(5R,6R)-5-ethyl-6-((2R,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethyl-6-((2S*,3S*)-3-methyloxiran-2-yl)hexyl)-5,6-dihydro-2H-pyran-2-one | 205933-20-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5R,6R)-5-ethyl-6-((2R,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethyl-6-((2S*,3S*)-3-methyloxiran-2-yl)hexyl)-5,6-dihydro-2H-pyran-2-one
• 英文别名: epoxypironetin；(2R,3R)-3-ethyl-2-[(2R,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethyl-6-(3-methyloxiran-2-yl)hexyl]-2,3-dihydropyran-6-one
• CAS: 205933-20-6
• 化学式: C₁₉H₃₂O₅
• 分子量: 340.46
• InChiKey: AQQJWCANVMFTFP-WGTZLYHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-乙基-5,6-二氢-6-[(2R,3S,4R,5S,7E)-2-羟基-4-甲氧基-3,5-二甲基-7-壬烯-1-基]-,(5R,6R)-2H-吡喃-2-酮 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到(5R,6R)-5-ethyl-6-((2R,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethyl-6-((2S*,3S*)-3-methyloxiran-2-yl)hexyl)-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (−)–Pironetin

  摘要：

  Pironetin, the only crystallographically confirmed natural product to target a-tubulin, displays potent cytotoxic activity against sensitive and resistant A2780 ovarian cancer cell lines but is only marginally active in vivo. We now report that pironetin has a short half-life (<7 min) in human liver microsomes, suggesting that its limited in vivo efficacy is due to rapid metabolism. Further, we describe the discovery of epoxypironetin as pironetin's major metabolite in human liver microsomes.

  DOI：

  10.1021/acs.jmedchem.8b01774

文献信息

• Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (−)–Pironetin
  作者：Sara K. Coulup、David S. Huang、Henry L. Wong、Gunda I. Georg

  DOI：10.1021/acs.jmedchem.8b01774

  日期：2019.2.14

  Pironetin, the only crystallographically confirmed natural product to target a-tubulin, displays potent cytotoxic activity against sensitive and resistant A2780 ovarian cancer cell lines but is only marginally active in vivo. We now report that pironetin has a short half-life (<7 min) in human liver microsomes, suggesting that its limited in vivo efficacy is due to rapid metabolism. Further, we describe the discovery of epoxypironetin as pironetin's major metabolite in human liver microsomes.