8-HETE | 70968-93-3

• 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: 8-HETE
• 英文别名: 8-hydroxyeicosatetraenoic acid；8-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid；(5Z,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid
• CAS: 70968-93-3
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: NLUNAYAEIJYXRB-HEJOTXCHSA-N

物化性质

• 沸点：
  471.1±45.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

8-HETE是花生四烯酸的已知人类代谢物。

8-HETE is a known human metabolite of arachidonic acid.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  8-HETE 生成 (5Z,9E,11Z,14Z)-8-Trimethylsilanyloxy-icosa-5,9,11,14-tetraenoic acid methyl ester
  参考文献：
  名称：

  5- and 8-HETE production by rat hepatic microsomal cytochrome P-450

  摘要：

  DOI：

  10.1016/s0040-4039(01)80185-4
• 作为产物：
  描述：

  methyl (5Z,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoate 、 氢氧化钾 生成 8-HETE
  参考文献：
  名称：

  KUHN, HARTMUT;WIESNER, RAINER, J. CHROMATOGR. , 520,(1990) C. 391-401

  摘要：

  DOI：

文献信息

• Repurposing Resveratrol and Fluconazole To Modulate Human Cytochrome P450-Mediated Arachidonic Acid Metabolism
  作者：Ahmed A. El-Sherbeni、Ayman O. S. El-Kadi

  DOI：10.1021/acs.molpharmaceut.5b00873

  日期：2016.4.4

  Cytochrome P450 (P450) enzymes metabolize arachidonic acid (AA) to several biologically active epoxyeicosatrienoic acids (EETs) and hydroxyeicosatetraenoic acids (HETEs). Repurposing clinically-approved drugs could provide safe and readily available means to control EETs and HETEs levels in humans. Our aim was to determine how to significantly and selectively modulate P450-AA metabolism in humans by

  细胞色素P450（P450）酶将花生四烯酸（AA）代谢为几种具有生物活性的环氧二十碳三烯酸（EET）和羟基二十碳四烯酸（HETE）。重新使用经过临床批准的药物可以为控制人类中的EET和HETE水平提供安全且容易获得的手段。我们的目标是确定如何通过临床批准的药物显着和选择性地调节人体内的P450-AA代谢。液相色谱-质谱法用于测定人重组P450酶以及人肝和肾微粒体形成的15种AA代谢产物。CYP2C19显示最高的EET形成活性，而CYP1B1和CYP2C8显示最高的中链HETE形成活性。CYP1A1和CYP4分别显示出最高的亚末端和20-HETE形成活性。与研究药物相比，白藜芦醇和氟康唑对肝P450-AA代谢产生了最有选择性和最显着的调节作用。蒙特卡洛模拟显示，每天服用2.5克后，有90％的人口在16-，18-和20-HETE形成中分别减少6-22％，16-39％和16-35％。白藜芦醇，氟康唑50
• PROPHYLACTIC AGENT AND/OR THERAPEUTIC AGENT FOR CATARACT, MEDICINAL COMPOSITION FOR PREVENTING AND/OR TREATING CATARACT, USE OF PPAR ACTIVATOR FOR PRODUCING SAME, AND EYEDROPS
  申请人：University of Fukui

  公开号：EP3733203A1

  公开（公告）日：2020-11-04

  Provided are agents for prevention and therapeutic treatment of cataract that act by a different mechanism from conventional agents, and use of a PPAR activator for production of such agents. An agent for prevention and/or therapeutic treatment of cataract, containing a PPAR activator as an active ingredient, is used.

  本发明提供了预防和治疗白内障的药剂，其作用机理与传统药剂不同，还提供了使用 PPAR 激活剂生产此类药剂的方法。一种用于预防和/或治疗白内障的药剂含有 PPAR 激活剂作为活性成分。
• Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways
  作者：Aldwin Anterola、Cornelia Göbel、Ellen Hornung、George Sellhorn、Ivo Feussner、Howard Grimes

  DOI：10.1016/j.phytochem.2008.11.012

  日期：2009.1

  Mosses have substantial amounts of long chain C20 polyunsaturated fatty acids, such as arachidonic and eicosapentaenoic acid, in addition to the shorter chain C18 alpha-linolenic and linoleic acids, which are typical substrates of lipoxygenases in flowering plants. To identify the fatty acid substrates used by moss lipoxygenases, eight lipoxygenase genes from Physcomitrella patens were heterologously expressed in Escherichia coli, and then analyzed for lipoxygenase activity using linoleic, alpha-linolenic and arachidonic acids as substrates. Among the eight moss lipoxygenases, only seven were found to be enzymatically active in vitro, two of which selectively used arachidonic acid as the substrate, while the other five preferred alpha-linolenic acid. Based on enzyme assays using a Clark-type oxygen electrode, all of the active lipoxygenases had an optimum pH at 7.0, except for one with highest activity at pH 5.0. HPLC analyses indicated that the two arachidonic acid lipoxygenases form (12S)-hydroperoxy eicosatetraenoic acid as the main product, while the other five lipoxygenases produce mainly (13S)-hydroperoxy octadecatrienoic acid from alpha-linolenic acid. These results suggest that mosses may have both C20 and C18 based oxylipin pathways. Published by Elsevier Ltd.
• Oxidation of oxa and thia fatty acids and related compounds catalysed by 5- and 15-lipoxygenase
  作者：Christopher J. Easton、Thomas A. Robertson、Michael J. Pitt、Deborah A. Rathjen、Antonio Ferrante、Alfred Poulos

  DOI：10.1016/s0968-0896(00)00246-7

  日期：2001.2

  The modified fatty acids, (Z,Z,Z)-(octadeca-6,9,12-trienyloxy)acetic acid, (Z,Z,Z)-(octadeca-9,12,15-trienyloxy)acetic acid, (all-Z)-(eicosa-5,8,11,14-tetraenyloxy)acetic acid, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid, 3-[(all-Z)-(eicosa-5,8,11,14-tetraenylthio)]propionic acid, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)succinic acid, N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]glycine and N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]aspartic acid, all react with soybean 15-lipoxygenase. The products were treated with triphenylphosphine to give alcohols, which were isolated using HPLC. Analysis of the alcohols using negative ion tandem electrospray mass spectrometry, and by comparison with compounds obtained by autoxidation of arachidonic acid, shows that each enzyme catalysed oxidation occurs at the omega -6 position of the substrate. In a similar fashion, it has been found that (Z,Z,Z)-(octadeca-6,9,12-trienyloxy)acetic acid, (Z,Z,Z)-(octadeca-9,12,15-trienyloxy)acetic acid, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid and N-[(all-Z)-(eicosa-5,8, 11.14-tetraenylthio)]propionic acid each undergoes regioselective oxidation at the carboxyl end of the polyene moiety on treatment with potato 5-lipoxygenase. Neither (all-Z)-(eicosa-5,8,11,14-tetraenylthio)succinic acid nor N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]aspartic acid reacts in the presence of this enzyme, while N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]glycine affords the C11' oxidation product. The alcohol derived from (Z,Z,Z)-(octadeca-6,9, 12-trienyloxy)acetic acid using the 15-lipoxygenase reacts at the C6' position with the 5-lipoxygenase. (C) 2001 Elsevier Science Ltd. All rights reserved.
• MODIFIED POLYUNSATURATED FATTY ACIDS
  申请人：Peptech Limited

  公开号：EP0869941B1

  公开（公告）日：2001-12-12