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53-16-7 molecular structure
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(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

ChemBase ID: 537
Molecular Formular: C18H22O2
Molecular Mass: 270.36608
Monoisotopic Mass: 270.16197994
SMILES and InChIs

SMILES:
O=C1[C@@]2([C@H]([C@H]3[C@H](CC2)c2c(CC3)cc(O)cc2)CC1)C
Canonical SMILES:
Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C
InChI:
InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1
InChIKey:
DNXHEGUUPJUMQT-CBZIJGRNSA-N

Cite this record

CBID:537 http://www.chembase.cn/molecule-537.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-14-one
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-trien-14-one
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-one
IUPAC Traditional name
estrone
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-trien-14-one
Brand Name
Aquacrine
Crinovaryl
Cristallovar
Crystogen
Destrone
Disynformon
Endofolliculina
Esterone
Estrin
Estrogenic Substance
Estrol
Estron
Estrona
Estrona [INN-Spanish]
Estrona [Spanish]
Estrone [Usan:Inn]
Estrone-A
Estronum [INN-Latin]
Estrovarin
Estrugenone
Estrusol
Femestrone Inj.
Femestrone Injection
Femidyn
Fermidyn
Folikrin
Folipex
Folisan
Follestrine
Follestrol
Follicular Hormone
Folliculin
Folliculine
Folliculine Benzoate
Follicunodis
Follidrin
GSS 33
Glandubolin
Hiestrone
Hormestrin
Hormofollin
Hormovarine
Kestrone
Ketodestrin
Ketohydroxy-Estratriene
Ketohydroxyestrin
Ketohydroxyoestrin
Ketophydroxyestrin
Kolpon
Menagen
Menformon
Menformon A
Mestronaq
OVEX
Oestrin
Oestroform
Oestrone
Oestrone [Steroidal Oestrogens]
Oestronum
Oestroperos
Ovifollin
Penncap M
Perlatan
Sinafid M-48
Solliculin
Theelin
Thelestrin
Thelykinin
Thynestron
Tokokin
Unden
Wynestron
Wynestronpencap M
Synonyms
Estrone
1,3,5(10)-Estratrien-3-ol-17-one
3-Hydroxy-1,3,5(10)-estratrien-17-one
Folliculin
Estrone
3-Hydroxyestra-1,3,5(10)-trien-17-one
(+)-Estrone
3-Hydroxy-17-keto-estra-1,3,5-triene
Aquacrine
Crinovaryl
Cristallovar
Crystogen
WAY 164397
Wynestron
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
Follicular hormone
Menformon
Oestrin
Oxohydroxyoestrin
Progynon
ESTRONE, U.S.P.
Oestrone
3-羟基雌甾-1,3,5(10)-三烯-17-酮
雌(三烯酚)酮
雌酮
雌酚酮
CAS Number
53-16-7
EC Number
200-164-5
MDL Number
MFCD00003620
Beilstein Number
1915077
PubChem SID
24278427
24870303
160964000
24894399
46505916
PubChem CID
5870
CHEBI ID
17263
ATC CODE
G03CA07
G03CC04
CHEMBL
1405
Chemspider ID
5660
DrugBank ID
DB00655
IUPHAR ligand ID
2818
KEGG ID
D00067
Unique Ingredient Identifier
2DI9HA706A
Wikipedia Title
Estrone

