11β,21-dihydroxy-3,20-dioxo-5α-pregnan-18-al | 6251-71-4

• 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: 11β,21-dihydroxy-3,20-dioxo-5α-pregnan-18-al
• 英文别名: 5alpha-Dihydroaldosterone；(5S,8S,9S,10S,11S,13R,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-13-carbaldehyde
• CAS: 6251-71-4
• 化学式: C₂₁H₃₀O₅
• 分子量: 362.466
• InChiKey: IIBOWSHDTFRYKU-WHIQTFJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11β,21-dihydroxy-3,20-dioxo-5α-pregnan-18-al 在 咪唑 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 3β,5α-tetrahydroaldosterone 21-TBDMS ether
  参考文献：
  名称：

  Kirk, David N.; Rajagopalan, Maruthiandan S., Journal of the Chemical Society. Perkin transactions I, 1987, p. 1343 - 1346

  摘要：

  DOI：
• 作为产物：
  描述：

  醛固酮 在 Tris-HCl buffer 、 adult male Sprague-Dawley rat liver microsomes 、 还原型辅酶II(NADPH)四钠盐 、 magnesium chloride 作用下， 反应 0.08h， 生成 11β,21-dihydroxy-3,20-dioxo-5α-pregnan-18-al 、 5β-dihydroaldosterone 、 tetrahydroaldosterone 、 3α,11β,21-trihydroxy-20-oxo-5α-pregnan-18-al 、 3β,11β,21-trihydroxy-20-oxo-5α-pregnan-18-al 、 3β,11β,21-trihydroxy-20-oxo-5β-pregnan-18-al 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  The effects of adrenal and gonadal steroids and K+-canrenoate on the metabolism of aldosterone by rat liver microsomes

  摘要：

  The synthesis of polar aldosterone metabolites by rat liver microsomes at physiological concentrations of aldosterone (21.5 nM), was markedly inhibited by progesterone, testosterone, corticosterone, K+-canrenoate and estradiol-17 beta. In contrast, corticosterone and estradiol-17 beta significantly increased the synthesis of reduced aldosterone metabolites by 8- and 15-fold respectively, the majority of which were 5 alpha-reduced products of aldosterone. In experiments at higher substrate (aldosterone) concentrations (20-200 microM) the synthesis of ring A-reduced aldosterone metabolites by liver microsomes followed Michaelis-Menten kinetics with a Km[app] for aldosterone of 160 microM and Vmax[app] of 12.2 nmoles/mg protein/5 min. In these experiments progesterone, testosterone and K+-canrenoate all competitively inhibited the synthesis of reduced metabolites with inhibition constants (Ki [app]) of 70, 85 and 55 microM respectively; however, corticosterone did not. In contrast, estradiol-17 beta increased the rate of synthesis of reduced products by 40%, lowering the Km[app] to 83 microM.

  DOI：

  10.1016/0039-128x(83)90040-5

文献信息

• The effects of adrenal and gonadal steroids and K+-canrenoate on the metabolism of aldosterone by rat liver microsomes
  作者：Syed A. Latif、Martin J. McDermott、David J. Morris

  DOI：10.1016/0039-128x(83)90040-5

  日期：1983.9

  The synthesis of polar aldosterone metabolites by rat liver microsomes at physiological concentrations of aldosterone (21.5 nM), was markedly inhibited by progesterone, testosterone, corticosterone, K+-canrenoate and estradiol-17 beta. In contrast, corticosterone and estradiol-17 beta significantly increased the synthesis of reduced aldosterone metabolites by 8- and 15-fold respectively, the majority of which were 5 alpha-reduced products of aldosterone. In experiments at higher substrate (aldosterone) concentrations (20-200 microM) the synthesis of ring A-reduced aldosterone metabolites by liver microsomes followed Michaelis-Menten kinetics with a Km[app] for aldosterone of 160 microM and Vmax[app] of 12.2 nmoles/mg protein/5 min. In these experiments progesterone, testosterone and K+-canrenoate all competitively inhibited the synthesis of reduced metabolites with inhibition constants (Ki [app]) of 70, 85 and 55 microM respectively; however, corticosterone did not. In contrast, estradiol-17 beta increased the rate of synthesis of reduced products by 40%, lowering the Km[app] to 83 microM.
• Kirk, David N.; Rajagopalan, Maruthiandan S., Journal of the Chemical Society. Perkin transactions I, 1987, p. 1343 - 1346
  作者：Kirk, David N.、Rajagopalan, Maruthiandan S.

  DOI：——

  日期：——