(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,13,14-triol

• ChemBase编号: 4141
• 分子式: C18H24O3
• 平均质量: 288.38136
• 单一同位素质量: 288.17254463
• SMILES: O[C@@H]1[C@@]2([C@H]([C@H]3[C@H](CC2)c2c(CC3)cc(O)cc2)C[C@H]1O)C
• Canonical SMILES: Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1C[C@H]([C@@H]2O)O)C
• InChI: InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1
• InChIKey: PROQIPRRNZUXQM-ZXXIGWHRSA-N

名称和登记号

名称

• IUPAC标准名: (1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,13,14-triol; (1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,13,14-triol; (1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,13,14-triol; (1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol
• IUPAC传统名: estriol
• 商标名: Deuslon-A; Estriel
• 别名: 1,3,5(10)-三烯-3β,16α,17β-三醇; 16,17-二羟甾醇; 雌激素三醇; 雌三醇; Oestriol; Estriol; (16α,17β)-Estra-1,3,5[10]-triene-3,16,17-triol; Acifemine; Colpogyn; Destriol; Ovesterin; Ovestin; Tricovex; Oestriol; (16alpha,17beta)-Oestra-1,3,5(10)-triene-3,16,17-triol; (16alpha,17beta)-estra-1,3,5(10)-triene-3,16,17-triol; 1,3,5(10)-Estratriene-3,16alpha,17beta-triol; 1,3,5-Estratriene-3beta,16alpha,17beta-triol; 1,3,5-Oestratriene-3beta,16alpha,17beta-triol; 16-alpha,17-beta-Estriol; 16-alpha,17-beta-Oestriol; 16-alpha-Hydroxyestradiol; 16-alpha-Hydroxyoestradiol; 16alpha,17beta-Estriol; 16alpha,17beta-Oestriol; 16alpha-Hydroxy-17beta-estradiol; 16alpha-Hydroxyoestradiol; 16alpha-hydroxyestradiol; 3,16-alpha,17-beta-Estriol; 3,16-alpha,17-beta-Oestriol; 3,16-alpha,17-beta-Trihydroxy-delta-1,3,5-estratriene; 3,16-alpha,17-beta-Trihydroxy-delta-1,3,5-oestratriene; 3,16-alpha,17-beta-Trihydroxyestra-1,3,5(10)-triene; 3,16-alpha,17-beta-Trihydroxyoestra-1,3,5(10)-triene; 3,16alpha,17beta-Estriol; 3,16alpha,17beta-Trihydroxy-1,3,5(10)-estratriene; 3,16alpha,17beta-Trihydroxy-delta-1,3,5-oestratriene; 3,16alpha,17beta-trihydroxy-Delta(1,3,5)-estratriene; ESL; Estra-1,3,5(10)-trien-3,16alpha,17beta-triol; Estra-1,3,5(10)-triene-3,16,17-triol; Estratriol; Estriolo [italian]; Oestra-1,3,5(10)-triene-3,16alpha,17beta-triol; Oestriolum; Ovestrion; Tridestrin; 1,3,5(10)-Estratriene-3,16,17-Triol; Estriol; 1,3,5(10)-Estratriene-3,16α,17β-triol; 16α-Hydroxyestradiol; 3,16α,17β-Trihydroxy-1,3,5(10)-estratriene

登记号

• CAS号: 50-27-1
• EC号: 200-022-2
• MDL号: MFCD00003691
• Beilstein号: 2508172
• PubChem SID: 46505881; 24894391; 24870296; 24894396; 160967573
• PubChem CID: 5756
• CHEBI ID: 27974
• ATC码: G03CA04; G03CC06
• CHEMBL: 193482
• Chemspider ID: 5553
• DrugBank ID: DB04573
• KEGG ID: C05141
• 医学主题词(MeSH): Estriol
• 美国药典/FDA物质标识码: FB33469R8E
• 维基百科标题: Estriol

