17α-methyl-2α,11β,17β-trihydroxyestr-4-en-3-one | 1428370-35-7

• 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-2α,11β,17β-trihydroxyestr-4-en-3-one
• 英文别名: (2R,8S,9S,10R,11S,13S,14S,17S)-2,11,17-trihydroxy-13,17-dimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 1428370-35-7
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: HHDQLLDJWYLXOJ-WSZMCMCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲基诺龙 在 Macrophomina phaseolina KUCC 730 作用下， 以 水 为溶剂， 反应 192.0h， 以0.018%的产率得到17α-methyl-6β,17β-dihydroxyestr-4-en-3-one
  参考文献：
  名称：

  New metabolites from fungal biotransformation of an oral contraceptive agent: Methyloestrenolone

  摘要：

  Fungal cell cultures were used for the first time for the biotransformation of methyloestrenolone (1), an oral contraceptive. Fermentation of I with Macrophomina phaseolina, Aspergillus niger, Gibberella fujikuroi, and Cunninghamella echinulata produced eleven metabolites 2-12, six of which 2-5, 11 and 12 were found to be new. These metabolites were resulted from the hydroxylation at C-1, C-2, C-6, C-10, C-1 1, and C-17 alpha-CH3, as well as aromatization of ring A of the steroidal skeleton of substrate 1. The transformed products were identified as 17 alpha-methyl-6 beta,17 beta-dihydroxyestr-4-en-3-one (2), 17 alpha-(hydroxymethyl)-11 beta,17 beta-dihydroxyestr-4-en-3-one (3), 17 alpha-methyl-2 alpha,11 beta,17 beta-trihydroxyestr-4-en-3-one (4), 17 alpha-methyl-1 beta,17 beta-dihydroxyestr-4-en-3-one (5), 17 alpha-methyl-11 alpha,17 beta-dihydroxyestr-4-en-3-one (6), 17 alpha-methyl-11 beta,17 beta-dihydroxyestr-4-en-3-one (7), 17 alpha-methyl-10 beta,17 beta-dihydroxyestr-4-en-3 -one (8), 17 alpha-( hydroxymethyl)-17 beta-hydroxyestr-4-en-3-one (9), 17 alpha-methylestr-1,3,5(10)-trien-3,17 B-diol (10), 17 beta-methyl-3,17 beta-dihydroxyestr-1,3,5(10)-trien-6-one (11), and 17 alpha-methyl-6 beta,10 beta,17 beta-trihydroxyestr-4-en-3-one (C). 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.01.002

文献信息

• New metabolites from fungal biotransformation of an oral contraceptive agent: Methyloestrenolone
  作者：Salman Zafar、Marium Bibi、Sammer Yousuf、M. Iqbal Choudhary

  DOI：10.1016/j.steroids.2013.01.002

  日期：2013.4

  Fungal cell cultures were used for the first time for the biotransformation of methyloestrenolone (1), an oral contraceptive. Fermentation of I with Macrophomina phaseolina, Aspergillus niger, Gibberella fujikuroi, and Cunninghamella echinulata produced eleven metabolites 2-12, six of which 2-5, 11 and 12 were found to be new. These metabolites were resulted from the hydroxylation at C-1, C-2, C-6, C-10, C-1 1, and C-17 alpha-CH3, as well as aromatization of ring A of the steroidal skeleton of substrate 1. The transformed products were identified as 17 alpha-methyl-6 beta,17 beta-dihydroxyestr-4-en-3-one (2), 17 alpha-(hydroxymethyl)-11 beta,17 beta-dihydroxyestr-4-en-3-one (3), 17 alpha-methyl-2 alpha,11 beta,17 beta-trihydroxyestr-4-en-3-one (4), 17 alpha-methyl-1 beta,17 beta-dihydroxyestr-4-en-3-one (5), 17 alpha-methyl-11 alpha,17 beta-dihydroxyestr-4-en-3-one (6), 17 alpha-methyl-11 beta,17 beta-dihydroxyestr-4-en-3-one (7), 17 alpha-methyl-10 beta,17 beta-dihydroxyestr-4-en-3 -one (8), 17 alpha-( hydroxymethyl)-17 beta-hydroxyestr-4-en-3-one (9), 17 alpha-methylestr-1,3,5(10)-trien-3,17 B-diol (10), 17 beta-methyl-3,17 beta-dihydroxyestr-1,3,5(10)-trien-6-one (11), and 17 alpha-methyl-6 beta,10 beta,17 beta-trihydroxyestr-4-en-3-one (C). 2013 Elsevier Inc. All rights reserved.