Hexacosanoic acid {(1S,2S,3R)-2,3-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxymethyl]-heptadecyl}-amide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: Hexacosanoic acid {(1S,2S,3R)-2,3-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxymethyl]-heptadecyl}-amide
• 英文别名: N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
• 化学式: C₅₆H₁₀₉NO₁₄
• 分子量: 1020.48
• InChiKey: RASDCPXYYYIVJN-JAJDWJTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  71
• 可旋转键数：
  47
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  248
• 氢给体数：
  10
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  在 钯 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 Hexacosanoic acid {(1S,2S,3R)-2,3-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxymethyl]-heptadecyl}-amide
  参考文献：
  名称：

  Immunostimulatory activities of monoglycosylated α-d-pyranosylceramides

  摘要：

  We compared the immunostimulatory effects of chemically synthesized alpha-galactosylceramides (alpha-GalCers), alpha-glucosylceramides (alpha-GluCers), 6 "-monoglycosylated alpha-GalCer and 6 "- or 4 "-monoglycosylated alpha-GluCer and made the following observations: (1) the length of the fatty acid side chain in the ceramide portions greatly affects the immunostimulatory effects of alpha-GalCers and alpha-GluCers; (2) the configuration of the 4 "-hydroxyl group of the inner pyranose moiety plays an important role in the immunostimulatory effects of monoglycosylated alpha-D-pyranosylceramides; (3) the free 4 "-hydroxyl group of the inner pyranose of monoglycosylated alpha-D-pyranosylceramides plays a more important role in their immunostimulatory effects than the free 6 "-hydroxyl group. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00169-7

文献信息

• Immunostimulatory activities of monoglycosylated α-d-pyranosylceramides
  作者：Akira Uchimura、Toshiyuki Shimizu、Masahiro Morita、Hitomi Ueno、Kazuhiro Motoki、Hideaki Fukushima、Takenori Natori、Yasuhiko Koezuka

  DOI：10.1016/s0968-0896(97)00169-7

  日期：1997.12

  We compared the immunostimulatory effects of chemically synthesized alpha-galactosylceramides (alpha-GalCers), alpha-glucosylceramides (alpha-GluCers), 6 "-monoglycosylated alpha-GalCer and 6 "- or 4 "-monoglycosylated alpha-GluCer and made the following observations: (1) the length of the fatty acid side chain in the ceramide portions greatly affects the immunostimulatory effects of alpha-GalCers and alpha-GluCers; (2) the configuration of the 4 "-hydroxyl group of the inner pyranose moiety plays an important role in the immunostimulatory effects of monoglycosylated alpha-D-pyranosylceramides; (3) the free 4 "-hydroxyl group of the inner pyranose of monoglycosylated alpha-D-pyranosylceramides plays a more important role in their immunostimulatory effects than the free 6 "-hydroxyl group. (C) 1997 Elsevier Science Ltd.