(((((1S,2R,3R,4S,5R,6S)-5-(((acetoxymethoxy)((R)-2,3-bis(octanoyloxy)propoxy)phosphoryl)oxy)-6-(butyryloxy)cyclohexane-1,2,3,4-tetrayl)tetrakis(oxy))tetrakis(oxo-l5-phosphanetriyl))octakis(oxy))octakis(methylene) octaacetate | 1257087-63-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: (((((1S,2R,3R,4S,5R,6S)-5-(((acetoxymethoxy)((R)-2,3-bis(octanoyloxy)propoxy)phosphoryl)oxy)-6-(butyryloxy)cyclohexane-1,2,3,4-tetrayl)tetrakis(oxy))tetrakis(oxo-l5-phosphanetriyl))octakis(oxy))octakis(methylene) octaacetate
• CAS: 1257087-63-0
• 化学式: C₅₆H₉₃O₄₄P₅
• 分子量: 1625.2
• InChiKey: SKRYBQLPHQJEPA-SEVVZKDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  105.0
• 可旋转键数：
  58.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  539.4
• 氢给体数：
  0.0
• 氢受体数：
  44.0

反应信息

• 作为产物：
  描述：

  溴甲基乙酸酯 、 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以48%的产率得到(((((1S,2R,3R,4S,5R,6S)-5-(((acetoxymethoxy)((R)-2,3-bis(octanoyloxy)propoxy)phosphoryl)oxy)-6-(butyryloxy)cyclohexane-1,2,3,4-tetrayl)tetrakis(oxy))tetrakis(oxo-l5-phosphanetriyl))octakis(oxy))octakis(methylene) octaacetate
  参考文献：
  名称：

  Membrane-Permeant Phosphoinositide Derivatives as Modulators of Growth Factor Signaling and Neurite Outgrowth

  摘要：

  Phosphoinositides are important signaling molecules that govern a large number of cellular processes such as proliferation, differentiation, membrane remodeling, and survival. Here we introduce a fully synthetic membrane-permeant derivative of a novel, easily accessible, and very potent phosphatidylinositol 3,4,5-trisphosphate [Ptdlns(3,4,5)P-3] mimic: phosphatidylinositol 3,4,5,6-tetrakisphosphate [Ptdlns(3,4,5,6)P-4]. The membrane-permeant PtdIns(3,4,5,6)P-4 derivative activated pathways downstream of phosphatidylinositol 3-kinase (PI3K), including protein kinase 13, p70S6K, mitogen-activated protein kinase, and protein kinase C, more potently than similar membrane-permeant PtdIns(3,4,5)P-3 and PtdIns(3,4)P-2 derivatives in the absence of receptor stimulation. In addition, we demonstrate that treatment of PC12 cells with the membrane-permeant PtdIns(3,4)P-2, PtdIns(3,4,5)P-3, and Ptdlns(3,4,5,6)P-4 derivatives increases the number of neurites per cell in the presence of NGF. This work establishes membrane-permeant phosphoinositides as powerful tools to study PI3K signaling and directly demonstrates that 3-phosphorylated phosphoinositides are instrumental for neurite initiation.

  DOI：

  10.1016/j.chembiol.2009.10.005