4,9-dihydroxy-2-nonenoic mercapturic acid

• 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: 4,9-dihydroxy-2-nonenoic mercapturic acid
• 英文别名: 3-(2-Acetamido-2-carboxyethyl)sulfanyl-4,9-dihydroxynonanoic acid；3-(2-acetamido-2-carboxyethyl)sulfanyl-4,9-dihydroxynonanoic acid
• 化学式: C₁₄H₂₅NO₇S
• 分子量: 351.421
• InChiKey: OLDWUSIYSZEWIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  170
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-乙酰-L-半胱氨酸 在 sodium hydroxide 作用下， 以 phosphate buffer 、 水 为溶剂， 反应 26.0h， 生成 4,9-dihydroxy-2-nonenoic mercapturic acid
  参考文献：
  名称：

  Identification of Novel Urinary Metabolites of the Lipid Peroxidation Product 4-Hydroxy-2-nonenal in Rats

  摘要：

  Following iv administration of 4-hydroxy-2-nonenal (HNE) and [4-H-3]HNE to rats, 15 polar urinary metabolites accounting for about 50% of the urinary radioactivity were separated by HPLC, Among them, eight major compounds and tritiated water were quantified. The metabolites were unequivocally characterized using GC/MS and ESI/MS/MS/MS. Most of "HNE polar metabolites" originate from omega-oxidation of 4-hydroxy-2-nonenoic acid(HNA): 9-hydroxy-HNA, its mercapturic acid conjugate, and two diastereoisomers of the corresponding lactone. The oxidation of 9-hydroxy-HNA by alcohol and aldehyde dehydrogenases leads to the excretion of 9-carboxy-HNA and of the corresponding lactone mercapturic acid conjugate. 1,4-Dihydroxy-2-nonene (DHN) originating from the reduction of HNE by alcohol dehydrogenase was to a lesser extent omega-hydroxylated, leading to 9-hydroxy-DHN which was excreted as a mercapturic acid conjugate (two diastereoisomers).

  DOI：

  10.1021/tx980068g

文献信息

• Identification of Novel Urinary Metabolites of the Lipid Peroxidation Product 4-Hydroxy-2-nonenal in Rats
  作者：Jacques Alary、Laurent Debrauwer、Yvette Fernandez、Alain Paris、Jean-Pierre Cravedi、Laurence Dolo、Dinesh Rao、Georges Bories

  DOI：10.1021/tx980068g

  日期：1998.11.1

  Following iv administration of 4-hydroxy-2-nonenal (HNE) and [4-H-3]HNE to rats, 15 polar urinary metabolites accounting for about 50% of the urinary radioactivity were separated by HPLC, Among them, eight major compounds and tritiated water were quantified. The metabolites were unequivocally characterized using GC/MS and ESI/MS/MS/MS. Most of "HNE polar metabolites" originate from omega-oxidation of 4-hydroxy-2-nonenoic acid(HNA): 9-hydroxy-HNA, its mercapturic acid conjugate, and two diastereoisomers of the corresponding lactone. The oxidation of 9-hydroxy-HNA by alcohol and aldehyde dehydrogenases leads to the excretion of 9-carboxy-HNA and of the corresponding lactone mercapturic acid conjugate. 1,4-Dihydroxy-2-nonene (DHN) originating from the reduction of HNE by alcohol dehydrogenase was to a lesser extent omega-hydroxylated, leading to 9-hydroxy-DHN which was excreted as a mercapturic acid conjugate (two diastereoisomers).