(2S)-1-O-5,8,11,14,17-eicosapentaenoyl-2-O-6,9,12-hexadecatrienoyl-3-O-[β-D-galactopyranosyl]glycerol | 1038401-98-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2S)-1-O-5,8,11,14,17-eicosapentaenoyl-2-O-6,9,12-hexadecatrienoyl-3-O-[β-D-galactopyranosyl]glycerol
• 英文别名: [(2S)-2-[(6Z,9Z,12Z)-hexadeca-6,9,12-trienoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• CAS: 1038401-98-7
• 化学式: C₄₅H₇₀O₁₀
• 分子量: 771.045
• InChiKey: SHAALCCXWADAJS-GSJBGMJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  55
• 可旋转键数：
  33
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S)-1-O-5,8,11,14,17-eicosapentaenoyl-2-O-6,9,12-hexadecatrienoyl-3-O-[β-D-galactopyranosyl]glycerol 在 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 全顺式二十碳五烯酸 、
  参考文献：
  名称：

  Apoptosis-Inducing Galactolipids from a Cultured Marine Diatom, Phaeodactylum tricornutum

  摘要：

  Two monogalactosyl diacylglycerols, 1 and 2, were isolated from the marine diatom Phaeodactylum tricornutum, using the patented ApopScreen cell-based screen for apoptosis-inducing, potential anticancer compounds. The molecular structures of the galactolipids were determined using a combination of NMR, mass spectrometry, and chemical degradation. The bioactivities were confirmed using a specific apoptosis induction assay based on genetically engineered mammalian cell lines with differential, defined capacities for apoptosis. The galactolipids induce apoptosis in micromolar concentrations. This is the first report of apoptosis induction by galactolipids.

  DOI：

  10.1021/np800124k

文献信息

• Apoptosis-Inducing Galactolipids from a Cultured Marine Diatom, <i>Phaeodactylum tricornutum</i>
  作者：Eric H. Andrianasolo、Liti Haramaty、Assaf Vardi、Eileen White、Richard Lutz、Paul Falkowski

  DOI：10.1021/np800124k

  日期：2008.7.1

  Two monogalactosyl diacylglycerols, 1 and 2, were isolated from the marine diatom Phaeodactylum tricornutum, using the patented ApopScreen cell-based screen for apoptosis-inducing, potential anticancer compounds. The molecular structures of the galactolipids were determined using a combination of NMR, mass spectrometry, and chemical degradation. The bioactivities were confirmed using a specific apoptosis induction assay based on genetically engineered mammalian cell lines with differential, defined capacities for apoptosis. The galactolipids induce apoptosis in micromolar concentrations. This is the first report of apoptosis induction by galactolipids.