理论计算性质

JChem

• Acid pKa: 10.326835
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): 2.6705914
• LogD (pH = 7.4): 2.6700869
• Log P: 2.6705978
• 摩尔折射率: 81.2662 cm^3
• 极化性: 31.925823 Å^3
• 极化表面积: 60.69 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: 2.54
• LOG S: -3.38
• 溶解度: 1.19e-01 g/l

分子性质

理化性质

• 溶解度: Alcohol; Chloroform; Dioxane; Ether; Pyridine
• 外观: White Solid
• 熔点: 280-282 °C; 280-282 °C(lit.); 282-283°C
• 比旋光度: [α]20/D +57±2°, c = 0.4% in dioxane; [α]20/D +62°, c = 1 in 95% ethanol
• 疏水性(logP): 2.45 [HANSCH,C ET AL. (1995)]

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: KG8225000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 60-61-40
• 安全公开号: 53-36/37-45
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H351-H360
• GHS警示性声明: P201-P281-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

• 相关基因信息: human ... SERPINA6(866)mouse ... Esr1(13982)rat ... Ar(24208)

产品相关信息

• 纯度: ≥97%; ≥97.0% (HPLC); 98%
• 级别: purum; VETRANAL™, analytical standard
• 成盐信息: Free Base
• 适用性: meets USP testing specifications
• 燃烧残渣: ≤0.1% (as SO4)
• 干燥失重: ≤0.5% loss on drying, 110 °C
• Empirical Formula (Hill Notation): C18H24O3

详细说明

MP Biomedicals - 05213780

MP Biomedicals Rare Chemical collection

DrugBank - DB04573

• Drug Groups: approved
• Description: A hydroxylated metabolite of estradiol or estrone that has a hydroxyl group at C3-beta, 16-alpha, and 17-beta position. Estriol is a major urinary estrogen. During pregnancy, large amount of estriol is produced by the placenta. Isomers with inversion of the hydroxyl group or groups are called epiestriol. Though estriol is used as part of the primarily North American phenomenon of bioidentical hormone replacement therapy, it is not approved for use by the FDA or Health Canada. It is however available in the United States by prescription filled only by compounding pharmacies. It has also been approved and marketed throughout Europe and Asia for approximately 40 years for the treatment of post-menopausal hot flashes.
• Indication: Used as a test to determine the general health of an unborn fetus.
• Pharmacology: Estriol (also oestriol) is one of the three main estrogens produced by the human body. It is only produced in significant amounts during pregnancy as it is made by the placenta. In pregnant women with multiple sclerosis (MS), estriol reduces the disease's symptoms noticeably, according to researchers at UCLA's Geffen Medical School.
• Toxicity: ORAL (LD50): Acute: >2000 mg/kg [Rat].
• Affected Organisms: Humans and other mammals
• References: Soldan SS, Alvarez Retuerto AI, Sicotte NL, Voskuhl RR: Immune modulation in multiple sclerosis patients treated with the pregnancy hormone estriol. J Immunol. 2003 Dec 1;171(11):6267-74. [Pubmed] ; [Trimesta]
• External Links: Wikipedia

Selleck Chemicals - S2466

Research Area

• Description: Endocrinology

Biological Activity

• Description: Estriol is an antagonist of the G-protein coupled estrogen receptor in estrogen receptor-negative breast cancer cells.
• Targets: GPR30
• In Vitro: MTT assays using G-1 shows that, in SkBr3 cells, the proliferative effect induced by 100 nM G-1 is abolished in the presence of 1 μM estriol which acts as an antagonist of GPR30-dependent pathway. ^[1]A cell-free transcription assay demonstrates that the antiestrogenic activity exhibited by estriol is because of interferring with estradiol-induced positive cooperative binding and receptor dimerization, binding of hER complexes to ERE, as well as reducing estradiol-dependent transcription in a dose-dependent manner. ^[2]A recent study shows that estrogen (estrone, estradiol, and estriol) inhibits Alzheimer's disease-associated low-order Aβ oligomer formation, and among them, estriol shows the strongest in vitro activity. ^[3]
• In Vivo: In mPTEN+/- mice, estriol treatments resulted in a 187.54% gain in the relative ratio of uterine wet weight to body weight; estriol also increases the ratio to 176.88% in wild-type mice. ^[4]Estriol treatment (20 mg/kg ip), in vivo, sensitizes Kupffer cells to LPS via mechanisms dependent on an increase in CD14 by elevated portal blood endotoxin caused by increased gut permeability in rats; while one-half of the rats given estriol intraperitoneally 24 hours before an injection of a sublethal dose of LPS (5 mg/kg) died within 24 hours. ^[5]
• Clinical Trials: Estriol is currently under investigation in Phase I clinical trials; dealing with the vaginal environment of pre-menopausal women.

