(24S)-24-methyl-4β-methyl-5α-cholest-8(14)en-3β-ol | 1562370-63-1

• 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: (24S)-24-methyl-4β-methyl-5α-cholest-8(14)en-3β-ol
• CAS: 1562370-63-1
• 化学式: C₂₉H₅₀O
• 分子量: 414.715
• InChiKey: YDQIBRUWWSGZRH-IFWVRSGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.02
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  dehydroconicasterol 在 platinum oxide on carbon 、 氢气 作用下， 以 正己烷 为溶剂， 反应 0.08h， 以4 mg的产率得到(24S)-24-methyl-4β-methyl-5α-cholest-8(14)en-3β-ol
  参考文献：
  名称：

  Insights on pregnane-X-receptor modulation. Natural and semisynthetic steroids from Theonella marine sponges

  摘要：

  Pregnane-X-receptor (PXR) is a member of nuclear receptors superfamily that activates gene transcription by binding to responsive elements in the promoter of target genes. PXR is a master gene orchestrating the expression/activity of genes involved in the metabolism of endobiotics including bilirubin, bile acids, glucose and lipid. In addition PXR oversights the metabolism of the large majority of xenobiotics including a large amount of prescribing drugs. Thus, developing PXR ligands represents a great opportunity for a therapeutic intervention on human diseases including diabetes, obesity, dyslipidemias and liver disorders. To this end, natural compounds represent an arsenal of new chemical scaffolds useful for the identification of novel PXR ligands. Here, we report a series of 4-methylenesteroid derivatives isolated from Theonella marine sponges as novel PXR modulators. In addition, combining medicinal chemistry, pharmacological experiments and computational studies, we have investigated the effects of different modifications on ring A and on the side chain of 4-methylenesteroid derivatives toward PXR modulation. This study provides the molecular bases of ligand/PXR interaction useful for designing novel PXR modulators. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.005