(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: 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

NAMES AND DATABASE IDS

Names

• 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[8.7.0.0^2,^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 Traditional name: 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
• 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

Database IDs

• CAS Number: 53-16-7
• EC Number: 200-164-5
• MDL Number: MFCD00003620
• Beilstein Number: 1915077
• PubChem SID: 24894399; 46505916; 24870303; 160964000; 24278427
• PubChem CID: 5870
• CHEBI ID: 17263
• ATC CODE: G03CC04; G03CA07
• CHEMBL: 1405
• Chemspider ID: 5660
• DrugBank ID: DB00655
• IUPHAR ligand ID: 2818
• KEGG ID: D00067
• Unique Ingredient Identifier: 2DI9HA706A
• Wikipedia Title: Estrone

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.326958
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.3090224
• LogD (pH = 7.4): 4.3085184
• Log P: 4.309029
• Molar Refractivity: 79.0824 cm^3
• Polarizability: 30.7614 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.03
• LOG S: -4.84
• Solubility (Water): 3.94e-03 g/l

PROPERTIES

Physical Property

• Solubility: 3 g/100mL; Chloroform (Sparingly)
• Apperance: White to Off-White Crystalline Solid
• Melting Point: 254.5°C (490.1°F); 254-256°C; 258-260 °C(lit.)
• Hydrophobicity(logP): 3.382; 3.6

Safety Information

• Storage Condition: -20°C; Refrigerator
• RTECS: KG8575000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-60-61
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H350-H360
• GHS Precautionary statements: P201-P308 + P313
• 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; Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

Pharmacology Properties

• Half Life: 19 hours
• Protein Bound: >95%
• Gene Information: human ... ESR1(2099), ESR2(2100), ESRRA(2101), ESRRB(2103), HSD17B1(3292), SERPINA6(866)mouse ... Esr1(13982)rat ... Esr1(24890)
• Mechanism of Action: Estrogen

Product Information

• Purity: ≥99%; 95%
• Grade: USP; VETRANAL™, analytical standard
• Salt Data: Free Base
• Suitability: meets USP testing specifications
• 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)
• Application(s): Used therapeutically in combination with other natural estrogens
• Empirical Formula (Hill Notation): C18H22O2

DETAILS

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.
Packaging
1, 5, 25 g in glass bottle
500 mg in glass bottle

Sigma Aldrich - 46573

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - E889050

A metabolite of 17β-Estradiol.

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
• 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