(±)-14,15-epoxy-5Z,8Z,11Z,17Z-eicosatetraenoic acid | 851378-94-4

• 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: (±)-14,15-epoxy-5Z,8Z,11Z,17Z-eicosatetraenoic acid
• 英文别名: 14,15-epoxieicosatetraenoic acid；14,15-epoxyeicosatetraenoic acid；14,15-EETeTr；14,15-EpETE；14,15-EEQ；(+/-)-14(15)-epoxy-5Z,8Z,11Z,17Z-eicosatetraenoic acid；14(15)-EpETE；(5Z,8Z,11Z)-13-[3-[(Z)-pent-2-enyl]oxiran-2-yl]trideca-5,8,11-trienoic acid
• CAS: 851378-94-4
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: RGZIXZYRGZWDMI-QXBXTPPVSA-N

物化性质

• 沸点：
  464.6±33.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  全顺式二十碳五烯酸 在 human recombinant cytochrome P₄₅₀ 2C₈ 作用下， 以41%的产率得到17,18-Epoxyeicosatetraenoic acid
  参考文献：
  名称：

  Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450

  摘要：

  Cytochromes P450 (CYPs) metabolize polyunsaturated long-chain fatty acids (PUFA-LC) to several classes of oxygenated metabolites. Through use of human recombinant CYPs, we recently showed that CYP1A1, -2C19, -2D6, -2E1, and -3A4 are mainly hydroxylases, whereas CYP1A2, -2C8, -2C9, and -2J2 are mainly epoxygenases of arachidonic acid (AA), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA), respectively. It is worth noting that the last double bond of these PUFAs, i.e., omega 6 in AA or omega 3 in EPA and DHA, respectively, was preferentially epoxidized. In this study, we have characterized the stereoselectivity of this epoxidation reaction by comparison with the PUFA-LC epoxide stereoisomers obtained from the enantioselective bacterial CYP102A1 F87V. The stereoselectivity of the epoxidation of the last olefin of AA (omega 6), EPA (omega 3), or DHA (omega 3) differed between the CYP isoforms but was similar for EPA and DHA. These data give additional insight into the PUFA-LC epoxide enantiomers generated by the hepatic CYPs.-Lucas, D., S. Goulitquer, J. Marienhagen, M. Fer, Y. Dreano, U. Schwaneberg, Y. Amet, and L. Corcos. Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450. J. Lipid Res. 2010. 51: 1125-1133.

  DOI：

  10.1194/jlr.m003061

文献信息

• Diagnosing prostate cancer relapse
  申请人：IMG Institut für medizinische Genomforschung Planungsgesellschaft M.B.H.

  公开号：EP2354794A1

  公开（公告）日：2011-08-10

  The invention discloses the use of at least one substance selected from the group consisting of Phosphatidylcholine with diacyl residue sum C24:0 (PC aa C24:0); Phosphatidylcholine with diacyl residue sum C40:3 (PC ae C40:3); Phosphatidylcholine with diacyl residue sum C40:4 (PC ae C40:4); Lysophosphatidylcholine with acyl residue sum C26:0 (lysoPC a C26:0); Lysophosphatidylcholine with acyl residue sum C6:0 (lysoPC a C6:0); 13(S)-hydroxy-9Z,11E-octadecadienoic acid (13S-HODE); 12(S)-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid (12S-HETE); 15(S)-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid (15S-HETE); Leukotriene B4 (LTB4); Prostaglandin E2 (PGE2); Prostaglandin D2 (PGD2); 7α-Hydroxycholesterol (7aOHC); 7-Ketocholesterol (7KC); 5β,6β-Epoxycholesterol (5b,6b,EPC); 5α,6α-Epoxycholesterol (5a,6a,EPC); and 4β-Hydroxycholesterol (4BOHC); for prognosing relapse of a prostate cancer (PCa) in a sample of a body fluid or a tissue sample of a PCa patient.

  本发明公开了至少一种选自以下组别的物质的用途：二酰基残基总和为 C24:0 的磷脂酰胆碱（PC aa C24:0）；二酰基残基总和为 C40：3（PC ae C40:3）；二酰基残基总和为 C40:4（PC ae C40:4）的磷脂酰胆碱；酰基残基总和为 C26:0（lysoPC a C26:0）的溶血磷脂酰胆碱；酰基残基总和为 C6:0（lysoPC a C6：0）；13(S)-羟基-9Z,11E-十八碳二烯酸（13S-HODE）；12(S)-羟基-5Z,8Z,10E,14Z-二十碳四烯酸（12S-HETE）；15（S）-羟基-5Z,8Z,11Z,13E-二十碳四烯酸（15S-HETE）；白三烯 B4（LTB4）；前列腺素 E2（PGE2）；前列腺素 D2（PGD2）；7α-羟基胆固醇（7aOHC）；7-酮胆固醇（7KC）；5β,6β-环氧胆固醇（5b,6b,EPC）；5α,6α-环氧胆固醇（5a,6a,EPC）；以及 4β-羟基胆固醇（4BOHC）；用于预测 PCa 患者体液样本或组织样本中前列腺癌（PCa）复发的情况。
• Methods of inhibiting pain
  申请人：The Regents of the University of California

  公开号：US10813894B2

  公开（公告）日：2020-10-27

  Provided are methods and compositions for preventing, reducing, mitigating and treating pain, particularly neuropathic pain by the combined administration of an agent that increases EETs and an agent that reduces/inhibits endoplasmic reticulum (ER) stress.

  本文提供了通过联合施用增加 EETs 的制剂和减少/抑制内质网（ER）应激的制剂来预防、减少、减轻和治疗疼痛，特别是神经性疼痛的方法和组合物。
• NEW BIOMARKERS FOR ASSESSING KIDNEY DISEASES
  申请人：BIOCRATES Life Sciences AG

  公开号：EP2438441B1

  公开（公告）日：2014-05-21
• STABLE ANALOGS OF CYP450 LIPID METABOLITES AND INHIBITORS OF SOLUBLE EPOXIDE HYDROLASE
  申请人：Massachusetts Eye & Ear Infirmary

  公开号：EP3377056B1

  公开（公告）日：2020-09-23
• Use of inhibitors of soluble epoxide hydrolase to synergize activity of COX and 5-LOX inhibitors
  申请人：Hammock D. Bruce

  公开号：US20060178347A1

  公开（公告）日：2006-08-10

  The invention relates to methods, compositions, and uses of those compositions for making medicaments, for potentiating the beneficial effects of inhibitors of COX-1, COX-2, and 5-LOX, and reducing adverse effects, by also administering inhibitors of soluble epoxide hydrolase (“sEH”), with or without also administering one or more cis-epoxyeicosantrienoic acids. The invention further relates to the use of inhibitors of sEH as analgesics and to methods and compositions of epoxides of eicosapentaenoic acid and docosahexaenoic acid, optionally with an inhibitor of sEH, to reduce pain or inflammation or both.