<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4799</id>
  <title>T3D4744</title>
  <common-name>Diethylstilbestrol</common-name>
  <description>A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen.</description>
  <cas>56-53-1</cas>
  <pubchem-id>448537</pubchem-id>
  <chemical-formula>C18H20O2</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>172°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>12 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity>Estrogens diffuse into their target cells and interact with a protein receptor, the estrogen receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. The effect of Estrogen binding their receptors causes downstream increases the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).</mechanism-of-toxicity>
  <metabolism>Hepatic.</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>1, carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>Used in the treatment of prostate cancer. Previously used in the prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T05:14:27Z</created-at>
  <updated-at type="dateTime">2026-03-31T19:50:24Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Diethylstilbestrol</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07620</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>4531</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB00255</drugbank-id>
  <pdb-id>DES</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC\C(=C(\CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1</moldb-smiles>
  <moldb-formula>C18H20O2</moldb-formula>
  <moldb-inchi>InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+</moldb-inchi>
  <moldb-inchikey>RGLYKWWBQGJZGM-ISLYRVAYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">268.356</moldb-average-mass>
  <moldb-mono-mass type="decimal">268.146329884</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>5.07</logp>
  <hmdb-id>HMDB14400</hmdb-id>
  <chembl-id>CHEMBL411</chembl-id>
  <chemspider-id>2946</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Adler, E.,Gie, G.J. and von Euler, H.; US. Patent 2,421,401; June 3, 1947; assigned to Hoffmann-La Roche, Inc.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003701</chemdb-id>
  <dsstox-id>DTXSID3020465</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00010902</susdat-id>
  <iupac>4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol</iupac>
</compound>
