14,15-Epoxy-5,8,11-eicosatrienoic acid (BioDeep_00000004023)

Main id: BioDeep_00000628861

 

human metabolite Endogenous blood metabolite


代谢物信息卡片


14,15-Epoxy-5,8,11-eicosatrienoic acid, (2alpha(5Z,8Z,11Z),3alpha)-isomer

化学式: C20H32O3 (320.23513219999995)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 41.79%

分子结构信息

SMILES: C(/C=C\C/C=C\CCCC(=O)O)/C=C\CC1OC1CCCCC
InChI: InChI=1S/C20H32O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,13-10-

描述信息

14,15-epoxy-5,8,11-eicosatrienoic acid is an epoxyeicosatrienoic acid (EET), a metabolite of arachidonic acid. The P450 eicosanoids epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. Four regioisomeric cis-EET are primary products of arachidonic acid metabolism by cytochrome P450 epoxygenases. Upon hydration by soluble epoxide hydrolase (sEH), EET are metabolized to dihydroxyeicosatrienoic acids (DHET). These hydration products are more stable and less biologically active than EETs. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113, 15581597).
14,15-epoxy-5,8,11-eicosatrienoic acid is an epoxyeicosatrienoic acid (EET), a metabolite of arachidonic acid.
D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents

同义名列表

26 个代谢物同义名

14,15-Epoxy-5,8,11-eicosatrienoic acid, (2alpha(5Z,8Z,11Z),3alpha)-isomer; (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoic acid; (±)14(15)-epoxy-5Z,8Z,11Z-eicosatrienoic acid; (5Z,8Z,11Z)-14,15-Epoxyeicosa-5.8.11-trienoic acid; (5Z,8Z,11Z)-14,15-Epoxyicosa-5.8.11-trienoic acid; 14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid-(d8); all-cis-14,15-Epoxyeicosa-5,8,11-trienoic acid; (5Z,8Z,11Z)-14,15-Epoxyeicosa-5.8.11-trienoate; (5Z,8Z,11Z)-14,15-Epoxyicosa-5.8.11-trienoate; all-cis-14,15-Epoxyeicosa-5,8,11-trienoate; 14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid; 14,15-Epoxy-5Z,8Z,11Z-icosatrienoic acid; 14,15-Oxido-5,8,11-eicosatrienoic acid; 14,15-Epoxy-5,8,11-eicosatrienoic acid; 14,15-Epoxy-5Z,8Z,11Z-eicosatrienoate; 14,15-Epoxy-5Z,8Z,11Z-icosatrienoate; 14,15-Epoxy-5,8,11-eicosatrienoate; 14,15-Epoxyeicosatrienoic acid; (±)14,15-EpETrE-(d8); (±)14(15)-EET; (+/-)14,15-EpETrE; 14(15)-EpETrE-EA; 14(15)-EpETrE; 14,15-EpETrE; FA 20:4;O; 14,15-EET



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

47 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(46)

PharmGKB(0)

