>
    <synonym>&amp;alpha;-estradiol</synonym>
    <synonym>1,3,5-Estratriene-3,17&amp;alpha;-diol</synonym>
    <synonym>1,3,5-Estratriene-3,17a-diol</synonym>
    <synonym>1,3,5(10)-Estratriene-3,17alpha-diol</synonym>
    <synonym>13b-Methyl-1,3,5(10)-gonatriene-3,17a-diol</synonym>
    <synonym>17-alpha-Estradiol</synonym>
    <synonym>17-Epiestradiol</synonym>
    <synonym>17&amp;alpha;-Estradiol</synonym>
    <synonym>17&amp;alpha;-Oestradiol</synonym>
    <synonym>17a-Estradiol</synonym>
    <synonym>17a-Oestradiol</synonym>
    <synonym>17alpha estradiol</synonym>
    <synonym>17alpha-Estradiol</synonym>
    <synonym>17α-estradiol</synonym>
    <synonym>3, 17-Dihydroxyestratriene</synonym>
    <synonym>3, 17&amp;alpha;-Dihydroxyestra-1,3,5(10)-triene</synonym>
    <synonym>3, 17&amp;alpha;-Dihydroxyoestra-1,3,5(10)-triene</synonym>
    <synonym>3,17-Dihydroxyestratriene</synonym>
    <synonym>3,17&amp;alpha;-Dihydroxyestra-1,3,5(10)-triene</synonym>
    <synonym>3,17&amp;alpha;-Dihydroxyoestra-1,3,5(10)-triene</synonym>
    <synonym>3,17a-Dihydroxyestra-1,3,5(10)-triene</synonym>
    <synonym>3,17a-Dihydroxyoestra-1,3,5(10)-triene</synonym>
    <synonym>3,17alpha-Dihydroxy-1,3,5(10)-estratriene</synonym>
    <synonym>5A-Estran-3A,17B-diol</synonym>
    <synonym>A-estradiol</synonym>
    <synonym>Alfatradiol</synonym>
    <synonym>Alfatradiol (inn)</synonym>
    <synonym>Alfatradiol, INN</synonym>
    <synonym>Alpha-estradiol</synonym>
    <synonym>b-Estradiol (obsol., misleading)</synonym>
    <synonym>Epiestradiol</synonym>
    <synonym>Epiestrol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3, 17&amp;alpha;-diol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,17-diol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,17-diol, (17&amp;alpha;)-</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,17&amp;alpha;-diol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,17a-diol</synonym>
    <synonym>estra-1,3,5(10)-triene-3,17alpha-diol</synonym>
    <synonym>Estra-1,3,5(10)trien-3,17a-diol</synonym>
    <synonym>Estra-1,3,5(10)trien-3,17alpha-diol</synonym>
    <synonym>Estra-1,3,5(10)trien-3,17α-diol</synonym>
    <synonym>Estradiol</synonym>
    <synonym>Estradiol-17a</synonym>
    <synonym>estradiol-17alpha</synonym>
    <synonym>Estradiol-17α</synonym>
    <synonym>Estradiol, 17&amp;alpha;-</synonym>
    <synonym>Oestra-1,3,5(10)-triene-3, 17&amp;alpha;-diol</synonym>
    <synonym>Oestra-1,3,5(10)-triene-3,17&amp;alpha;-diol</synonym>
    <synonym>Oestra-1,3,5(10)-triene-3,17a-diol</synonym>
    <synonym>Oestradiol-17&amp;alpha;</synonym>
    <synonym>α-estradiol</synonym>
  </synonyms>
  <chemical_formula>C18H24O2</chemical_formula>
  <average_molecular_weight>272.382</average_molecular_weight>
  <monisotopic_moleculate_weight>272.177630012</monisotopic_moleculate_weight>
  <iupac_name>15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,14-diol</iupac_name>
  <traditional_iupac>15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,14-diol</traditional_iupac>
  <cas_registry_number>57-91-0</cas_registry_number>
  <smiles>CC12CCC3C(CCC4=C3C=CC(O)=C4)C1CCC2O</smiles>
  <inchi>InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3</inchi>
  <inchikey>VOXZDWNPVJITMN-UHFFFAOYSA-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>
    <direct_parent>Estrogens 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>Estrane steroids</sub_class>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a steroid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.13e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 223°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.75</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>10.33</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-0.88</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,14-diol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>272.382</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>272.177630012</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC12CCC3C(CCC4=C3C=CC(O)=C4)C1CCC2O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C18H24O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>VOXZDWNPVJITMN-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>40.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>79.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>31.86</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>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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3394312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3394313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3394314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3394315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3394316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3394317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>113972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>127897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>808195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>808196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>808197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>808198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>808199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>808200</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB00429</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>17160</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31680380&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31680128&gt;</reference>
    <reference>#&lt;Reference:0x000055ce3167be98&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Apricot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Prunus armeniaca</name_scientific>
      <ncbi_taxonomy_id>36596</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Milk (Cow)</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>0.000124</average_value>
      <max_value>0.000145</max_value>
      <min_value>0.000111</min_value>
      <unit>uM</unit>
    </food>
    <food>
      <name>Pomegranate</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Punica granatum</name_scientific>
      <ncbi_taxonomy_id>22663</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
