[(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3a-hexanoyloxy-3-hydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] octanoate | 1432520-78-9

• 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-acetyloxy-4-butanoyloxy-3a-hexanoyloxy-3-hydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] octanoate
• CAS: 1432520-78-9
• 化学式: C₄₀H₆₀O₁₃
• 分子量: 748.909
• InChiKey: ZDAQFASDEQBRLM-YNYWTGOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  53
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  Octanoic acid (2aS,5aS,7S,7aR,8S,9S,10bS,10cR)-7-acetoxy-10c-hydroxy-2a,4,4,7,10-pentamethyl-9-((Z)-2-methyl-but-2-enoyloxy)-2-oxo-2,2a,5a,6,7,7a,8,9,10b,10c-decahydro-1,3,5-trioxa-benzo[cd]cyclopenta[h]azulen-8-yl ester 在 盐酸 、 4-二甲氨基吡啶 、 水 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 64.33h， 生成 [(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3a-hexanoyloxy-3-hydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-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

文献信息

• Water-Mediated Interactions Influence the Binding of Thapsigargin to Sarco/Endoplasmic Reticulum Calcium Adenosinetriphosphatase
  作者：Eleonora S. Paulsen、Jesper Villadsen、Eleonora Tenori、Huizhen Liu、Ditte F. Bonde、Mette A. Lie、Maike Bublitz、Claus Olesen、Henriette E. Autzen、Ingrid Dach、Pankaj Sehgal、Poul Nissen、Jesper V. Møller、Birgit Schiøtt、S. Brøgger Christensen

  DOI：10.1021/jm4001083

  日期：2013.5.9

  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.