Estriol

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'''Estriol''' Pubchem(5756) (also '''oestriol''') is one of the three main [[estrogen]]s produced by the human body. It is only produced in significant amounts during [[pregnancy]] as it is made by the [[placenta]]. In pregnant women with [[multiple sclerosis]] (MS), estriol reduces the disease's symptoms noticeably, according to researchers at UCLA's Geffen Medical School. 
 
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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.
 
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'''Drug Type''':  Small Molecule; Approved
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<script>spin on;color atoms amino;</script>
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<uploadedFileContents>NPH162.SDF</uploadedFileContents>
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</td></tr></table>
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==Description==
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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.
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==General Properties==
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'''Pharmacology''': Estriol (also oestriol) is one of the three main estrogens produced by the human body. It is only produced in significant amounts during pregnancy as it is made by the placenta. In pregnant women with multiple sclerosis (MS), estriol reduces the disease's symptoms noticeably, according to researchers at UCLA's Geffen Medical School.
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<b>*Molecular Weight</b>
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'''Mechanism of Action''': 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.
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288.38
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'''Indication''': Used as a test to determine the general health of an unborn fetus.
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<b>*Molecular Formula</b>
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'''KEGG Pathway'''(C05141,D00185)
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C<sub>1</sub><sub>8</sub>H<sub>2</sub><sub>4</sub>O<sub>3</sub>
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*Androgen and estrogen metabolism
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'''Target''' estrogen receptor (ER) agonist
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'''Activity''' Estrogen
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<b>*IUPAC NAME</b>
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{| border="1;width:100%; height:200px;style=text-align:center"
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|+'''List of PDB files having estriol as a Ligand:'''
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|-
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! style="background:brown; color:white" |MMDB ID
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! style="background:brown; color:white" |PDB ID
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! style="background:brown; color:white" |Reference
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|-
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|30668
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|1X8V
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|Podust LM, Yermalitskaya LV, Lepesheva GI, Podust VN, Dalmasso EA, Waterman MREstriol bound and ligand-free structures of sterol 14alpha-demethylaseStructure v12, p.1937-1945
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|-
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|}
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{| border="1;width:100%; height:200px;style=text-align:center"
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|+'''Physiochemical properties of Estriol:'''
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|-
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! style="background:brown; color:white" |Physical Property
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! style="background:brown; color:white" |Value
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! style="background:brown; color:white" |Units
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! style="background:brown; color:white" |Temp (deg C)
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! style="background:brown; color:white" |Source
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|-
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|Melting Point
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|282
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|deg C
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|  
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|EXP
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|-
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|log P (octanol-water)
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|2.45
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|(none)
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|  
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|EXP
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|-
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|Water Solubility
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|441
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|mg/L
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|25
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|EST
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|-
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|Vapor Pressure
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|1.97E-10
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|mm Hg
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|25
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|EST
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|-
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|Henry's Law Constant
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|1.33E-12
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|atm-m3/mole
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|25
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|EST
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|-
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|Atmospheric OH Rate Constant
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|1.29E-10
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|cm3/molecule-sec
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|25
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|EST
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|-
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|}
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{| border="1;width:100%; height:200px;style=text-align:center"
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|+'''Toxicity:'''
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|-
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! style="background:brown; color:white" |Organism
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! style="background:brown; color:white" |Test Type 
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! style="background:brown; color:white" |Route 
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! style="background:brown; color:white" |Reported Dose (Normalized Dose)
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! style="background:brown; color:white" |Effect
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! style="background:brown; color:white" |Source
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|-
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|rat
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|LD50
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|oral
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|> 2gm/kg (2000mg/kg)
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|  
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|Drugs in Japan Vol. -, Pg. 176, 1990.
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|}
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Levels of estriol in non-pregnant women do not change much after [[menopause]], and levels are not significantly different from levels in men.
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(8R,9S,13S,14S,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
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==Use in screening==
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<b>*Canonical Smiles</b>
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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]].
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If levels of "unconjugated estriol" are abnormally low in a pregnant woman, this may indicate a chrmosomal or congenital anomalies like [[Down's syndrome]] or [[Edward's syndrome]]. It is included as part of the [[triple test]] & [[quadrupole test]] for antenatal screening for fetal anomalies.
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CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
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Because many pathological conditions in a pregnant woman can cause deviations in estriol levels, these screenings are often seen as less definitive of fetal-placental health than [[non-stress testing]]. Conditions which can create [[false-positives]] and [[false-negatives]] in estriol testing for fetal distress include [[preeclampsia]], [[anemia]] and impaired [[kidney function]].<ref>{{cite book |title=Mosby's manual of Diagnostic and Laboratory Tests, 2nd Edition |first=Kathleen |last=Deska Pagana |coauthors=Pagana, Timothy J. |year=2002}}</ref>
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<b>*Isomeric Smiles</b>
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==References==
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C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)O
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<references/>
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{{med-stub}}
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{{Sex hormones}}
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==PhysioChemical Properties==
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[[Category:Estrogens]]
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<b>*Melting Point</b>
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282(EXP)
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<b>*LogP</b>
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2.45(EXP)
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<b>*Water Solubility</b>
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441(EST) at 25C
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==External Links==
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*[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5756]Pubchem
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*[http://www.rcsb.org/pdb/cgi/explore.cgi?pdbId=1X8V]]1X8V,
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*[http://www.genome.jp/dbget-bin/www_bget?compound+C05141]KEGG Compound
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*[http://www.genome.jp/dbget-bin/www_bget?drug+D00185]KEGG Drug
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*[http://www.hmdb.ca/metabolites/HMDB00153]Human Metabolome DataBase
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*[http://www.drugbank.ca/drugs/DB04573]Drugbank
 +
 
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[[Categories:Hormones]]

Revision as of 00:00, 15 January 2001


Contents

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.

General Properties

*Molecular Weight

288.38

*Molecular Formula

C18H24O3

*IUPAC NAME

(8R,9S,13S,14S,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol

*Canonical Smiles

CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O

*Isomeric Smiles

C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)O


PhysioChemical Properties

*Melting Point

282(EXP)

*LogP

2.45(EXP)

*Water Solubility

441(EST) at 25C

External Links

  • [1]Pubchem
  • [2]]1X8V,
  • [3]KEGG Compound
  • [4]KEGG Drug
  • [5]Human Metabolome DataBase
  • [6]Drugbank

Categories:Hormones

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