(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-triene-5,6,14-triol

• ChemBase编号: 156057
• 分子式: C18H24O3
• 平均质量: 288.38136
• 单一同位素质量: 288.17254463
• SMILES: C[C@]12CC[C@@H]3c4ccc(c(c4CC[C@H]3[C@@H]1CC[C@@H]2O)O)O
• Canonical SMILES: O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2O)O
• InChI: InChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1
• InChIKey: QOZFCKXEVSGWGS-ZHIYBZGJSA-N

名称和登记号

名称

• IUPAC标准名: (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,6,14-triol
• IUPAC传统名: 4-hydroxyestradiol
• 别名: 1,3,5(10)-Estratriene-3,4,17β-triol; 4-Hydroxyestradiol; 4-Hydroxy-17β-estradiol; (17β)-Estra-1,3,5(10)-triene-3,4,17-triol; 4-Hydroxyestradiol

登记号

• CAS号: 5976-61-4
• MDL号: MFCD00063335
• PubChem SID: 162250195; 24895648
• PubChem CID: 5282360

理论计算性质

• Acid pKa: 9.694773
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): 3.4419084
• LogD (pH = 7.4): 3.439752
• Log P: 3.441936
• 摩尔折射率: 81.8856 cm^3
• 极化性: 31.912842 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

分子性质

理化性质

• 溶解度: Methanol
• 外观: Light Brown Solid
• 熔点: >210°C (dec.)

安全信息

• 保存条件: -20°C Freezer, Under Inert Atmosphere
• RTECS编号: KG7676000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 40
• 安全公开号: 22-36
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H351
• GHS警示性声明: P281
• 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
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... ESR1(2099)rat ... Ar(24208)

产品相关信息

• Empirical Formula (Hill Notation): C18H24O3

详细说明

Sigma Aldrich - H4637

Biochem/physiol Actions
4-Hydroxyestradiol, an metabolite of estradiol, forms adducts with adenine (N3) and guanine (N7) by depurinating sites in DNA of cultured human breast epithelial cells. This effect may play an important role in malignant transformation of these cells.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H4637.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - H941895

A metabolite of Estradiol.

参考文献

• Bucala, R., et al.: J. Clin. Endocrinol. Metab., 60, 841 (1985)
• Telang, N., et al.: Anticancer Res., et al.: 11, 1021 (1985)
• Seeger, H., et al.: Med. Sci. Res., 26, 481 (1985)
• Bolton, J., et al.: Chem. Res. Toxicol., 13, 135 (1985)