14-Epi-20-hydroxyecdysone

• 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: 14-Epi-20-hydroxyecdysone
• 英文别名: (2S,3R,5R,9R,10R,13R,14R,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• 化学式: C₂₇H₄₄O₇
• 分子量: 480.642
• InChiKey: NKDFYOWSKOHCCO-MQVWFXNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  138
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  蜕皮激素 以 水 为溶剂， 反应 4.0h， 以1 mg的产率得到(1R,5R,7R,8S,10R,11R,14S,15S)-7,8-dihydroxy-10-methyl-15-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]pentacyclo[12.3.1.01,14.02,11.05,10]octadec-2-en-4-one
  参考文献：
  名称：

  Photochemical transformation of 20-hydroxyecdysone: production of monomeric and dimeric ecdysteroid analogues

  摘要：

  Structural modification of 20-hydroxyecdysone (20E) based on photochemical trans formation yielded dimeric ecdysteroid 7alphaH,7'alphaH-bis-[(20R,22R)-20,3p,2beta,3beta,20,22,25-pentahydroxy-5beta-cholest-8(14)-en-6-one-7-yl] as a main product. Its structure was determined by detailed NMR analysis. Furthermore, two new monomeric analogues: 14-epi-20-hydroxyecdysone and 14-deoxy-14,18-cyclo-20-hydroxyecdysone were identified in addition to the earlier described 14-deoxy and t4-hydroperoxy derivatives of 20E. Formation of the specific and so far unique ecdysteroid dimer has not been observed in earlier photo-transformation studies. The transformed dimeric analogue of 20-hydroxyecdysone retained the high agonistic activity on the ecdysone receptor in the B-II-bioassay compared with the original 20E. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00140-4