(3Z,5Z,7Z,11Z,13Z)-21-{2,4-二羟基-6-[2-({4-羟基-5-[(5-羟基-4-甲氧基-6-甲基四氢-2H-吡喃-2-基)氧基]-4,6-二甲基四氢-2H-吡喃-2-基}氧基)-3-甲氧基丙基]-3,5-二甲基四氢-2H-吡喃-2-基}-10-[(3,4-二羟基-5-甲氧基-6-甲基四氢-2H-吡喃-2-基)氧基]-17,20-二羟基-18-甲氧基-3,5,7,9,13-五甲基氧杂环二十一-3,5,7,11,13-五烯-2-酮 | 476647-30-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 中文名称: (3Z,5Z,7Z,11Z,13Z)-21-{2,4-二羟基-6-[2-({4-羟基-5-[(5-羟基-4-甲氧基-6-甲基四氢-2H-吡喃-2-基)氧基]-4,6-二甲基四氢-2H-吡喃-2-基}氧基)-3-甲氧基丙基]-3,5-二甲基四氢-2H-吡喃-2-基}-10-[(3,4-二羟基-5-甲氧基-6-甲基四氢-2H-吡喃-2-基)氧基]-17,20-二羟基-18-甲氧基-3,5,7,9,13-五甲基氧杂环二十一-3,5,7,11,13-五烯-2-酮
• 中文别名: 异脂蛋白
• 英文名称: isoapoptolidin
• 英文别名: (3E,5E,7E,9R,10R,11E,13E,17S,18S,20S,21R)-21-[(2R,3R,4S,5R,6R)-2,4-dihydroxy-6-[(2R)-2-[(2R,4S,5S,6S)-4-hydroxy-5-[(2S,4R,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4,6-dimethyloxan-2-yl]oxy-3-methoxypropyl]-3,5-dimethyloxan-2-yl]-10-[(2R,3S,4S,5R,6S)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy-17,20-dihydroxy-18-methoxy-3,5,7,9,13-pentamethyl-1-oxacyclohenicosa-3,5,7,11,13-pentaen-2-one
• CAS: 476647-30-0
• 化学式: C₅₈H₉₆O₂₁
• 分子量: 1129.39
• InChiKey: BGIXVQPJBLGABA-PVLPSINKSA-N

物化性质

• 沸点：
  1109.3±65.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：可溶，DMSO：可溶，乙醇：可溶，甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  79
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  290
• 氢给体数：
  8
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  (3Z,5Z,7Z,11Z,13Z)-21-{2,4-二羟基-6-[2-({4-羟基-5-[(5-羟基-4-甲氧基-6-甲基四氢-2H-吡喃-2-基)氧基]-4,6-二甲基四氢-2H-吡喃-2-基}氧基)-3-甲氧基丙基]-3,5-二甲基四氢-2H-吡喃-2-基}-10-[(3,4-二羟基-5-甲氧基-6-甲基四氢-2H-吡喃-2-基)氧基]-17,20-二羟基-18-甲氧基-3,5,7,9,13-五甲基氧杂环二十一-3,5,7,11,13-五烯-2-酮 以 various solvent(s) 为溶剂， 生成 (8E,10E,12R,13R,14E,16E,18E)-12-羟基-13-甲基-20-氧代氧杂环二十-8,10,14,16,18-五烯-2,4,5-三基
  参考文献：
  名称：

  Isoapoptolidin:  Structure and Activity of the Ring-Expanded Isomer of Apoptolidin

  摘要：

  graphicApoptolidin (1) is a novel oncolytic lead that induces apoptosis in transformed cell lines with exceptional selectivity. We report the isolation and characterization of a ring-expanded macrolide isomer of apoptolidin: isoapoptolidin (2). The solution conformation of isoapoptolidin is described. The rate of isomerization was measured under biologically relevant conditions and found to approach equilibrium within the time frame of most cell-based assays. Isoapoptolidin's ability to inhibit mitochondrial F0F1-ATPase is over 10-fold less than that of apoptolidin.