Protocol

• Protocol: Cell Assay ^[1]
• Cell Lines: SkBr3 cells
• Concentrations: ~100 nM
• Incubation Time: 6 days
• Methods: For the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, cells are cultured in plastic 96-well plates under 200 μL of growth medium and at an initial density of 10,000 cells per well. Cells are washed once they have attached and further incubated in medium containing 2.5% charcoal-stripped FBS with the indicated treatment. The medium is changed every 2 days (with treatment). Where applicable, 200 ng of the indicated plasmids are transfected every 2 days before treatments using Fugene6 Reagent, as recommended by the manufacturer. Following 6 days of incubation, the assay mixture (10μL per well) containing 1mg/mL 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) is added to each well and incubated at 37 ?C for 4 h in a 5% CO₂ atmosphere. The yellow tetrazolium MTT, reduced by metabolically active cells, results in intracellular purple formazan, which is released after overnight incubation with 200 μL 1% sodium dodecyl sulfate in 0.01N HCL and quantified spectrophotometrically by reading absorbance at 570nm using an enzyme-linked immunosorbent assay plate reader.
• Protocol: Animal Study ^[4]
• Animal Models: mPTEN+/- and wild-type mice
• Formulation: Estriol is dissolved in ethanol and corn oil.
• Doses: 4 μg/g/day
• Administration: Administrated via s.c.

References

• References: [1] Lappano R, et al. Mol Cell Endocrinol. 2010, 320(1-2), 162-170.
• References: [2] Melamed M, et al. Endocrinol. 1997, 11(12), 1868-1878.
• References: [3] Morinaga A, et al. Exp Neurol. 2011, 228(2), 298-302.
• References: [4] Begum M, et al. Lab Invest. 2006,86(3), 286-296.
• References: [5] Hewitt SC, et al. Environ Health Perspect. 2011, 119(1), 63-70.

Sigma Aldrich - E1253

Biochem/physiol Actions
Estriol is a metabolite of 17β-estradiol with much lower biological activity. It is the primary estrogen found in the urine. Large quantities of estriol and estrone are produced by the placenta during pregnancy. These are also the primary estrogens produced by adipose tissue in men and in post-menopausal women.
包装
1 g in poly bottle
100, 500 mg in poly bottle

Sigma Aldrich - 285803

包装
1 g in glass bottle

Sigma Aldrich - 46565

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - E888960

A metabolite of Estradiol. An estrogenic metabolite considerably less potent than the hormone Estradiol.

参考文献

• Soldan SS, Alvarez Retuerto AI, Sicotte NL, Voskuhl RR: Immune modulation in multiple sclerosis patients treated with the pregnancy hormone estriol. J Immunol. 2003 Dec 1;171(11):6267-74. Pubmed
• Trimesta
• Lappano R, et al. Mol Cell Endocrinol. 2010, 320(1-2), 162-170.
• Melamed M, et al. Endocrinol. 1997, 11(12), 1868-1878.
• Morinaga A, et al. Exp Neurol. 2011, 228(2), 298-302.
• Begum M, et al. Lab Invest. 2006,86(3), 286-296.
• Hewitt SC, et al. Environ Health Perspect. 2011, 119(1), 63-70.
• Marrian, et al.: Biochem. J., 23,1090 (1929)
• Huffman, et al.: J. Biol. Chem., 169, 167 (1929)