CAS 53-16-7|estrone|Estrone|Oestrone|(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-one|Estronum [INN-Latin]|Estrogenic Substance|Folisan|Oestrin|Fol...

基本信息

化学结构

分子式

C₁₈H₂₂O₂

分子量

270.36608

精确质量

270.16197994

电荷

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

Canonic Smiles

Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C

Isomeric Smiles

O=C1[C@@]2([C@H]([C@H]3[C@H](CC2)c2c(CC3)cc(O)cc2)CC1)C

计算属性

JChem

LogD (pH = 7.4)

4.31

LogD (pH = 5.5)

4.31

Log P

4.31

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

10.33

极化表面积

37.30

极化性

31.28

摩尔折射率

79.08

LOG S

-4.18

数据来源

名称和标识

别名

EstroneOestroneESTRONE, U.S.P.3-羟基雌甾-1,3,5(10)-三烯-17-酮雌(三烯酚)酮3-Hydroxy-1,3,5(10)-estratrien-17-one雌酚酮Folliculin雌酮Estrone1,3,5(10)-Estratrien-3-ol-17-oneCristallovar3-Hydroxy-17-keto-estra-1,3,5-trieneCrystogenCrinovaryl(+)-EstroneWynestronAquacrine3-Hydroxyestra-1,3,5(10)-trien-17-oneWAY 164397OestrinOxohydroxyoestrinMenformonFollicular hormone(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-oneProgynonestronefollicular hormoneestroneoestrone3-Hydroxy-1,3,5(10)-estratrien-17-onefolliculinEstrone

IUPAC标准名

(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-one (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 (3aS,3bR,9bS,11aS)-7-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-one

IUPAC传统名

estrone (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one

商标名

FollidrinPenncap MTokokinFemestrone Inj.Estrona [Spanish]SolliculinTheelinEstronUndenFollestrolFolliculinPerlatanEstrone [Usan:Inn]ThelestrinOestrone [Steroidal Oestrogens]MenagenOestroperosFollicunodisEndofolliculinaEstrugenoneEstrogenic SubstanceKetohydroxyestrinDisynformonKetohydroxy-EstratrieneFolipexCrystogenWynestronFolisanFollestrineFollicular HormoneAquacrineEsteroneEstrone-AFolliculine BenzoateEstrolSinafid M-48HormovarineMenformonCrinovarylOestrinOestroneOestronumEstrinDestroneThynestronFemestrone InjectionKetophydroxyestrinWynestronpencap MFolliculineGlandubolinHormestrinEstronaKolponMestronaqOvifollinKetohydroxyoestrinEstrona [INN-Spanish]GSS 33HormofollinOestroformKestroneMenformon ACristallovarFemidynThelykininOVEXHiestroneEstrusolFermidynEstronum [INN-Latin]EstrovarinKetodestrinFolikrin

API名称

Estrone

国际非专利药品(INN)

estrone

名称和标识

数据登录号

化合物性质

药理学性质

半衰期

19 hours

蛋白结合率

>95%

相关基因信息

human ... ESR1(2099), ESR2(2100), ESRRA(2101), ESRRB(2103), HSD17B1(3292), SERPINA6(866)mouse ... Esr1(13982)rat ... Esr1(24890)

生物活性机理

Estrogen

化合物性质

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB00655

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

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]

MP Biomedicals

05214691

MP Biomedicals Rare Chemical collection

Wikipedia

Estrone

Sigma Aldrich

E9750

Biochem/physiol Actions
Estrone is a luteolytic estrogen produced by the corpus luteum.
包装
1, 5, 25 g in glass bottle
500 mg in glass bottle

46573

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

TRC

E889050

A metabolite of 17β-Estradiol.

ChEBI

CHEBI:17263

A 17-oxo steroid that is estra-1,3,5(10)-triene substituted by an hydroxy group at position 3 and an oxo group at position 17.