  DOI：

  10.1021/ol0266222
• 作为产物：
  描述：

  (8E,10E,12R,13R,14E,16E,18E)-12-羟基-13-甲基-20-氧代氧杂环二十-8,10,14,16,18-五烯-2,4,5-三基 以 various solvent(s) 为溶剂， 生成 (3Z,5Z,7Z,11Z,13Z)-21-{2,4-二羟基-6-[2-({4-羟基-5-[(5-羟基-4-甲氧基-6-甲基四氢-2H-吡喃-2-基)氧基]-4,6-二甲基四氢-2H-吡喃-2-基}氧基)-3-甲氧基丙基]-3,5-二甲基四氢-2H-吡喃-2-基}-10-[(3,4-二羟基-5-甲氧基-6-甲基四氢-2H-吡喃-2-基)氧基]-17,20-二羟基-18-甲氧基-3,5,7,9,13-五甲基氧杂环二十一-3,5,7,11,13-五烯-2-酮
  参考文献：
  名称：

  Isoapoptolidin:  Structure and Activity of the Ring-Expanded Isomer of Apoptolidin

  摘要：

  graphicApoptolidin (1) is a novel oncolytic lead that induces apoptosis in transformed cell lines with exceptional selectivity. We report the isolation and characterization of a ring-expanded macrolide isomer of apoptolidin: isoapoptolidin (2). The solution conformation of isoapoptolidin is described. The rate of isomerization was measured under biologically relevant conditions and found to approach equilibrium within the time frame of most cell-based assays. Isoapoptolidin's ability to inhibit mitochondrial F0F1-ATPase is over 10-fold less than that of apoptolidin.

  DOI：

  10.1021/ol0266222

文献信息

• Facile Synthetic Access to and Biological Evaluation of the Macrocyclic Core of Apoptolidin
  作者：Paul A. Wender、Orion D. Jankowski、Elie A. Tabet、Haruo Seto

  DOI：10.1021/ol0346335

  日期：2003.6.1

  [GRAPHICS]Oxidative cleavage of the C-20/C-21 bond in apoptolidin (1) provides two fragments of similar complexity, facilitating a divide-and-diversify strategy for the determination of the structural basis for apoptolidin's biological activity, the remarkably selective induction of apoptosis in sensitive cell lines. The ability of compounds derived from this cleavage to inhibit mitochondrial F0F1-ATPase is reported.
• Toward a Stable Apoptolidin Derivative:  Identification of Isoapoptolidin and Selective Deglycosylation of Apoptolidin
  作者：James D. Pennington、Howard J. Williams、Arthur R. Salomon、Gary A. Sulikowski

  DOI：10.1021/ol026829v

  日期：2002.10.1

  graphicIsoapoptolidin was isolated from crude fermentation extracts of the apoptolidin-producing microorganism Nocardiopsis sp. Apoptolidin isomerizes to isoapoptolidin upon treatment with methanolic triethylamine to establish a 1.4:1 equilibrium mixture of isoapoptolidin and apoptolidin. Semisynthesis of a peracetylated and deglycosylated derivative of apoptolidin is also described.
• Isoapoptolidin:  Structure and Activity of the Ring-Expanded Isomer of Apoptolidin
  作者：Paul A. Wender、Aaron V. Gulledge、Orion D. Jankowski、Haruo Seto

  DOI：10.1021/ol0266222

  日期：2002.10.1

  graphicApoptolidin (1) is a novel oncolytic lead that induces apoptosis in transformed cell lines with exceptional selectivity. We report the isolation and characterization of a ring-expanded macrolide isomer of apoptolidin: isoapoptolidin (2). The solution conformation of isoapoptolidin is described. The rate of isomerization was measured under biologically relevant conditions and found to approach equilibrium within the time frame of most cell-based assays. Isoapoptolidin's ability to inhibit mitochondrial F0F1-ATPase is over 10-fold less than that of apoptolidin.