2 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Jie Zhang, Chuang Yang, Hongmei Qiu, Junxia Yang, Ke Wu, Shumei Ding, Chengyan Jiang, Qingsong Jiang. 14,15-EET involved in the development of diabetic cardiac hypertrophy mediated by PPARs. Prostaglandins & other lipid mediators. 2022 04; 159(?):106620. doi: 10.1016/j.prostaglandins.2022.106620. [PMID: 35091081]
  • Shanthi Nagarajan, Zu Yuan Qian, Parthiban Marimuthu, Nabil J Alkayed, Sanjiv Kaul, Anthony P Barnes. Mapping the Molecular Architecture Required for Lipid-Binding Pockets Using a Subset of Established and Orphan G-Protein Coupled Receptors. Journal of chemical information and modeling. 2021 07; 61(7):3442-3452. doi: 10.1021/acs.jcim.1c00335. [PMID: 34242503]
  • Menglu Fu, Jing Yu, Zhihui Chen, Ying Tang, Ruolan Dong, Yan Yang, Jinlan Luo, Shuiqing Hu, Ling Tu, Xizhen Xu. Epoxyeicosatrienoic acids improve glucose homeostasis by preventing NF-κB-mediated transcription of SGLT2 in renal tubular epithelial cells. Molecular and cellular endocrinology. 2021 03; 523(?):111149. doi: 10.1016/j.mce.2020.111149. [PMID: 33387601]
  • John D Imig, Wojciech K Jankiewicz, Abdul H Khan. Epoxy Fatty Acids: From Salt Regulation to Kidney and Cardiovascular Therapeutics: 2019 Lewis K. Dahl Memorial Lecture. Hypertension (Dallas, Tex. : 1979). 2020 07; 76(1):3-15. doi: 10.1161/hypertensionaha.120.13898. [PMID: 32475311]
  • Ming-Xiao Wang, Li-Jun Wang, Yu Xiao, Dan-Dan Zhang, Xin-Peng Duan, Wen-Hui Wang. Epoxyeicosatrienoic acid metabolites inhibit Kir4.1/Kir5.1 in the distal convoluted tubule. American journal of physiology. Renal physiology. 2020 06; 318(6):F1369-F1376. doi: 10.1152/ajprenal.00018.2020. [PMID: 32308018]
  • Mercè Pallàs, Santiago Vázquez, Coral Sanfeliu, Carles Galdeano, Christian Griñán-Ferré. Soluble Epoxide Hydrolase Inhibition to Face Neuroinflammation in Parkinson's Disease: A New Therapeutic Strategy. Biomolecules. 2020 05; 10(5):. doi: 10.3390/biom10050703. [PMID: 32369955]
  • Yi-Min Kuo, Pei-Chien Hsu, Chia-Chi Hung, Ya-Yu Hu, Yu-Jie Huang, Yu-Ling Gan, Chun-Hua Lin, Feng-Shiun Shie, Wen-Kuei Chang, Lung-Sen Kao, Mei-Yung Tsou, Yi-Hsuan Lee. Soluble Epoxide Hydrolase Inhibition Attenuates Excitotoxicity Involving 14,15-Epoxyeicosatrienoic Acid-Mediated Astrocytic Survival and Plasticity to Preserve Glutamate Homeostasis. Molecular neurobiology. 2019 Dec; 56(12):8451-8474. doi: 10.1007/s12035-019-01669-8. [PMID: 31257558]
  • Uwe Hoff, Gordana Bubalo, Mandy Fechner, Maximilian Blum, Ye Zhu, Andreas Pohlmann, Jan Hentschel, Karen Arakelyan, Erdmann Seeliger, Bert Flemming, Dennis Gürgen, Michael Rothe, Thoralf Niendorf, Vijaya L Manthati, John R Falck, Michael Haase, Wolf-Hagen Schunck, Duska Dragun. A synthetic epoxyeicosatrienoic acid analogue prevents the initiation of ischemic acute kidney injury. Acta physiologica (Oxford, England). 2019 10; 227(2):e13297. doi: 10.1111/apha.13297. [PMID: 31077555]
  • Maxwell Zeigler, Dale Whittington, Nona Sotoodehnia, Rozenn N Lemaitre, Rheem A Totah. A sensitive and improved throughput UPLC-MS/MS quantitation method of total cytochrome P450 mediated arachidonic acid metabolites that can separate regio-isomers and cis/trans-EETs from human plasma. Chemistry and physics of lipids. 2018 11; 216(?):162-170. doi: 10.1016/j.chemphyslip.2018.09.004. [PMID: 30201384]
  • Lu Liu, Nitin Puri, Marco Raffaele, Joseph Schragenheim, Shailendra P Singh, J Alyce Bradbury, Lars Bellner, Luca Vanella, Darryl C Zeldin, Jian Cao, Nader G Abraham. Ablation of soluble epoxide hydrolase reprogram white fat to beige-like fat through an increase in mitochondrial integrity, HO-1-adiponectin in vitro and in vivo. Prostaglandins & other lipid mediators. 2018 09; 138(?):1-8. doi: 10.1016/j.prostaglandins.2018.07.004. [PMID: 30041041]
