14-deoxypoststerone | 1360460-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 14-deoxypoststerone
• 英文别名: alpha-14-deoxy-poststerone；[14α-H]14-deoxypoststerone；2beta,3beta-Dihydroxy-5beta-pregn-7-ene-6,20-dione；(2S,3R,5R,9R,10R,13S,14R,17S)-17-acetyl-2,3-dihydroxy-10,13-dimethyl-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one
• CAS: 1360460-98-5
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: OGEJBBPFFLOZKJ-KMSCCEEJSA-N

物化性质

• 沸点：
  508.0±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2β,3β,5β,14xi)-2,3,14-三羟基孕-7-烯-6,20-二酮 在 溶剂黄146 、 锌 作用下， 生成 14-deoxypoststerone 、 [14β-H]14-deoxypoststerone
  参考文献：
  名称：

  The metabolism of 20-hydroxyecdysone in mice: Relevance to pharmacological effects and gene switch applications of ecdysteroids

  摘要：

  Ecdysteroids exert many pharmacological effects in mammals (including humans), most of which appear beneficial, but their mechanism faction is far from understood. Whether they act directly and/or after the formation of metabolites is still an open question. The need to investigate this question has gained extra impetus because of the recent development of ecdysteroid-based gene-therapy systems for mammals.In order to investigate the metabolic fate of ecdysteroids in mice, [1 alpha,2 alpha-(3)H]20-hydroxyecdysone was prepared and injected intraperitoneally to mice. Their excretory products (urine + faeces) were collected and the different tritiated metabolites were isolated and identified. The pattern of ecdysteroid metabolites is very complex, but no conjugates were found, in contrast to the classical fate of the (less polar) endogenous vertebrate steroid hormones. Primary reactions involve dehydroxylation at C-14 and side-chain cleavage between C-20 and C-22, thereby yielding 14-deoxy-20-hydroxyecdysone, poststerone and 14-deoxypoststerone. These metabolites then undergo several reactions of reduction involving, in particular, the 6-keto-group.A novel major metabolite has been identified as 2 beta,3 beta,6 alpha,22R,25-pentahydroxy-5 beta-cholest-8(14)-ene. The formation of this and the other major metabolites is discussed in relation to the various effects of ecdysteroids already demonstrated on vertebrates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2011.03.016