雄甾烷-3,7,17-三醇 | 19316-62-2

• 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
• 中文名称: 雄甾烷-3,7,17-三醇
• 英文名称: 5-alpha-Androstane-3-beta,7-alpha,17-beta-triol
• 英文别名: 5α-androstane-3β,7α,17β-triol；7α,3β,17β-androstanetriol；3β,7α,17β-Trihydroxy-5α-androstan；5alpha-Androstane-3beta,7alpha,17beta-triol；(3S,5R,7R,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,17-triol
• CAS: 19316-62-2
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: UFGLFVVFQFFPSV-LKBCLYITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 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：

  5alpha-雄烷二醇 在 氧气 作用下， 生成 表雄酮 、 雄甾烷-3,7,17-三醇 、 雄诺龙 、 雄烯二酮 、 5a-雄甾烷二酮 、 雄甾烷-3,6,17-三醇 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  The identification and characterization of the c19o3 steroid metabolites of 5α-androstane-3β, 17β-diol produced by the canine prostate: 5α-androstane-3β, 6α, 17β-triol and 5α-androstane-3β, 7α, 17β-triol

  摘要：

  This study has identified the polar metabolites of 5 alpha-androstane-3 beta-17 beta-diol(3 beta-diol) produced by the canine prostate. The major metabolite is 5 alpha-androstane-3 beta,7 alpha,17 beta-triol(7 alpha-triol) accounting for approximately 80% of the total polar metabolites of 3 beta-diol. The remaining 20% is accounted for exclusively by another triol, 5 alpha-androstane-3 beta,6 alpha,17 beta-triol(6 alpha-triol). This study has also characterized two enzymatic hydroxylase responsible for respective triol formation: 5 alpha-androstane-3 beta,17 beta-diol 6 alpha-hydroxylase(6 alpha-hydroxylase) and 5 alpha-androstane-3 beta,17 beta-diol 7 alpha-hydroxylase(7 alpha-hydroxylase). Both of these irreversible hydroxylases are located in the particulate fraction of the prostate and can utilize either NADH or NADPH as cofactor. Several in vitro steroid inhibitors of these hydroxylases were identified including cholesterol, estradiol and diethylstilbestrol. Neither of the hydroxylases were found to be decreased by castration (3 months) when expressed as activity/DNA. Using a variety of C19 androstane substrates, 6 alpha- and 7 alpha-triol were found to be major components of the total 3 beta-hydroxy-5 alpha-androstane metabolites produced by the canine prostate.

  DOI：

  10.1016/0039-128x(80)90099-9

文献信息

• The identification and characterization of the c19o3 steroid metabolites of 5α-androstane-3β, 17β-diol produced by the canine prostate: 5α-androstane-3β, 6α, 17β-triol and 5α-androstane-3β, 7α, 17β-triol
  作者：John T. Isaacs、Ian R. McDermott、Donald S. Coffey

  DOI：10.1016/0039-128x(80)90099-9

  日期：1980.2

  This study has identified the polar metabolites of 5 alpha-androstane-3 beta-17 beta-diol(3 beta-diol) produced by the canine prostate. The major metabolite is 5 alpha-androstane-3 beta,7 alpha,17 beta-triol(7 alpha-triol) accounting for approximately 80% of the total polar metabolites of 3 beta-diol. The remaining 20% is accounted for exclusively by another triol, 5 alpha-androstane-3 beta,6 alpha,17 beta-triol(6 alpha-triol). This study has also characterized two enzymatic hydroxylase responsible for respective triol formation: 5 alpha-androstane-3 beta,17 beta-diol 6 alpha-hydroxylase(6 alpha-hydroxylase) and 5 alpha-androstane-3 beta,17 beta-diol 7 alpha-hydroxylase(7 alpha-hydroxylase). Both of these irreversible hydroxylases are located in the particulate fraction of the prostate and can utilize either NADH or NADPH as cofactor. Several in vitro steroid inhibitors of these hydroxylases were identified including cholesterol, estradiol and diethylstilbestrol. Neither of the hydroxylases were found to be decreased by castration (3 months) when expressed as activity/DNA. Using a variety of C19 androstane substrates, 6 alpha- and 7 alpha-triol were found to be major components of the total 3 beta-hydroxy-5 alpha-androstane metabolites produced by the canine prostate.