20-hydroxyecdyson-26-oic acid | 86583-58-6

• 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: 20-hydroxyecdyson-26-oic acid
• 英文别名: (5R,6R)-2,5,6-trihydroxy-2-methyl-6-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanoic acid
• CAS: 86583-58-6
• 化学式: C₂₇H₄₂O₉
• 分子量: 510.625
• InChiKey: CBVIQTRBPLDFEH-KIZORZRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  176
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  松甾酮A 在 air 、 葡萄糖 、 epidermis of premolt crab Carcinus maenas L 、 penicillin G 、 三羟甲基氨基甲烷 、 苯基硫脲 作用下， 以 水 为溶剂， 反应 48.0h， 生成 蜕皮激素 、 inokosterone 、 25-deoxy-20-hydroxyecdyson-26-oic acid 、 20-hydroxyecdyson-26-oic acid 、 20,26-二羟基蜕皮激素 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Ecdysteroid metabolism in a crab : Carcinus maenas l.

  摘要：

  Ponasterone A (25-deoxy-20-hydroxyecdysone) and 20-hydroxyecdysone were the major ecdysteroids detected in crab hemolymph, although some ecdysone was also present. The metabolism of ponasterone A was examined in intermolt and premolt crabs either by injecting the radiolabeled hormone or by incubating tissues in its presence. Metabolites were extracted from the surrounding seawater and from tissues and separated by high-performance liquid chromatography. Ponasterone A metabolism proceeds through (1) C-25 and C-26 hydroxylation, followed by formation of inactivation products via oxidation of the terminal alcoholic group to a carboxylic residue, (2) conjugation, (3) "binding" to very polar compounds and (4) side-chain scission. The conversion of ponasterone A into 20-hydroxyecdysone, inokosterone (25-deoxy-20, 26-dihydroxyecdysone), 20, 26-dihydroxyecdysone and ecdysonoic acids, as well as the formation of conjugates and of very polar compounds, occurs in various tissues. These metabolites were excreted by both intermolt and premolt crabs.

  DOI：

  10.1016/0039-128x(84)90043-6

文献信息

• Ecdysteroid metabolism in a crab : Carcinus maenas l.
  作者：Fabienne Lachaise、René Lafont

  DOI：10.1016/0039-128x(84)90043-6

  日期：1984.3

  Ponasterone A (25-deoxy-20-hydroxyecdysone) and 20-hydroxyecdysone were the major ecdysteroids detected in crab hemolymph, although some ecdysone was also present. The metabolism of ponasterone A was examined in intermolt and premolt crabs either by injecting the radiolabeled hormone or by incubating tissues in its presence. Metabolites were extracted from the surrounding seawater and from tissues and separated by high-performance liquid chromatography. Ponasterone A metabolism proceeds through (1) C-25 and C-26 hydroxylation, followed by formation of inactivation products via oxidation of the terminal alcoholic group to a carboxylic residue, (2) conjugation, (3) "binding" to very polar compounds and (4) side-chain scission. The conversion of ponasterone A into 20-hydroxyecdysone, inokosterone (25-deoxy-20, 26-dihydroxyecdysone), 20, 26-dihydroxyecdysone and ecdysonoic acids, as well as the formation of conjugates and of very polar compounds, occurs in various tissues. These metabolites were excreted by both intermolt and premolt crabs.