  • Pinming Liu, Shaoling Zhang, Jingwei Gao, Ying Lin, Guangzi Shi, Wanbing He, Rhian M Touyz, Li Yan, Hui Huang. Downregulated Serum 14, 15-Epoxyeicosatrienoic Acid Is Associated With Abdominal Aortic Calcification in Patients With Primary Aldosteronism. Hypertension (Dallas, Tex. : 1979). 2018 04; 71(4):592-598. doi: 10.1161/hypertensionaha.117.10644. [PMID: 29440332]
  • Jing Luo, Jian-Feng Yao, Xiao-Fei Deng, Xiao-Dan Zheng, Min Jia, Yue-Qin Wang, Yan Huang, Jian-Hua Zhu. 14, 15-EET induces breast cancer cell EMT and cisplatin resistance by up-regulating integrin αvβ3 and activating FAK/PI3K/AKT signaling. Journal of experimental & clinical cancer research : CR. 2018 Feb; 37(1):23. doi: 10.1186/s13046-018-0694-6. [PMID: 29426357]
  • Qi Zhang, Xiang Wang, Guifang Yan, Juan Lei, Yu Zhou, Lei Wu, Ting Wang, Xiao Zhang, Duyun Ye, Yongsheng Li. Anti- Versus Pro-Inflammatory Metabololipidome Upon Cupping Treatment. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2018; 45(4):1377-1389. doi: 10.1159/000487563. [PMID: 29462800]
  • Bing-Qing Deng, Ying Luo, Xin Kang, Chang-Bin Li, Christophe Morisseau, Jun Yang, Kin Sing Stephen Lee, Jian Huang, Da-Yong Hu, Ming-Yu Wu, Ai Peng, Bruce D Hammock, Jun-Yan Liu. Epoxide metabolites of arachidonate and docosahexaenoate function conversely in acute kidney injury involved in GSK3β signaling. Proceedings of the National Academy of Sciences of the United States of America. 2017 11; 114(47):12608-12613. doi: 10.1073/pnas.1705615114. [PMID: 29109264]
  • Theresa Aliwarga, Brianne S Raccor, Rozenn N Lemaitre, Nona Sotoodehnia, Sina A Gharib, Libin Xu, Rheem A Totah. Enzymatic and free radical formation of cis- and trans- epoxyeicosatrienoic acids in vitro and in vivo. Free radical biology & medicine. 2017 11; 112(?):131-140. doi: 10.1016/j.freeradbiomed.2017.07.015. [PMID: 28734877]
  • William B Campbell, John D Imig, James M Schmitz, John R Falck. Orally Active Epoxyeicosatrienoic Acid Analogs. Journal of cardiovascular pharmacology. 2017 Oct; 70(4):211-224. doi: 10.1097/fjc.0000000000000523. [PMID: 28937442]
  • Julia M Santos, Jung-A Park, Aby Joiakim, David A Putt, Robert N Taylor, Hyesook Kim. The role of soluble epoxide hydrolase in preeclampsia. Medical hypotheses. 2017 Oct; 108(?):81-85. doi: 10.1016/j.mehy.2017.07.033. [PMID: 29055406]
  • Xuehong Liu, Zu-Yuan Qian, Fuchun Xie, Wei Fan, Jonathan W Nelson, Xiangshu Xiao, Sanjiv Kaul, Anthony P Barnes, Nabil J Alkayed. Functional screening for G protein-coupled receptor targets of 14,15-epoxyeicosatrienoic acid. Prostaglandins & other lipid mediators. 2017 09; 132(?):31-40. doi: 10.1016/j.prostaglandins.2016.09.002. [PMID: 27649858]
  • Yong Zhou, Tian Liu, Jia-Xi Duan, Ping Li, Guo-Ying Sun, Yong-Ping Liu, Jun Zhang, Liang Dong, Kin Sing Stephen Lee, Bruce D Hammock, Jian-Xin Jiang, Cha-Xiang Guan. Soluble Epoxide Hydrolase Inhibitor Attenuates Lipopolysaccharide-Induced Acute Lung Injury and Improves Survival in Mice. Shock (Augusta, Ga.). 2017 05; 47(5):638-645. doi: 10.1097/shk.0000000000000767. [PMID: 27753791]
  • Amy A Rand, Bogdan Barnych, Christophe Morisseau, Tomas Cajka, Kin Sing Stephen Lee, Dipak Panigrahy, Bruce D Hammock. Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids. Proceedings of the National Academy of Sciences of the United States of America. 2017 04; 114(17):4370-4375. doi: 10.1073/pnas.1616893114. [PMID: 28396419]
  • A Sporková, Z Husková, P Škaroupková, N Rami Reddy, J R Falck, J Sadowski, L Červenka. Vasodilatory responses of renal interlobular arteries to epoxyeicosatrienoic acids analog are not enhanced in Ren-2 transgenic hypertensive rats: evidence against a role of direct vascular effects of epoxyeicosatrienoic acids in progression of experimental heart failure. Physiological research. 2017 03; 66(1):29-39. doi: 10.33549/physiolres.933350. [PMID: 27782740]
