17α-methyl-5β-androstane-1β,3α,17β-triol | 88458-53-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 17α-methyl-5β-androstane-1β,3α,17β-triol
• 英文别名: (1R,3S,5R,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-1,3,17-triol
• CAS: 88458-53-1
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: YDFXHPQKSNAZPH-CWXOLEPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  17β-羟基-17α-甲基-5β-雄烷-3-酮 在 1,2-丙二醇 作用下， 以89.5%的产率得到17α-methyl-5β-androstane-3α,17β-diol
  参考文献：
  名称：

  Metabolism of 17α-methyl-5β-dihydrotestosterone in the rabbit

  摘要：

  17 alpha-Methyl-5 beta-androstane-3 alpha,17 beta-diol together with the hydroxylated metabolites 17 alpha-methyl-5 beta-androstane-1 beta,3 alpha,17 beta-triol, 17 alpha-methyl-5 beta-androstane-3 alpha,12 beta,17 beta-triol, 17 alpha-methyl-5 beta-androstane-3 alpha,16 alpha,17 beta-triol and 17 alpha-methyl-5 beta-androstane-3 alpha,16 beta,17 beta-triol were isolated and identified in the urine of rabbits orally dosed with 17 alpha-methyl-5 beta-dihydrotestosterone. Biotransformations differ from the 5 alpha-series where hydroxylation occurred at C-6 and C-15. In both series, the C-3 equatorial epimer was the major urinary excretion product among the non-hydroxylated metabolites. The 5 beta-compound was more resistant to metabolic hydroxylation than the 5 alpha-compound. No evidence for epimerization at the C-17 position was observed.

  DOI：

  10.1016/0039-128x(83)90089-2