(3E)-nonenoyl-CoA(4-)

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3E)-nonenoyl-CoA(4-)
• 英文别名: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[[[[(3R)-3-hydroxy-2,2-dimethyl-4-[[3-[2-[(E)-non-3-enoyl]sulfanylethylamino]-3-oxopropyl]amino]-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]oxolan-3-yl] phosphate
• 化学式: C30H46N7O17P3S-4
• 分子量: 901.7
• InChiKey: VCVDAYMNOMYZHZ-KZKUDURGSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  58
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  400
• 氢给体数：
  5
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  (3E)-nonenoyl-CoA(4-) 生成 trans-2-nonenoyl-CoA(4-)
  参考文献：
  名称：

  Identification and characterization of Eci3, a murine kidney‐specific Δ³, Δ²‐enoyl‐CoA isomerase

  摘要：

  Oxidation of unsaturated fatty acids requires the action of auxiliary enzymes, such as (3),(2)-enoyl-CoA isomerases. Here we describe a detailed biochemical, molecular, histological, and evolutionary characterization of Eci3, the fourth member of the mammalian enoyl-CoA isomerase family. Eci3 specifically evolved in rodents after gene duplication of Eci2. Eci3 is with 79% identity homologous to Eci2 and contains a peroxisomal targeting signal type 1. Subcellular fractionation of mouse kidney and immunofluorescence studies revealed a specific peroxisomal localization for Eci3. Expression studies showed that mouse Eci3 is almost exclusively expressed in kidney. By using immunohistochemistry, we found that Eci3 is not only expressed in cells of the proximal tubule, but also in a subset of cells in the tubulointerstitium and the glomerulus. In vitro, Eci3 catalyzed the isomerization of trans-3-nonenoyl-CoA to trans-2-nonenoyl-CoA equally efficient as Eci2, suggesting a role in oxidation of unsaturated fatty acids. However, in contrast to Eci2, in silico gene coexpression and enrichment analysis for Eci3 in kidney did not yield carboxylic acid metabolism, but diverse biological functions, such as ion transport (P=7.1E-3) and tissue morphogenesis (P=1.0E-3). Thus, Eci3 picked up a novel and unexpected role in kidney function during rodent evolution.van Weeghel, M., Ofman, R., Argmann, C. A., Ruiter, J. P. N., Claessen, N., Oussoren, S. V., Wanders, R. J. A., Aten, J., Houten, S. M. Identification and characterization of Eci3, a murine kidney-specific (3),(2)-enoyl-CoA isomerase.

  DOI：

  10.1096/fj.13-240416