5Z,7E,9E,14Z-eicosatetraenoyl-N-ethanolamide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5Z,7E,9E,14Z-eicosatetraenoyl-N-ethanolamide
• 英文别名: (5Z,7E,9E,14Z)-N-(2-hydroxyethyl)icosa-5,7,9,14-tetraenamide
• 化学式: C₂₂H₃₇NO₂
• 分子量: 347.541
• InChiKey: GIDPARAKVXCKDP-YSYHEPPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  大麻素 生成 5Z,7E,9E,14Z-eicosatetraenoyl-N-ethanolamide
  参考文献：
  名称：

  Synthesis and cannabinoid receptor binding activity of conjugated triene anandamide, a novel eicosanoid

  摘要：

  A polyenoic fatty-acid isomerase (PFI) from a led marine alga was used to convert anandamide (5Z,8Z,11Z,14Z-eicosatetraenoyl-N-ethanolamide) to the 5Z,7E,9E,14Z-eicosatetraenoyl-N-ethanolamide isomer. This novel eicosanoid, termed conjugated triene anandamide (CTA), was assessed for its ability to bind to the cannabinoid receptor in rat brain membrane preparations. CTA is a high affinity cannabimimetic substance whose novel structure provides new insight into structure-activity relationships of cannabinoid receptor ligands. These experiments illustrate the utility of enzymes isolated from marine organisms in the development of pharmacological probes.

  DOI：

  10.1007/bf01922423

文献信息

• Synthesis and cannabinoid receptor binding activity of conjugated triene anandamide, a novel eicosanoid
  作者：M. L. Wise、K. Soderstrom、T. F. Murray、W. H. Gerwick

  DOI：10.1007/bf01922423

  日期：1996.1

  A polyenoic fatty-acid isomerase (PFI) from a led marine alga was used to convert anandamide (5Z,8Z,11Z,14Z-eicosatetraenoyl-N-ethanolamide) to the 5Z,7E,9E,14Z-eicosatetraenoyl-N-ethanolamide isomer. This novel eicosanoid, termed conjugated triene anandamide (CTA), was assessed for its ability to bind to the cannabinoid receptor in rat brain membrane preparations. CTA is a high affinity cannabimimetic substance whose novel structure provides new insight into structure-activity relationships of cannabinoid receptor ligands. These experiments illustrate the utility of enzymes isolated from marine organisms in the development of pharmacological probes.