(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetoxy-3,4-dihydroxy-3,6,9-trimethyl-8-{[(Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-3a,7-diyl dioctanoate | 1432520-76-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetoxy-3,4-dihydroxy-3,6,9-trimethyl-8-{[(Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-3a,7-diyl dioctanoate
• 英文别名: [(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-3,4-dihydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-3a-octanoyloxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] octanoate
• CAS: 1432520-76-7
• 化学式: C₃₈H₅₈O₁₂
• 分子量: 706.871
• InChiKey: PEDQYKCHEKUXKN-WTAVWCDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  50
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  172
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  丁酸酐 、 (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetoxy-3,4-dihydroxy-3,6,9-trimethyl-8-{[(Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-3a,7-diyl dioctanoate 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以95%的产率得到[(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3-hydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-3a-octanoyloxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] octanoate
  参考文献：
  名称：

  Water-Mediated Interactions Influence the Binding of Thapsigargin to Sarco/Endoplasmic Reticulum Calcium Adenosinetriphosphatase

  摘要：

  A crystal structure suggests four water molecules are present in the binding cavity of thapsigargin in sarco/endoplasmic reticulum calcium ATPase (SERCA). Computational chemistry indicates that three of these water molecules mediate an extensive hydrogen-bonding network between thapsigargin and the backbone of SERCA. The orientation of the thapsigargin molecule in SERCA is crucially dependent on these interactions. The hypothesis has been verified by measuring the affinity of newly synthesized model compounds, which are prevented from participating in such water-mediated interactions as hydrogen-bond donors.

  DOI：

  10.1021/jm4001083
• 作为产物：
  描述：

  毒胡萝卜素 在 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 水 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 92.0h， 生成 (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetoxy-3,4-dihydroxy-3,6,9-trimethyl-8-{[(Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-3a,7-diyl dioctanoate
  参考文献：
  名称：

  Water-Mediated Interactions Influence the Binding of Thapsigargin to Sarco/Endoplasmic Reticulum Calcium Adenosinetriphosphatase

  摘要：

  A crystal structure suggests four water molecules are present in the binding cavity of thapsigargin in sarco/endoplasmic reticulum calcium ATPase (SERCA). Computational chemistry indicates that three of these water molecules mediate an extensive hydrogen-bonding network between thapsigargin and the backbone of SERCA. The orientation of the thapsigargin molecule in SERCA is crucially dependent on these interactions. The hypothesis has been verified by measuring the affinity of newly synthesized model compounds, which are prevented from participating in such water-mediated interactions as hydrogen-bond donors.

  DOI：

  10.1021/jm4001083