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.326958  H Acceptors
H Donor LogD (pH = 5.5) 4.3090224 
LogD (pH = 7.4) 4.3085184  Log P 4.309029 
Molar Refractivity 79.0824 cm3 Polarizability 30.7614 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.03  LOG S -4.84 
Solubility (Water) 3.94e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
3 g/100mL expand Show data source
Chloroform (Sparingly) expand Show data source
Apperance
White to Off-White Crystalline Solid expand Show data source
Melting Point
254.5°C (490.1°F) expand Show data source
254-256°C expand Show data source
258-260 °C(lit.) expand Show data source
Hydrophobicity(logP)
3.382 expand Show data source
3.6 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
RTECS
KG8575000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
45-60-61 expand Show data source
Safety Statements
53-45 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H350-H360 expand Show data source
GHS Precautionary statements
P201-P308 + P313 expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Eyeshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
Half Life
19 hours expand Show data source
Protein Bound
>95% expand Show data source
Gene Information
human ... ESR1(2099), ESR2(2100), ESRRA(2101), ESRRB(2103), HSD17B1(3292), SERPINA6(866)mouse ... Esr1(13982)rat ... Esr1(24890) expand Show data source
Mechanism of Action
Estrogen expand Show data source
Purity
≥99% expand Show data source
95% expand Show data source
Grade
USP expand Show data source
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Suitability
meets USP testing specifications expand Show data source
Biological Source
Obt. from human pregnancy urine and from pregnant mares' urine. Also a trace constit. of plant tissues, e.g. seeds of date (Phoenix dactylifera) and pomegranate (Punica granatum) expand Show data source
Application(s)
Used therapeutically in combination with other natural estrogens expand Show data source
Empirical Formula (Hill Notation)
C18H22O2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 05214691 external link
MP Biomedicals Rare Chemical collection
DrugBank - DB00655 external link
Item Information
Drug Groups approved
Description Estrone, one of the major mammalian estrogens, is an aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone. It is produced in vivo from androstenedione or from testosterone via estradiol. It is produced primarily in the ovaries, placenta, and in peripheral tissues (especially adipose tissue) through conversion of adrostenedione. Estrone may be further metabolized to 16-alpha-hydroxyestrone, which may be reduced to estriol by estradiol dehydrogenase.
Indication For management of perimenopausal and postmenopausal symptoms.
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. The estrogenic potency of estrone is one third that of estradiol. 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.
Toxicity Symptoms of overdose include nausea and vomiting. Estrogen related side effects include nausea, breast tenderness, fluid retention and edema, headaches and/or migraines, chloasma and poor contact lens fit. Estrogen hormone deficiency is associated with breakthrough bleeding, hypomenorrhea, irritability, depression and menopausal symptoms. Withdrawal bleeds may occur in females.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
Absorption 43%
Half Life 19 hours
Protein Binding > 95%
References
Miyoshi Y, Tanji Y, Taguchi T, Tamaki Y, Noguchi S: Association of serum estrone levels with estrogen receptor-positive breast cancer risk in postmenopausal Japanese women. Clin Cancer Res. 2003 Jun;9(6):2229-33. [Pubmed]
Kajta M, Lason W, Bien E, Marszal M: Neuroprotective effects of estrone on NMDA-induced toxicity in primary cultures of rat cortical neurons are independent of estrogen receptors. Pol J Pharmacol. 2002 Nov-Dec;54(6):727-9. [Pubmed]
External Links
Wikipedia
Selleck Chemicals - S1665 external link
Research Area: Endocrinology
Biological Activity:
Estrone is an estrogenic hormone secreted by the ovary as well as adipose tissue. Estrone is one of the three estrogens, which also include estriol and estradiol. Estrone is the least abundant of the three hormones, estradiol is always in the reproductive female body, and estriol is abundant primarily during pregnancy. Estrone is relevant to health and disease states because of its conversion to estrone sulfate, a long-lived derivative. Estrone sulfate acts as a reservoir that can be converted as needed to the more active estradiol. [1]
Sigma Aldrich - E9750 external link
Biochem/physiol Actions
Estrone is a luteolytic estrogen produced by the corpus luteum.
Packaging
1, 5, 25 g in glass bottle
500 mg in glass bottle
Sigma Aldrich - 46573 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Toronto Research Chemicals - E889050 external link
A metabolite of 17β-Estradiol.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Miyoshi Y, Tanji Y, Taguchi T, Tamaki Y, Noguchi S: Association of serum estrone levels with estrogen receptor-positive breast cancer risk in postmenopausal Japanese women. Clin Cancer Res. 2003 Jun;9(6):2229-33. Pubmed
  • • Kajta M, Lason W, Bien E, Marszal M: Neuroprotective effects of estrone on NMDA-induced toxicity in primary cultures of rat cortical neurons are independent of estrogen receptors. Pol J Pharmacol. 2002 Nov-Dec;54(6):727-9. Pubmed
  • • http://en.wikipedia.org/wiki/Estrone
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