4α-methyl-5α-cholesta-8(14),24-dien-3β-ol

• 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: 4α-methyl-5α-cholesta-8(14),24-dien-3β-ol
• 英文别名: 4a-Methyl-5a-cholest-8(14),24-dien-3b-ol；(3S,4S,5S,9R,10S,13R,17R)-4,10,13-trimethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,4,5,6,7,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 化学式: C₂₈H₄₆O
• 分子量: 398.673
• InChiKey: VUCKOSSMMLWAEH-GQZGFCDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  植物甾醇 在 25-azacoprostane hydrochloride 作用下， 以 水 为溶剂， 生成 4-甲基胆甾-7-烯-3-醇 、 (3β,4α,5α)-4-methylcholestan-3-ol 、 4α-methyl-5α-cholesta-7,24-dien-3β-ol 、 4α-methyl-5α-cholesta-8(14),24-dien-3β-ol
  参考文献：
  名称：

  Novel nuclear methylation of sterols by the nematode caenorhabditis elegans

  摘要：

  Caenorhabditis elegans possesses a unique sterol methylation pathway not reported to occur in any other organism and also removes the C-24 ethyl group of sitosterol (a plant sterol). This nematode produced substantial quantities of 4 alpha-methyl-5 alpha-cholest-8(14)-en-3 beta-ol and smaller amounts of lophenol from dietary cholesterol, desmosterol or sitosterol. When C. elegans was propagated in media containing sitosterol plus 25-azacoprostane hydrochloride (25-aza-5 beta-cholestane hydrochloride), an inhibitor of delta 24-sterol reductase in insects, its 4 alpha-methylsterol fraction largely consisted of equal amounts of 4 alpha-methyl-5 alpha-cholesta-7,24-dien-3 beta-ol and 4 alpha-methyl-5 alpha-cholesta-8(14),24-dien-3 beta-ol. Thus 25-azacoprostane hydrochloride inhibited both a delta 24-sterol reductase and a delta 7-sterol isomerase in C. elegans.

  DOI：

  10.1016/0039-128x(83)90042-9

文献信息

• Novel nuclear methylation of sterols by the nematode caenorhabditis elegans
  作者：David J. Chitwood、William R. Lusby、Ruben Lozano、Malcolm J. Thompson、James A. Svoboda

  DOI：10.1016/0039-128x(83)90042-9

  日期：1983.9

  Caenorhabditis elegans possesses a unique sterol methylation pathway not reported to occur in any other organism and also removes the C-24 ethyl group of sitosterol (a plant sterol). This nematode produced substantial quantities of 4 alpha-methyl-5 alpha-cholest-8(14)-en-3 beta-ol and smaller amounts of lophenol from dietary cholesterol, desmosterol or sitosterol. When C. elegans was propagated in media containing sitosterol plus 25-azacoprostane hydrochloride (25-aza-5 beta-cholestane hydrochloride), an inhibitor of delta 24-sterol reductase in insects, its 4 alpha-methylsterol fraction largely consisted of equal amounts of 4 alpha-methyl-5 alpha-cholesta-7,24-dien-3 beta-ol and 4 alpha-methyl-5 alpha-cholesta-8(14),24-dien-3 beta-ol. Thus 25-azacoprostane hydrochloride inhibited both a delta 24-sterol reductase and a delta 7-sterol isomerase in C. elegans.