S-(Butylcarbamoyl)-L-cystein | 71084-41-8

• 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: S-(Butylcarbamoyl)-L-cystein
• 英文别名: S-(n-butylcarbamyl)-l-cysteine；(2R)-2-amino-3-(butylcarbamoylsulfanyl)propanoic acid
• CAS: 71084-41-8
• 化学式: C₈H₁₆N₂O₃S
• 分子量: 220.293
• InChiKey: NVGRDJFWLCANRS-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  谷胱甘肽 、 S-(Butylcarbamoyl)-L-cystein 在 phosphate buffer pH 7.4 作用下， 反应 5.33h， 生成 S-(n-butylcarbamoyl)glutathione
  参考文献：
  名称：

  Identification of S-(n-Butylcarbamoyl)glutathione, a Reactive Carbamoylating Agent, as a Biliary Metabolite of Benomyl in the Rat

  摘要：

  Treatment of rats with benomyl [methyl 1-(n-butylcarbamoyl)-2-benzimidazolecarbamate; 100 mg kg(-1) ip] led to the detection of a novel biliary metabolite of this widely used systemic fungicide. By means of on-line liquid chromatography-tandem mass spectrometry, this metabolite was identified as a carbamoylated derivative of glutathione, viz. S-(n-butylcarbamoyl)glutathione (SBuG), whose excretion in bile over 4:5 h accounted for ca. 1% of the dose. In vitro experiments demonstrated that SBuG and the corresponding cysteine adduct exhibited carbamoylating activity toward the thiol groups of free cysteine and glutathione when the elements of n-butyl isocyanate were transferred to the acceptor nucleophiles. SBuG also proved to be highly cytotoxic to isolated rat hepatocytes at a concentration of 1 mM. The results of this study raise the possibility that SBuG may serve as a latent form of n-butyl isocyanate in vivo and thereby mediate some of the adverse effects of benomyl.

  DOI：

  10.1021/jf00048a058
• 作为产物：
  描述：

  L-半胱氨酸盐酸盐无水物 、 异氰酸正丁酯 以 N,N-二甲基甲酰胺 为溶剂， 生成 S-(Butylcarbamoyl)-L-cystein
  参考文献：
  名称：

  S-（炔基和芳基氨基甲酰基）-L-半胱氨酸。

  摘要：

  DOI：

  10.1021/jm50016a009