(3S,14R)-ochratoxin A | 1208353-99-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: (3S,14R)-ochratoxin A
• 英文别名: N-(((3S)-5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl)-D-phenylalanine；3S14R-Ochratoxin A；(2R)-2-[[(3S)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl]amino]-3-phenylpropanoic acid
• CAS: 1208353-99-4
• 化学式: C₂₀H₁₈ClNO₆
• 分子量: 403.819
• InChiKey: RWQKHEORZBHNRI-ZUZCIYMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Ochratoxin A methyl ester 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 14.0h， 生成 (3S,14R)-ochratoxin A 、 ochratoxin A
  参考文献：
  名称：

  Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers

  摘要：

  The mycotoxin ochratoxin A is a potent inhibitor of the protein biosynthesis and known to be cytotoxic in nanomolar concentrations. In order to investigate the relationship between stereochemistry and cytotoxicity of this compound, all four ochratoxin A stereoisomers have been synthesized. Using the liver cell line Hep G2, the compounds were tested for cytotoxic and apoptotic potential. It could be shown, that the L-configuration of the phenylalanine moiety of the molecule is mostly responsible for the high cytotoxicity of ochratoxin A while the stereocenter at the dihydroisocoumarine structure is of less importance. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.050