依托孕烯杂质 | 215252-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 依托孕烯杂质
• 英文名称: 13-ethyl-11-methylene-6β,17β-dihydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one
• 英文别名: 13β-ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-6β,17β-diol-3-one；6beta-Hydroxy-3-Ketodesogestrel；6b-Hydroxy Etonogestrel；(6R,8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-6,17-dihydroxy-11-methylidene-2,6,7,8,9,10,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 215252-94-1
• 化学式: C₂₂H₂₈O₃
• 分子量: 340.463
• InChiKey: UXUSJLZOAVPWDL-HLJOZBTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  依托孕烯 在 Cunninghamella blakesleeana 作用下， 以 甲醇 为溶剂， 反应 288.0h， 生成 依托孕烯杂质 、 13-ethyl-11-methylene-15α,17β-dihydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one 、 13-ethyl-6β,17β-dihydroxy-18,19-dinor-11-spirooxiran-17α-pregn-4-en-20-yn-3-one 、 13-ethyl-17β-hydroxy-18,19-dinor-11β-spirooxiran-17α-pregn-4-en-20-yn-3-one 、 13-ethyl-11-methylene-10β,17β-dihydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one
  参考文献：
  名称：

  Microbial transformation of contraceptive drug etonogestrel into new metabolites with Cunninghamella blakesleeana and Cunninghamella echinulata

  摘要：

  Biotransformation of a steroidal contraceptive drug, etonogestrel (1), (13-ethyl-17 beta-hydroxy-11-methylene-18,19-dinor-17 alpha-pregn-4-en-20-yn-3-one) was investigated with Cunninghamella blakesleeana and C. echinulata. Five metabolites 2-6 were obtained on incubation of 1 with Cunninghamella blakesleeana, and three metabolites, 2, 4, and 6 were isolated from the transformation of 1 with C echinulata. Among them, metabolites 2-4 were identified as new compounds. Their structures were deduced as 6 beta-hydroxy-11,22-epoxy-etonogestrel (2), 11,22-epoxy-etonogestrel (3), 10 beta-hydroxy-etonogestrel (4), 6 beta-hydroxy-etonogestrel (5), and 14 alpha-hydroxy-etonogestrel (6). Compounds 1-6 were evaluated for various biological activities. Interestingly, compound 5 was found to be active against beta-glucuronidase enzyme with IC50 value of 13.97 +/- 0.12 mu M, in comparison to standard compound, D-saccharic acid 1,4-lactone (IC50 = 45.75 +/- 2.16 mu M). Intestinal bacteria produce beta-glucuronidase. Increased activity of beta-glucuronidase is responsible for the hydrolyses of glucuronic acid conjugates of estrogen and other toxic substances in the colon, which plays a key role in the etiology of colon cancer. Inhibition of beta-glucoronidase enzyme therefore has a therapeutic significance. Compounds 1-6 were also found to be non cytotoxic against 3T3 mouse fibroblast cell lines. (C) 2016 Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2016.08.003