描述信息

参考文献

PubChem文献

数据源提供

• http://en.wikipedia.org/wiki/Estrone

• Goodman-Gruen, D., et al.: J. Clin. Endocrinol. Metab., 81, 2999 (1983)

• Both, D., et al.: Anal. Profiles Drug Subs., 12, 135 (1983)

• Busetta, B. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1972, 274, 153, (cryst struct)

• Posner, G.H. et al., Tetrahedron, 1981, 37, 3921, (synth)

• Both, D., Anal. Profiles Drug Subst., 1983, 12, 135, (rev)

• Barlaam, B. et al., Tet. Lett., 1991, 32, 623, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 589C, (nmr)

• Kuo, C.H. et al., Chem. Ind. (London), 1966, 1340, (synth)

• Crabb, P. et al., Can. J. Chem., 1968, 46, 349, (14 synth, uv, ir)

• IARC Monog., 1979, 21, 343, (tox, rev)

• Quinkert, G. et al., Annalen, 1981, 2335, (synth)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4875; 4883

• Caspi, E. et al., Chem. Comm., 1989, 1302, (biosynth)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1183; 1192

• Hiraga, K. et al., Chem. Comm., 1969, 1013, (synth)

• Wittstruck, T.A. et al., J.O.C., 1973, 38, 1542, (cmr)

• Birch, A.J. et al., Aust. J. Chem., 1970, 23, 547, (synth)

• Crispin, D.J. et al., J.C.S.(C), 1970, 10, (synth)

• Sergeev, P.V. et al., Zh. Fiz. Khim., 1973, 47, 1643, (ms)

• Cohen, N. et al., J.O.C., 1975, 40, 681, (synth)

• Kametani, T. et al., J.A.C.S., 1976, 98, 3378; 1977, 99, 3461, (synth)

• Danishefsky, S. et al., J.A.C.S., 1976, 98, 4975, (synth)

• Duax, W.L. et al., Acta Cryst. B, 1979, 35, 2656, (cryst struct)

• Hutchinson, J.H. et al., Can. J. Chem., 1987, 65, 1, (synth)

• Taber, D.F. et al., J.O.C., 1987, 52, 28, (synth)

• Takano, S. et al., Tet. Lett., 1992, 33, 1909, (synth)

• Tanaka, K. et al., Org. Lett., 2000, 1915-1917, (synth)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1055D, (ir)

• Heftmann, E. et al., Phytochemistry, 1966, 5, 231; 1337, (isol)

• Ziegler, F.E. et al., Tet. Lett., 1981, 1179, (synth)

• Zepter, R., J. Prakt. Chem., 1971, 313, 1139, (synth, uv, pmr)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EDV000; EDV600

• Rufer, C. et al., Annalen, 1967, 705, 211, (synth)

• Sugahara, T. et al., Tet. Lett., 1996, 37, 7403, (synth)

• Smales, C.M. et al., Acta Cryst. C, 1997, 53, 1082-1084, (cryst struct)

• Douglas, G.H. et al., J.C.S., 1963, 5072, (synth, ir)

• Nicolaou, K.C. et al., J.O.C., 1980, 45, 1403, (synth)

• Grieco, P.A. et al., J.O.C., 1980, 45, 2247, (synth)

• Sunder, N.M. et al., J.C.S. Perkin 1, 1990, 1331, (synth)

• Subba Rao, G.S.R. et al., Aust. J. Chem., 1992, 45, 187, (synth)

• Nicolaou, K.C. et al., Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996, 153, (bibl, synth)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC标准名

IUPAC传统名

estrone (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one

商标名

API名称

Estrone

国际非专利药品(INN)

estrone

描述信息

DrugBank

DB00655

Drug Groups

approved

Description

Indication

For management of perimenopausal and postmenopausal symptoms.

Pharmacology

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Absorption

43%

Half Life

19 hours

Protein Binding

> 95%

References

External Links

• [Wikipedia]

Selleck Chemicals

S1665

MP Biomedicals

05214691

MP Biomedicals Rare Chemical collection

Wikipedia

Estrone

Sigma Aldrich

E9750

Biochem/physiol Actions
Estrone is a luteolytic estrogen produced by the corpus luteum.
包装
1, 5, 25 g in glass bottle
500 mg in glass bottle

46573

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

TRC

E889050

A metabolite of 17β-Estradiol.

