1-O-(β-D-Glucopyranosyl)-(2S,3R,4E,8E,10E)-2-<(2R)-2-hydroxytetracosanoylamino>-9-methyl-4,8,10-octadecatriene-1,3-diol

• 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: 1-O-(β-D-Glucopyranosyl)-(2S,3R,4E,8E,10E)-2-<(2R)-2-hydroxytetracosanoylamino>-9-methyl-4,8,10-octadecatriene-1,3-diol
• 英文别名: Ophidiacerebroside E；Agelasphin-10；(2R)-2-hydroxy-N-[(2S,3R,4E,8E,10E)-3-hydroxy-9-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8,10-trien-2-yl]tetracosanamide
• 化学式: C₄₉H₉₁NO₉
• 分子量: 838.263
• InChiKey: XOUUYTODOBFFFN-QSDQOXQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  59
• 可旋转键数：
  39
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-O-(β-D-Glucopyranosyl)-(2S,3R,4E,8E,10E)-2-<(2R)-2-hydroxytetracosanoylamino>-9-methyl-4,8,10-octadecatriene-1,3-diol 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 以37.4 mg的产率得到methyl (2R)-2-hydroxytetracosanoate
  参考文献：
  名称：

  Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge Agelas mauritianus

  摘要：

  New glycosphingolipids, named agelasphins (1-8), have been isolated by antitumor and immunostimulatory bioassay-guided purification from an extract of a marine sponge, Agelas mauritianus. Strongly active agents in agelasphins had characteristic ol-galactosylceramide structures, the isolation of which from natural products has not previously been reported. The absolute configurations of agelasphins were elucidated by the total synthesis.

  DOI：

  10.1016/s0040-4020(01)86991-x

文献信息

• Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge Agelas mauritianus
  作者：Takenori Natori、Masahiro Morita、Kohji Akimoto、Yasuhiko Koezuka

  DOI：10.1016/s0040-4020(01)86991-x

  日期：1994.2

  New glycosphingolipids, named agelasphins (1-8), have been isolated by antitumor and immunostimulatory bioassay-guided purification from an extract of a marine sponge, Agelas mauritianus. Strongly active agents in agelasphins had characteristic ol-galactosylceramide structures, the isolation of which from natural products has not previously been reported. The absolute configurations of agelasphins were elucidated by the total synthesis.