1-O-β-D-glucopyranosyl-(2S,3R,4E,8E)-2-[(2'R)-hydroxyoctadecanoylamino]-4,8-octadecadiene-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)-2-[(2'R)-hydroxyoctadecanoylamino]-4,8-octadecadiene-1,3-diol
• 英文别名: (2R)-2-hydroxy-N-[(2S,3R,4E,8E)-3-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]octadecanamide
• 化学式: C₄₂H₇₉NO₉
• 分子量: 742.091
• InChiKey: BLFKVICPDXPVLY-IWNRCQDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  52
• 可旋转键数：
  34
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  甲醇 、 1-O-β-D-glucopyranosyl-(2S,3R,4E,8E)-2-[(2'R)-hydroxyoctadecanoylamino]-4,8-octadecadiene-1,3-diol 在 盐酸 作用下， 反应 3.0h， 生成 (2R)-2-hydroxyoctadecanoic acid methyl ester
  参考文献：
  名称：

  来自Monochoria Vaginalis的两种脑苷脂和一种酰基糖基甾醇

  摘要：

  三种新化合物已从Monochria阴道的全植物中分离出来，其特征为：(2S,3R,4E,8E,2'R)-1-O-(β-D-吡喃葡萄糖基)-N-(2'-羟基二十烷酰基) )-4,8-​​鞘二烯、(2S,3R,4E,8E,2'R)-1-O-(β-D-吡喃葡萄糖基)-N-(2'-羟基十八烷酰基)-4,8-​​鞘二烯和7 -oxo-stigmasteryl-3-O-(6'-hexadecanoyl)-β-D-吡喃葡萄糖苷。它们的结构是由光谱和化学证据确定的。

  DOI：

  10.1002/jccs.200300156

文献信息

• Constituents of Crinoidea, 4. Isolation and Structure of Ceramides and Glucocerebrosides from the Feather Star Comanthus japonica
  作者：Masanori Inagaki、Akemi Oyama、Kazuyoshi Arao、Ryuichi Higuchi

  DOI：10.1248/cpb.52.1307

  日期：——

  Five ceramides, JC-1—JC-5, and four glucocerebrosides, JCer-1—JCer-4, have been isolated from their parent ceramide and glucocerebroside molecular species JC and JCer obtained from the less polar lipid fraction of the chloroform/methanol extract of the feather star Comanthus japonica. The structures of these sphingolipids have been determined on the basis of chemical and spectroscopic evidence. Reversed-phase HPLC was effective at isolating these sphingolipids, revealing very close resemblance in their structures. JC-1, JC-3, JC-4, JC-5 and JCer-2, JCer-4 are newly found ceramides and glucocerebrosides, respectively.