3-Carboxy-3-hydroxy-2-(4-nonyl-3-oxo-tetrahydro-furan-2-ylmethyl)-pentanedioic 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: 3-Carboxy-3-hydroxy-2-(4-nonyl-3-oxo-tetrahydro-furan-2-ylmethyl)-pentanedioic acid
• 英文别名: 2-Hydroxy-4-(4-nonyl-3-oxooxolan-2-yl)butane-1,2,3-tricarboxylic acid
• 化学式: C₂₀H₃₂O₉
• 分子量: 416.469
• InChiKey: LOSWKHSWZJXLMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  158
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Trachyspic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 3-Carboxy-3-hydroxy-2-(4-nonyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-pentanedioic acid 、 2-Carboxymethyl-8-nonyl-9-oxo-1,6-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid 、 3-Carboxy-3-hydroxy-2-(4-nonyl-3-oxo-tetrahydro-furan-2-ylmethyl)-pentanedioic acid
  参考文献：
  名称：

  Trachyspic Acid, a New Metabolite Produced by Talaromyces trachyspermus, that Inhibits Tumor Cell Heparanase: Taxonomy of the Producing Strain, Fermentation, Isolation, Structural Elucidation, and Biological Activity.

  摘要：

  Trachyspic acid, a new metabolite that inhibited heparanase, was isolated from the culture broth of Talaromyces trachyspermus SANK 12191. Its structure was deduced from NMR spectral analyses and chemical reactions as a tricarboxylic acid derivative containing a spiroketal. The IC50 value of trachyspic acid against heparanase was 36 μM.

  DOI：

  10.7164/antibiotics.48.357