inokosterone | 88980-54-5

• 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: inokosterone
• 英文别名: (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,7-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• CAS: 88980-54-5
• 化学式: C₂₇H₄₄O₇
• 分子量: 480.642
• InChiKey: JQNVCUBPURTQPQ-XDWLXSIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  34
• 可旋转键数：
  6
• 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

• 作为反应物：
  描述：

  inokosterone 在 吡啶 、 sodium periodate 作用下， 生成 2β-Acetoxy-3β,14α-dihydroxy-5β-pregn-7-en-6,20-dion
  参考文献：
  名称：

  Absolute configuration of inokosterone, an insect-moulting substance from

  摘要：

  DOI：

  10.1016/s0040-4039(00)76160-0
• 作为产物：
  描述：

  (2S,3R,5R,9R,10R,13R,14S,17S)-17-((2R,3R)-2,3-dihydroxy-6-methyl-7-((tetrahydro-2H-pyran-2-yl)oxy)heptan-2-yl)-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one 在 盐酸 作用下， 生成 inokosterone
  参考文献：
  名称：

  Inokosterone，一种来自牛膝的昆虫变态物质：绝对构型和合成

  摘要：

  从牛膝（Achyranthes fauriei）（A菜科）中分离出来的植物蜕皮激素Inokosterone已部分乙酰化，得到2,26-二乙酸酯（4），该酯已转化为5-乙酰氧基-4-甲基戊酸甲酯（7），没有明显的[α]。D和2β-乙酰氧基-3β，14α-二羟基-5β-pregn-7-烯-6,20-二酮（8）。化学和物理的研究在C-20和C-22已示出的配置是- [R。因此，已将Inokosterone推定为（25 R，22 R）-2β，3β，14α，20,22,26-六羟基-5β-胆甾-7-en-6-1（1的C-25差向异构体的混合物）。合成模型化合物后，已通过（20 R）-合成了（20 R，22 R）-3β，20,22,26-四羟基-5α-胆甾烷（23）和inokosterone的C-25异构体混合物。通过Grignard反应与4-（四氢呋喃-2-酰氧基）-3-甲基丁炔基溴化镁进行格氏反应

  DOI：

  10.1016/0040-4020(76)80160-3

文献信息

• Transformation of 20-hydroxyecdysone to inokosterone
  作者：Rimma G. Savchenko、Ruslan V. Shafikov、Svetlana R. Afonkina、Viktor N. Odinokov

  DOI：10.1070/mc2006v016n02abeh002258

  日期：2006.1

  Delta(24)/Delta(25)-Derivatives of 20-hydroxyecdysone were hydroborated by sodium borohydride in the presence of CuCl followed by oxidation of organoboron intermediate and deblocking of hydroxyl groups to synthesise the zoo- and phytoecdysteroid inokosterone.
• 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.