(2S,3S,4R)-2-{[(2R)-2-hydroxyoctdecanoy]amino}hexaeicosane-1,3,4-triol | 1588950-14-4

• 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: (2S,3S,4R)-2-{[(2R)-2-hydroxyoctdecanoy]amino}hexaeicosane-1,3,4-triol
• 英文别名: plicatin A；(2R)-2-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyhexacosan-2-yl]octadecanamide
• CAS: 1588950-14-4
• 化学式: C₄₄H₈₉NO₅
• 分子量: 712.194
• InChiKey: NDCNELRYVBMFBT-IDAYOUIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.9
• 重原子数：
  50
• 可旋转键数：
  41
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S,3S,4R)-2-{[(2R)-2-hydroxyoctdecanoy]amino}hexaeicosane-1,3,4-triol 在 盐酸 作用下， 以 水 为溶剂， 反应 15.0h， 生成 2-羟基十八烷酸甲酯 、
  参考文献：
  名称：

  New lipoxygenase inhibitory sphingolipids fromChrozophora plicata

  摘要：

  Two new sphingolipids plicatin A [(2S,3S,4R)-2-{[(2R)-2-hydroxyoctdecanoyl]amino}hexaeicosane-1,3,4-triol (1)] and plicatin B [(2S,3S,4R,10E)-2-{[(2R)-2-hydroxyoctdecanoyl]amino}tricont-10-ene-1,3,4-triol (2)], together with 4-hydroxybenzaldehyde, scopoletin, uracil, and dl-threonolactone were isolated from the methanolic extract of the whole plant of Chrozophora plicata. The structures of these compounds were established using 1D (H-1, C-13) and 2D NMR (HMQC, HMBC, and COSY) spectroscopy and mass spectrometry (EI-MS and HR-EI-MS) and in comparison with the reported data in the literature. Compounds 1 and 2 showed inhibitory potential against enzyme lipoxygenase with IC50 values 195.1 and 102.3M, respectively.

  DOI：

  10.1080/10286020.2013.812643

文献信息

• New lipoxygenase inhibitory sphingolipids from<i>Chrozophora plicata</i>
  作者：Naheed Riaz、Asia Tabussum、Muhammad Saleem、Muhammad Ashraf、Romana Nasar、Bushra Jabeen、Abdul Malik、Abdul Jabbar

  DOI：10.1080/10286020.2013.812643

  日期：2013.10

  Two new sphingolipids plicatin A [(2S,3S,4R)-2-[(2R)-2-hydroxyoctdecanoyl]amino}hexaeicosane-1,3,4-triol (1)] and plicatin B [(2S,3S,4R,10E)-2-[(2R)-2-hydroxyoctdecanoyl]amino}tricont-10-ene-1,3,4-triol (2)], together with 4-hydroxybenzaldehyde, scopoletin, uracil, and dl-threonolactone were isolated from the methanolic extract of the whole plant of Chrozophora plicata. The structures of these compounds were established using 1D (H-1, C-13) and 2D NMR (HMQC, HMBC, and COSY) spectroscopy and mass spectrometry (EI-MS and HR-EI-MS) and in comparison with the reported data in the literature. Compounds 1 and 2 showed inhibitory potential against enzyme lipoxygenase with IC50 values 195.1 and 102.3M, respectively.