<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4845</id>
  <title>T3D4790</title>
  <common-name>Estriol</common-name>
  <description>A hydroxylated metabolite of estradiol or estrone that has a hydroxyl group at C3-beta, 16-alpha, and 17-beta position. Estriol is a major urinary estrogen. During pregnancy, large amount of estriol is produced by the placenta. Isomers with inversion of the hydroxyl group or groups are called epiestriol. Though estriol is used as part of the primarily North American phenomenon of bioidentical hormone replacement therapy, it is not approved for use by the FDA or Health Canada. It is however available in the United States by prescription filled only by compounding pharmacies. It has also been approved and marketed throughout Europe and Asia for approximately 40 years for the treatment of post-menopausal hot flashes.</description>
  <cas>50-27-1</cas>
  <pubchem-id>5756</pubchem-id>
  <chemical-formula>C18H24O3</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>82-86°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility nil="true"/>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity>Estriol levels can be measured to give an indication of the general health of the fetus. DHEA-S is produced by the adrenal cortex of the fetus. This is converted to estriol by the placenta. If levels of "unconjugated estriol" are abnormally low in a pregnant woman, this may indicate a problem with the development of the child. The drug interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estriol upon the target cell. Estrogens increase 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.</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity>ORAL (LD50): Acute: &gt;2000 mg/kg [Rat].</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Used as a test to determine the general health of an unborn fetus.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T05:16:42Z</created-at>
  <updated-at type="dateTime">2026-03-31T17:33:10Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Estriol</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C05141</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>27974</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB04573</drugbank-id>
  <pdb-id>ESL</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</moldb-smiles>
  <moldb-formula>C18H24O3</moldb-formula>
  <moldb-inchi>InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1</moldb-inchi>
  <moldb-inchikey>PROQIPRRNZUXQM-ZXXIGWHRSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">288.3814</moldb-average-mass>
  <moldb-mono-mass type="decimal">288.172544634</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp>2.45</logp>
  <hmdb-id>HMDB00153</hmdb-id>
  <chembl-id>CHEMBL193482</chembl-id>
  <chemspider-id>5553</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;James V. Freeman, Gary M. Johnson, &amp;#8220;Synthesis of 6.alpha.-functionalized estriol haptens and protein conjugates thereof.&amp;#8221; U.S. Patent US5902888, issued June, 1973.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003747</chemdb-id>
  <dsstox-id>DTXSID9022366</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00009155</susdat-id>
  <iupac>(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol</iupac>
</compound>
