(2S,3S,4R,14E)-2-{[(2R)-2-hydroxyoctadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol-1-O-β-D-glucopyranoside

• 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,14E)-2-{[(2R)-2-hydroxyoctadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol-1-O-β-D-glucopyranoside
• 英文别名: nudicaulin C
• 化学式: C₄₉H₉₅NO₁₀
• 分子量: 858.294
• InChiKey: NWJQBYGGUOFEBB-SJZFIZEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.84
• 重原子数：
  60.0
• 可旋转键数：
  42.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  189.17
• 氢给体数：
  8.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S,3S,4R,14E)-2-{[(2R)-2-hydroxyoctadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol-1-O-β-D-glucopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 (2S)-2-hydroxyheptadecanoic acid methyl ester 、 、 甲基 Β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Lipoxygenase inhibitory sphingolipids fromLaunaea nudicaulis

  摘要：

  Four new sphingolipids: nudicaulin A [(2S, 3S, 4R, 14E)-2-{[octadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol; 1], nudicaulin B [(2S, 3S, 4R, 14E)-2-{[(2R)-2-hydroxyoctadecanoyl] amino}tetraeicos-14-ene-1,3,4-triol; 2], nudicaulin C [(2S, 3S, 4R, 14E)-2-{[(2R)-2-hydroxyoctadecanoyl]amino} tetraeicos-14-ene-1,3,4-triol-1-O-beta-D-glucopyranoside; 3], and nudicaulin D [(2S, 3S, 4R)-2-{[(2R, 3S, 12E)-2,3-dihydroxy-eicos- 12-enoyl]amino}octadecane-1,3,4-triol; 4] together with 1-hexatriacontanol, beta-sitosterol, octadecyl 4-hydroxycinnamate, elaidic acid, cholesta-5,22-diene-3,7-diol, oleanolic acid, apigenin, and beta-sitosterol 3-O-beta-D-glucopyranoside were isolated from the methanolic extract of the whole plant of Launaea nudicaulis. Their structures were elucidated using H-1 and C-13 NMR spectra and 2D NMR analyses (HMQC, HMBC, and COSY) in combination with mass spectrometry (EI-MS, HR-EI-MS, FAB-MS, and HR-FAB-MS) experiments and comparison with literature data of related compounds. Compounds 1-4 displayed moderate inhibitory potential against enzyme lipoxygenase in concentration-dependent manner with IC50 value ranges 103-193 mu M.

  DOI：

  10.1080/10286020.2012.680440