1α-methyl-11α,17β-dihydroxy-5α-androstan-3-one | 854508-22-8

• 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: 1α-methyl-11α,17β-dihydroxy-5α-androstan-3-one
• 英文别名: 1alpha-Methyl-11alpha,17beta-dihydroxy-5alpha-androstan-3-one；(1S,5S,8S,9S,10S,11R,13S,14S,17S)-11,17-dihydroxy-1,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 854508-22-8
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: HJKZMXWXFSAARE-FPBMTUGXSA-N

物化性质

• 沸点：
  460.2±45.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲氢睾酮 在 Cunninghamella blakesleeana 作用下， 以 水 、 丙酮 为溶剂， 反应 216.0h， 以5 mg的产率得到1α-methyl-1β,11β,17β-trihydroxy-5α-androstan-3-one
  参考文献：
  名称：

  Biotransformation of androgenic steroid mesterolone with Cunninghamella blakesleeana and Macrophomina phaseolina

  摘要：

  Fermentation of mesterolone (1) with Cunninghamella blakesleeana yielded four new metabolites, 1 alpha-methyl-1 beta,11 beta,17 beta-trihydroxy-5 alpha-androstan-3-one (2), 1 alpha-methyl-7 alpha,11 beta,17 beta-trihydroxy-5 alpha-androstan-3-one (3), 1 alpha-methyl-1 beta,6 alpha,17 beta-trihydroxy-5 alpha-androstan-3-one (4) and 1 alpha-methyl-1 beta,11 alpha,17 beta-trihydroxy-5 alpha-androstan-3-one (5), along with three known metabolites, 1 alpha-methyl-11 alpha,17 beta-dihydroxy-5 alpha-androstan-3-one (6), 1 alpha-methyl-6 alpha,17 beta-dihydroxy-5 alpha-androstan-3-one (7) and 1 alpha-methyl-7 alpha,17 beta-dihydroxy-5 alpha-androstan-3-one (8). Biotransformation of 1 with Macrophomina phaseolina also yielded a new metabolite, 1 alpha-methyl, 17 beta-hydroxy-5 alpha-androstan-3,6-dione (9). The isolated metabolites were subjected to various in vitro biological assays, such as anti-cancer, inhibition of alpha-glucosidase, and phosphodiesterase-5 enzymes and oxidative brust. However, no significant results were observed. This is the first report of biotransformation of 1 with C. blakesleeana and M. phaseolina. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.01.001