26,26,26,27,27,27-hexafluoro-23S-hydroxycalcitriol

• 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: 26,26,26,27,27,27-hexafluoro-23S-hydroxycalcitriol
• 英文别名: 26,26,26,27,27,27-hexafluoro-1alpha,23(S),25-trihydroxyvitamin D3；(1R,3S,5Z)-5-[(2E)-2-[(7aR)-7a-methyl-1-[(4S)-7,7,7-trifluoro-4,6-dihydroxy-6-(trifluoromethyl)heptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• 化学式: C₂₇H₃₈F₆O₄
• 分子量: 540.587
• InChiKey: SVMOCCGIPIDIDM-QLWBUPQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  氟骨三醇 在 kidney mitochondrial 24-hydroxylase cytochrome P₄₅₀ (CYP₂₄) 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 生成 26,26,26,27,27,27-hexafluoro-23S-hydroxycalcitriol
  参考文献：
  名称：

  Rat CYP24 catalyses 23S-hydroxylation of 26,26,26,27,27,27-hexafluorocalcitriolin vitro

  摘要：

  1. Kidney mitochondrial 24-hydroxylase cytochrome P450 (CYP24) catalyses sequential hydroxylation at both C-24 and C-23 positions of calcidiol and calcitriol. Here, we have investigated the in vitro metabolism of a hexafluorinated derivative of calcitriol, 26,26,26,27,27,27-hexafluorocalcitriol (ST-630), in a reconstituted system by using recombinant Escherichia coli membrane fractions containing rat CYP24.2. When ST-630 was incubated with CYP24 supplemented with bovine adrenodoxin and NADPH-adrenodoxin reductase, a distinct metabolite could be observed. This metabolite was found to be 26,26,26,27,27,27-hexafluoro-23S-hydroxycalcitriol, a biologically active metabolite of ST-630, based on cochromatography on HPLC and mass spectrometric analysis.3. These results show the direct evidence that CYP24 plays an essential role in the metabolism of ST-630 to yield its 23S-hydroxylated metabolite, as observed in cultured cells and experimental animal studies.

  DOI：

  10.1080/004982598239380

文献信息

• Rat CYP24 catalyses 23<i>S</i>-hydroxylation of 26,26,26,27,27,27-hexafluorocalcitriol<i>in vitro</i>
  作者：K. HAYASHI、M. AKIYOSHI-SHIBATA、T. SAKAKI、Y. YABUSAKI*

  DOI：10.1080/004982598239380

  日期：1998.1

  1. Kidney mitochondrial 24-hydroxylase cytochrome P450 (CYP24) catalyses sequential hydroxylation at both C-24 and C-23 positions of calcidiol and calcitriol. Here, we have investigated the in vitro metabolism of a hexafluorinated derivative of calcitriol, 26,26,26,27,27,27-hexafluorocalcitriol (ST-630), in a reconstituted system by using recombinant Escherichia coli membrane fractions containing rat CYP24.2. When ST-630 was incubated with CYP24 supplemented with bovine adrenodoxin and NADPH-adrenodoxin reductase, a distinct metabolite could be observed. This metabolite was found to be 26,26,26,27,27,27-hexafluoro-23S-hydroxycalcitriol, a biologically active metabolite of ST-630, based on cochromatography on HPLC and mass spectrometric analysis.3. These results show the direct evidence that CYP24 plays an essential role in the metabolism of ST-630 to yield its 23S-hydroxylated metabolite, as observed in cultured cells and experimental animal studies.