ChEBI

CHEBI:17263

A 17-oxo steroid that is estra-1,3,5(10)-triene substituted by an hydroxy group at position 3 and an oxo group at position 17.

参考文献

PubChem文献

数据源提供

• http://en.wikipedia.org/wiki/Estrone

• Goodman-Gruen, D., et al.: J. Clin. Endocrinol. Metab., 81, 2999 (1983)

• Both, D., et al.: Anal. Profiles Drug Subs., 12, 135 (1983)

• Busetta, B. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1972, 274, 153, (cryst struct)

• Posner, G.H. et al., Tetrahedron, 1981, 37, 3921, (synth)

• Both, D., Anal. Profiles Drug Subst., 1983, 12, 135, (rev)

• Barlaam, B. et al., Tet. Lett., 1991, 32, 623, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 589C, (nmr)

• Kuo, C.H. et al., Chem. Ind. (London), 1966, 1340, (synth)

• Crabb, P. et al., Can. J. Chem., 1968, 46, 349, (14 synth, uv, ir)

• IARC Monog., 1979, 21, 343, (tox, rev)

• Quinkert, G. et al., Annalen, 1981, 2335, (synth)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4875; 4883

• Caspi, E. et al., Chem. Comm., 1989, 1302, (biosynth)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1183; 1192

• Hiraga, K. et al., Chem. Comm., 1969, 1013, (synth)

• Wittstruck, T.A. et al., J.O.C., 1973, 38, 1542, (cmr)

• Birch, A.J. et al., Aust. J. Chem., 1970, 23, 547, (synth)

• Crispin, D.J. et al., J.C.S.(C), 1970, 10, (synth)

• Sergeev, P.V. et al., Zh. Fiz. Khim., 1973, 47, 1643, (ms)

• Cohen, N. et al., J.O.C., 1975, 40, 681, (synth)

• Kametani, T. et al., J.A.C.S., 1976, 98, 3378; 1977, 99, 3461, (synth)

• Danishefsky, S. et al., J.A.C.S., 1976, 98, 4975, (synth)

• Duax, W.L. et al., Acta Cryst. B, 1979, 35, 2656, (cryst struct)

• Hutchinson, J.H. et al., Can. J. Chem., 1987, 65, 1, (synth)

• Taber, D.F. et al., J.O.C., 1987, 52, 28, (synth)

• Takano, S. et al., Tet. Lett., 1992, 33, 1909, (synth)

• Tanaka, K. et al., Org. Lett., 2000, 1915-1917, (synth)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1055D, (ir)

• Heftmann, E. et al., Phytochemistry, 1966, 5, 231; 1337, (isol)

• Ziegler, F.E. et al., Tet. Lett., 1981, 1179, (synth)

• Zepter, R., J. Prakt. Chem., 1971, 313, 1139, (synth, uv, pmr)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EDV000; EDV600

• Rufer, C. et al., Annalen, 1967, 705, 211, (synth)

• Sugahara, T. et al., Tet. Lett., 1996, 37, 7403, (synth)

• Smales, C.M. et al., Acta Cryst. C, 1997, 53, 1082-1084, (cryst struct)

• Douglas, G.H. et al., J.C.S., 1963, 5072, (synth, ir)

• Nicolaou, K.C. et al., J.O.C., 1980, 45, 1403, (synth)

• Grieco, P.A. et al., J.O.C., 1980, 45, 2247, (synth)

• Sunder, N.M. et al., J.C.S. Perkin 1, 1990, 1331, (synth)

• Subba Rao, G.S.R. et al., Aust. J. Chem., 1992, 45, 187, (synth)

• Nicolaou, K.C. et al., Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996, 153, (bibl, synth)

生物活性

PubChem BioAssay

化合物性质

药理学性质

半衰期

19 hours

蛋白结合率

>95%

化合物信息

ID:537