Estrone

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'''Estrone(oestrone)'''
 
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'''Pubchem(5870)'''
 
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An aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone, a major mammalian estrogen. It is converted from ANDROSTENEDIONE directly, or from TESTOSTERONE via ESTRADIOL. In humans, it is produced primarily by the cyclic ovaries, PLACENTA, and the ADIPOSE TISSUE of men and postmenopausal women.
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==Description==
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An aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone, a   major mammalian estrogen. It is converted from ANDROSTENEDIONE   directly, or from TESTOSTERONE via ESTRADIOL. In humans, it is   produced primarily by the cyclic ovaries, PLACENTA, and the ADIPOSE   TISSUE of men and postmenopausal women.
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==General Properties==
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'''KEGG Pathway'''(C00468,D00067)
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<b>*Molecular Weight</b>
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*Androgen and estrogen metabolism
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Activity Estrogen
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270.37
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NEXTBIO
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<b>*Molecular Formula</b>
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'''Drug Type:'''  Small Molecule; Approved
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C<sub>1</sub><sub>8</sub>H<sub>2</sub><sub>2</sub>O<sub>2</sub>
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'''Pharmacology:''' Estrone, a synthetically prepared or naturally occurring steroidal estrogen obtained from pregnant equine urine, is the primary circulating estrogen after menopause. Estrone is naturally derived from the peripheral conversion of androstenedione by an aromatase enzyme found in adipose tissues and is converted to estradiol in peripheral tissues. Estropipate is piperazine-stabilized estrone sulfate. Estrone, and estropipate are used to treat abnormalities related to gonadotropin hormone dysfunction, vasomotor symptoms, atrophic vaginitis, and vulvar atrophy associated with menopause, and for the prevention of osteoporosis due to estrogen deficiency.
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<b>*IUPAC NAME</b>
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'''Mechanism of Action:''' Estrogens enter the cells of responsive tissues (e.g., female organs, breasts, hypothalamus, pituitary) where they interact with a protein receptor, estrogen receptors, subsequently increasing the rate of synthesis of DNA, RNA, and some proteins. 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.
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(8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
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Indication: For management of Menopausal and postmenopausal disorders
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'''Half Life:''' 19 hours
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<b>*Canonical Smiles</b>
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Lipinski’s “Rule of Five” Prediction for a Compound’s ABSORPTION OR PERMEABILITY PROPERTIES
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CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)O
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4 GOOD
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3 INDETERMINATE
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<b>*Isomeric Smiles</b>
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2 INDETERMINATE
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1 INDETERMINATE
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C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O
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0 POOR
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{| border="1;width:100%; height:200px;style=text-align:center"
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|+'''Table I:'''
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==PhysioChemical Properties==
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|-
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! style="background:brown; color:white" |Physical Property
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<b>*Melting Point</b>
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! style="background:brown; color:white" |Value
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! style="background:brown; color:white" |Units
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260.2(EXP)
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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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<b>*LogP</b>
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|-
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|Melting Point
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3.13(EXP)
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|260.2
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|deg C
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<b>*Water Solubility</b>
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| 
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|EXP
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30(EXP) at 25C
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|-
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|Boiling Point
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==External Links==
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|154
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*[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5870]Pubchem
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|deg C
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*[http://www.genome.jp/dbget-bin/www_bget?compound+C00468]KEGG Compound
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| 
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*[http://www.genome.jp/dbget-bin/www_bget?drug+D00067]KEGG Drug
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|EXP
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*[http://www.hmdb.ca/metabolites/HMDB00145]Human Metabolome DataBase
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|-
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*[http://www.drugbank.ca/drugs/DB00655]Drugbank
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|log P (octanol-water)
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|3.13
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[[Categories:Hormones]]
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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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|30
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|mg/L
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|25
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|EXP
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|-
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|Vapor Pressure
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|1.42E-07
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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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|3.80E-10
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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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|1.26E-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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Revision as of 00:00, 15 January 2001


Contents

Description

An aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone, a major mammalian estrogen. It is converted from ANDROSTENEDIONE directly, or from TESTOSTERONE via ESTRADIOL. In humans, it is produced primarily by the cyclic ovaries, PLACENTA, and the ADIPOSE TISSUE of men and postmenopausal women.

General Properties

*Molecular Weight

270.37

*Molecular Formula

C18H22O2

*IUPAC NAME

(8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one

*Canonical Smiles

CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)O

*Isomeric Smiles

C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O


PhysioChemical Properties

*Melting Point

260.2(EXP)

*LogP

3.13(EXP)

*Water Solubility

30(EXP) at 25C

External Links

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

Categories:Hormones

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