4-[(3R,4S)-4-(4-hydroxyphenyl)hexan-3-yl]phenol

• ChemBase编号: 5561
• 分子式: C18H22O2
• 平均质量: 270.36608
• 单一同位素质量: 270.16197994
• SMILES: c1c(ccc(c1)[C@H](CC)[C@H](CC)c1ccc(O)cc1)O
• Canonical SMILES: CC[C@H]([C@@H](c1ccc(cc1)O)CC)c1ccc(cc1)O
• InChI: InChI=1S/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3/t17-,18+
• InChIKey: PBBGSZCBWVPOOL-HDICACEKSA-N

名称和登记号

名称

• IUPAC标准名: 4-[(3R,4S)-4-(4-hydroxyphenyl)hexan-3-yl]phenol; 4-[(3S,4R)-4-(4-hydroxyphenyl)hexan-3-yl]phenol
• IUPAC传统名: hexestrol; 4-[(3S,4R)-4-(4-hydroxyphenyl)hexan-3-yl]phenol
• 别名: 4,4′-(1,2-二乙基亚乙基)二苯酚; 二羟二苯己烷; 六羟春情素; 己烷雌酚; 4,4′-(1,2-Diethylethylene)diphenol; meso-3,4-Bis(4-hydroxyphenyl)hexane; Dihydrodiethylstilbestrol; Bibenzyl; Cycloestrol; Dihydro-stilbestro; Hexestrol; 4-[(1R,2S)-1-ethyl-2-(4-hydroxyphenyl)butyl]phenol; Hexestrol

登记号

• CAS号: 84-16-2
• EC号: 201-518-1
• MDL号: MFCD00068996
• Beilstein号: 3209460
• PubChem SID: 24870032; 99444402; 24895805; 160968989
• PubChem CID: 192197

理论计算性质

JChem

• Acid pKa: 9.926587
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 5.3656373
• LogD (pH = 7.4): 5.36437
• Log P: 5.3656535
• 摩尔折射率: 82.6572 cm^3
• 极化性: 32.048504 Å^3
• 极化表面积: 40.46 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 4.98
• LOG S: -4.29
• 溶解度: 1.39e-02 g/l

分子性质

安全信息

• 保存条件: -20°C
• RTECS编号: SL0560850
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 2
• 危险公开号: 45
• 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
• 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

药理学性质

• 作用靶点: Estrogen receptor
• 相关基因信息: human ... ESR1(2099)rat ... Esr1(24890)

产品相关信息

• 纯度: ≥98%
• 级别: analytical standard; VETRANAL™, analytical standard
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C18H22O2

详细说明

DrugBank - DB07931

Drug information: experimental

Selleck Chemicals - S2473

Research Area

• Description: Cancer

Biological Activity

• Description: Hexestrol binds to Erα and ERβ with EC50 of 0.07 nM and 0.175 nM, respectively.
• Targets: ERα; ERβ
• IC50: 0.07 nM (EC50); 0.175 nM (EC50) ^[1]
• In Vitro: Hexestrol binds to ERα with EC50 of 0.07 nM and to ERβ with EC50 of 0.175 nM. ^[1] Hexestrol inhibits activity of AKR1B13 with IC50 of 3.2 μM. ^[2] Hexestrol inhibits the d-galactose dehydrogenase activity of thermophilus aldose 1-dehydrogenase with IC50 of 0.063 mM. ^[3] Hexestrol inhibits the dehydrogenase activity of AKR1C20 towards 10 μM 4-androsten-3α-o1-17-one with IC50 values of 2.7 μM. ^[4] Hexestrol inhibits 17HSD5 with IC50 of 30 μM, and inhibits TBER1 with IC50 of 0.8 μM. ^[5] Hexestrol reacts with DNA through the catechol quinone, thus can be a carcinogen. ^[6]
• In Vivo: Hexestrol administered intraperitoneally at dose of 6 mg/kg may decrease ovulation in mice, as evident by smaller ovaries and decreased luteal bodies and oocytes. ^[7]
• Features: Much higher ERβ binding selectivity than Erα

Protocol

• Protocol: Kinase Assay ^[1]
• Estrogen Receptor Binding Affinity Assays: Relative binding affinities are determined by a competitive radiometric binding assay, using 10 nM [^3H]estradiol as tracer, and purified full-length human ERα and ERβ. Incubations are for 18–24 h at 0 °C, then the receptor-ligand complexes are absorbed onto hydroxyapatite and unbound ligand is washed away. The binding affinities are expressed as relative binding affinity (RBA) values, with the RBA of estradiol set to 100. The values given are the average ± range or SD of two or more independent determinations. Hexestrol is tested as racemate.
• Protocol: Animal Study ^[7]
• Animal Models: adult mice aged 90-120 days
• Formulation: Saline
• Doses: 3 mg/kg and 6 mg/kg
• Administration: administered intraperitoneally once daily for 30 days

References

• References: [1] Waibel M, et al. Eur J Med Chem, 2009, 44(9), 3412-3424.
• References: [2] Endo S, et al. Chem Biol Interact, 2009, 178(1-3), 151-157.
• References: [3] Asada Y, et al. Chem Biol Interact. 2009, 178(1-3), 117-126.
• References: [4] Matsumoto K, et al. Biol Pharm Bull, 2006, 29(3), 539-542.
• References: [5] Ishikura S, et al. J Biochem, 2006, 139(6), 1053-1063.
• References: [6] Ishikura S, et al. Ann N Y Acad Sci, 2004, 1028, 247-257.

Sigma Aldrich - 46320

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - H7753

Biochem/physiol Actions
The carcinogen hexestrol is a nonsteroidal synthetic estrogen. Metabolic activation of hexestrol to its quinone, which reacts with DNA to form analogous depurinating adducts, may be a primary critical event leading to oncogenic mutations and cancer initiation.
Linkage
己烯雌酚的还原类似物。

参考文献

• Waibel M, et al. Eur J Med Chem, 2009, 44(9), 3412-3424.
• Endo S, et al. Chem Biol Interact, 2009, 178(1-3), 151-157.
• Asada Y, et al. Chem Biol Interact. 2009, 178(1-3), 117-126.
• Matsumoto K, et al. Biol Pharm Bull, 2006, 29(3), 539-542.
• Ishikura S, et al. J Biochem, 2006, 139(6), 1053-1063.
• Ishikura S, et al. Ann N Y Acad Sci, 2004, 1028, 247-257.