(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编号: 537
• 分子式: C18H22O2
• 平均质量: 270.36608
• 单一同位素质量: 270.16197994
• 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

名称和登记号

名称

• IUPAC标准名: (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[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-one; (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]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传统名: estrone; (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-14-one
• 商标名: 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
• 别名: 3-羟基雌甾-1,3,5(10)-三烯-17-酮; 雌(三烯酚)酮; 雌酮; 雌酚酮; 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

登记号

• CAS号: 53-16-7
• EC号: 200-164-5
• MDL号: MFCD00003620
• Beilstein号: 1915077
• PubChem SID: 46505916; 160964000; 24894399; 24278427; 24870303
• PubChem CID: 5870
• CHEBI ID: 17263
• ATC码: G03CA07; G03CC04
• CHEMBL: 1405
• Chemspider ID: 5660
• DrugBank ID: DB00655
• IUPHAR配体索引: 2818
• KEGG ID: D00067
• 美国药典/FDA物质标识码: 2DI9HA706A
• 维基百科标题: Estrone

理论计算性质

JChem

• Acid pKa: 10.326958
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 4.3090224
• LogD (pH = 7.4): 4.3085184
• Log P: 4.309029
• 摩尔折射率: 79.0824 cm^3
• 极化性: 30.7614 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.03
• LOG S: -4.84
• 溶解度: 3.94e-03 g/l

分子性质

理化性质

• 溶解度: 3 g/100mL; Chloroform (Sparingly)
• 外观: White to Off-White Crystalline Solid
• 熔点: 254.5°C (490.1°F); 254-256°C; 258-260 °C(lit.)
• 疏水性(logP): 3.382; 3.6

安全信息

• 保存条件: -20°C; Refrigerator
• RTECS编号: KG8575000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 45-60-61
• 安全公开号: 53-45
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H350-H360
• GHS警示性声明: P201-P308 + P313
• 个人保护装置: 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; Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

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

产品相关信息

• 纯度: ≥99%; 95%
• 级别: USP; VETRANAL™, analytical standard
• 成盐信息: Free Base
• 适用性: meets USP testing specifications
• 生物来源: 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)
• 应用领域: Used therapeutically in combination with other natural estrogens
• Empirical Formula (Hill Notation): C18H22O2

详细说明

MP Biomedicals - 05214691

MP Biomedicals Rare Chemical collection

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]

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

Sigma Aldrich - 46573

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - E889050

A metabolite of 17β-Estradiol.

参考文献

• 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
• Both, D., et al.: Anal. Profiles Drug Subs., 12, 135 (1983)
• Goodman-Gruen, D., et al.: J. Clin. Endocrinol. Metab., 81, 2999 (1983)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1055D, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 589C, (nmr)
• Douglas, G.H. et al., J.C.S., 1963, 5072, (synth, ir)
• Kuo, C.H. et al., Chem. Ind. (London), 1966, 1340, (synth)
• Heftmann, E. et al., Phytochemistry, 1966, 5, 231; 1337, (isol)
• Rufer, C. et al., Annalen, 1967, 705, 211, (synth)
• Crabb, P. et al., Can. J. Chem., 1968, 46, 349, (14 synth, uv, ir)
• Hiraga, K. et al., Chem. Comm., 1969, 1013, (synth)
• Birch, A.J. et al., Aust. J. Chem., 1970, 23, 547, (synth)
• Crispin, D.J. et al., J.C.S.(C), 1970, 10, (synth)
• Zepter, R., J. Prakt. Chem., 1971, 313, 1139, (synth, uv, pmr)
• Busetta, B. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1972, 274, 153, (cryst struct)
• Wittstruck, T.A. et al., J.O.C., 1973, 38, 1542, (cmr)
• 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)
• IARC Monog., 1979, 21, 343, (tox, rev)
• Nicolaou, K.C. et al., J.O.C., 1980, 45, 1403, (synth)
• Grieco, P.A. et al., J.O.C., 1980, 45, 2247, (synth)
• Quinkert, G. et al., Annalen, 1981, 2335, (synth)
• Ziegler, F.E. et al., Tet. Lett., 1981, 1179, (synth)
• Posner, G.H. et al., Tetrahedron, 1981, 37, 3921, (synth)
• Both, D., Anal. Profiles Drug Subst., 1983, 12, 135, (rev)
• Hutchinson, J.H. et al., Can. J. Chem., 1987, 65, 1, (synth)
• Taber, D.F. et al., J.O.C., 1987, 52, 28, (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)
• Sunder, N.M. et al., J.C.S. Perkin 1, 1990, 1331, (synth)
• Barlaam, B. et al., Tet. Lett., 1991, 32, 623, (synth)
• Subba Rao, G.S.R. et al., Aust. J. Chem., 1992, 45, 187, (synth)
• Takano, S. et al., Tet. Lett., 1992, 33, 1909, (synth)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1183; 1192
• Nicolaou, K.C. et al., Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996, 153, (bibl, 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)
• Tanaka, K. et al., Org. Lett., 2000, 1915-1917, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EDV000; EDV600