<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-19 02:39:14 UTC</creation_date>
  <update_date>2026-05-14 18:45:08 UTC</update_date>
  <accession/>
  <common_name>2-Hydroxyestradiol</common_name>
  <class>SmallMolecule</class>
  <description>2-Hydroxyestradiol is an organic compound with the formula C18H24O3 and an average molecular weight of 288.38 g/mol. 2-Hydroxyestradiol belongs to the estrane steroids, a subclass of steroids and steroid derivatives within the organic compounds. This substance is recorded as being found in or released from electrical and electronic equipment, specifically antennas and radio transmission systems.

Regarding its biological activity, histidine kinase (cyaC) is a recorded protein target for 2-Hydroxyestradiol. The compound is associated with several health effects, including obesity (PMC8632231) and cryptorchidism (PMC4977511).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C18H24O3</chemical_formula>
  <average_molecular_weight>288.3814</average_molecular_weight>
  <monisotopic_moleculate_weight>288.172544634</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol</iupac_name>
  <traditional_iupac>(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol</traditional_iupac>
  <cas_registry_number>362-05-0</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3</smiles>
  <inchi>InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1</inchi>
  <inchikey>DILDHNKDVHLEQB-XSSYPUMDSA-N</inchikey>
  <taxonomy>
    <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>
    <alternate_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>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>2-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>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>17beta-hydroxy steroid</descriptor>
      <descriptor>2-hydroxy steroid</descriptor>
      <descriptor>C18 steroids (estrogens) and derivatives</descriptor>
      <descriptor>C18 steroids (estrogens) and derivatives</descriptor>
      <descriptor>Estrane and derivatives</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Levonorgestrel Action Pathway</name>
      <smpdb_id>SMP0125332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Norgestrel Action Pathway</name>
      <smpdb_id>SMP0126522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Etonogestrel Action Pathway</name>
      <smpdb_id>SMP0126525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Megestrol acetate Action Pathway</name>
      <smpdb_id>SMP0126528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Progesterone Action Pathway</name>
      <smpdb_id>SMP0126529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Norethisterone Action Pathway</name>
      <smpdb_id>SMP0126536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Drospirenone Action Pathway</name>
      <smpdb_id>SMP0126538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Norelgestromin Action Pathway</name>
      <smpdb_id>SMP0126539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dienogest Action Pathway</name>
      <smpdb_id>SMP0126541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Segesterone acetate Action Pathway</name>
      <smpdb_id>SMP0126542</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>3.44</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.11e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.67</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,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>288.3814</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>288.172544634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H24O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DILDHNKDVHLEQB-XSSYPUMDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>81.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.08</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>3</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f86b0e430c0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB07706</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>247304</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>9303</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
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      <target_id>BE0002733</target_id>
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  </targets>
</compound>
