(R)-N1-((S)-5-oxohexan-2-yl)-2-tetradecanamidosuccinamide | 1615223-40-9

• 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: (R)-N1-((S)-5-oxohexan-2-yl)-2-tetradecanamidosuccinamide
• 英文别名: (2R)-N-[(2S)-5-oxohexan-2-yl]-2-(tetradecanoylamino)butanediamide
• CAS: 1615223-40-9
• 化学式: C₂₄H₄₅N₃O₄
• 分子量: 439.639
• InChiKey: OESNGSQKCCZCKI-PZJWPPBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-N1-((S)-5-oxohexan-2-yl)-2-tetradecanamidosuccinamide 在 ClbP 作用下， 生成 N-myristoyl-D-asparagine 、 (5S)-5-aminohexan-2-one
  参考文献：
  名称：

  Comparative Metabolomics and Structural Characterizations Illuminate Colibactin Pathway-Dependent Small Molecules

  摘要：

  The gene duster responsible for synthesis of the unknown molecule "colibactin" has been identified in mutualistic and pathogenic Escherichia coli. The pathway endows its producer with a long-term persistence phenotype in the human bowel, a probiotic activity used in the treatment of ulcerative colitis, and a carcinogenic activity under host inflammatory conditions. To date, functional small molecules from this pathway have not been reported. Here we implemented a comparative metabolomics and targeted structural network analyses approach to identify a catalog of small molecules dependent on the colibactin pathway from the meningitis isolate E. coli IHE3034 and the probiotic E. coli Nissle 1917. The structures of 10 pathway-dependent small molecules are proposed based on structural characterizations and network relationships. The network will provide a roadmap for the structural and functional elucidation of a variety of other small molecules encoded by the pathway. From the characterized small molecule set, in vitro bacterial growth inhibitory and mammalian CNS receptor antagonist activities are presented.

  DOI：

  10.1021/ja503450q
• 作为产物：
  描述：

  在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-N1-((S)-5-oxohexan-2-yl)-2-tetradecanamidosuccinamide 、
  参考文献：
  名称：

  Comparative Metabolomics and Structural Characterizations Illuminate Colibactin Pathway-Dependent Small Molecules

  摘要：

  The gene duster responsible for synthesis of the unknown molecule "colibactin" has been identified in mutualistic and pathogenic Escherichia coli. The pathway endows its producer with a long-term persistence phenotype in the human bowel, a probiotic activity used in the treatment of ulcerative colitis, and a carcinogenic activity under host inflammatory conditions. To date, functional small molecules from this pathway have not been reported. Here we implemented a comparative metabolomics and targeted structural network analyses approach to identify a catalog of small molecules dependent on the colibactin pathway from the meningitis isolate E. coli IHE3034 and the probiotic E. coli Nissle 1917. The structures of 10 pathway-dependent small molecules are proposed based on structural characterizations and network relationships. The network will provide a roadmap for the structural and functional elucidation of a variety of other small molecules encoded by the pathway. From the characterized small molecule set, in vitro bacterial growth inhibitory and mammalian CNS receptor antagonist activities are presented.

  DOI：

  10.1021/ja503450q

文献信息

• Comparative Metabolomics and Structural Characterizations Illuminate Colibactin Pathway-Dependent Small Molecules
  作者：Maria I. Vizcaino、Philipp Engel、Eric Trautman、Jason M. Crawford

  DOI：10.1021/ja503450q

  日期：2014.7.2

  The gene duster responsible for synthesis of the unknown molecule "colibactin" has been identified in mutualistic and pathogenic Escherichia coli. The pathway endows its producer with a long-term persistence phenotype in the human bowel, a probiotic activity used in the treatment of ulcerative colitis, and a carcinogenic activity under host inflammatory conditions. To date, functional small molecules from this pathway have not been reported. Here we implemented a comparative metabolomics and targeted structural network analyses approach to identify a catalog of small molecules dependent on the colibactin pathway from the meningitis isolate E. coli IHE3034 and the probiotic E. coli Nissle 1917. The structures of 10 pathway-dependent small molecules are proposed based on structural characterizations and network relationships. The network will provide a roadmap for the structural and functional elucidation of a variety of other small molecules encoded by the pathway. From the characterized small molecule set, in vitro bacterial growth inhibitory and mammalian CNS receptor antagonist activities are presented.