  • Becca A Flitter, Kelli L Hvorecny, Emiko Ono, Taylor Eddens, Jun Yang, Daniel H Kwak, Christopher D Bahl, Thomas H Hampton, Christophe Morisseau, Bruce D Hammock, Xinyu Liu, Janet S Lee, Jay K Kolls, Bruce D Levy, Dean R Madden, Jennifer M Bomberger. Pseudomonas aeruginosa sabotages the generation of host proresolving lipid mediators. Proceedings of the National Academy of Sciences of the United States of America. 2017 01; 114(1):136-141. doi: 10.1073/pnas.1610242114. [PMID: 27980032]
  • Ingrid Fleming. The factor in EDHF: Cytochrome P450 derived lipid mediators and vascular signaling. Vascular pharmacology. 2016 11; 86(?):31-40. doi: 10.1016/j.vph.2016.03.001. [PMID: 26975734]
  • Šárka Jíchová, Libor Kopkan, Zuzana Husková, Šárka Doleželová, Jan Neckář, Petr Kujal, Zdenka Vernerová, Herbert J Kramer, Janusz Sadowski, Elzbieta Kompanowska-Jezierska, Rami N Reddy, John R Falck, John D Imig, Luděk Červenka. Epoxyeicosatrienoic acid analog attenuates the development of malignant hypertension, but does not reverse it once established: a study in Cyp1a1-Ren-2 transgenic rats. Journal of hypertension. 2016 10; 34(10):2008-25. doi: 10.1097/hjh.0000000000001029. [PMID: 27428043]
  • Alexandra Sporková, Rami N Reddy, John R Falck, John D Imig, Libor Kopkan, Janusz Sadowski, Luděk Červenka. Interlobular Arteries From 2-Kidney, 1-Clip Goldblatt Hypertensive Rats' Exhibit-Impaired Vasodilator Response to Epoxyeicosatrienoic Acids. The American journal of the medical sciences. 2016 05; 351(5):513-9. doi: 10.1016/j.amjms.2016.02.030. [PMID: 27140711]
  • Dorothee J Funk, Bernd L Sorg, Klaus Kopka, Heinz H Schmeiser. Epoxyeicosatrienoic acids (EETs) form adducts with DNA in vitro. Prostaglandins & other lipid mediators. 2016 03; 123(?):63-7. doi: 10.1016/j.prostaglandins.2016.04.006. [PMID: 27166927]
  • Haitham E El-Sikhry, Nasser Alsaleh, Rambabu Dakarapu, John R Falck, John M Seubert. Novel Roles of Epoxyeicosanoids in Regulating Cardiac Mitochondria. PloS one. 2016; 11(8):e0160380. doi: 10.1371/journal.pone.0160380. [PMID: 27494529]
  • Petra Alánová, Zuzana Husková, Libor Kopkan, Alexandra Sporková, Šárka Jíchová, Jan Neckář, John D Imig, Martina Klevstig, František Kolář, N Rami Reddy, John R Falck, Janusz Sadowski, Akira Nishiyama, Herbert J Kramer, Vojtěch Melenovský, Lenka Červenková, Petr Kujal, Zdenka Vernerová, Luděk Červenka. Orally active epoxyeicosatrienoic acid analog does not exhibit antihypertensive and reno- or cardioprotective actions in two-kidney, one-clip Goldblatt hypertensive rats. Vascular pharmacology. 2015 Oct; 73(?):45-56. doi: 10.1016/j.vph.2015.08.013. [PMID: 26304700]
  • Quan-Fei Zhu, Yan-Hong Hao, Ming-Zhou Liu, Jiang Yue, Jian Ni, Bi-Feng Yuan, Yu-Qi Feng. Analysis of cytochrome P450 metabolites of arachidonic acid by stable isotope probe labeling coupled with ultra high-performance liquid chromatography/mass spectrometry. Journal of chromatography. A. 2015 Sep; 1410(?):154-63. doi: 10.1016/j.chroma.2015.07.100. [PMID: 26253834]
  • Pulin Li, Jamie L Lahvic, Vera Binder, Emily K Pugach, Elizabeth B Riley, Owen J Tamplin, Dipak Panigrahy, Teresa V Bowman, Francesca G Barrett, Garrett C Heffner, Shannon McKinney-Freeman, Thorsten M Schlaeger, George Q Daley, Darryl C Zeldin, Leonard I Zon. Epoxyeicosatrienoic acids enhance embryonic haematopoiesis and adult marrow engraftment. Nature. 2015 Jul; 523(7561):468-71. doi: 10.1038/nature14569. [PMID: 26201599]
  • V Lamounier-Zepter, C Look, W-H Schunck, I Schlottmann, C Woischwill, S R Bornstein, A Xu, I Morano. Interaction of epoxyeicosatrienoic acids and adipocyte fatty acid-binding protein in the modulation of cardiomyocyte contractility. International journal of obesity (2005). 2015 May; 39(5):755-61. doi: 10.1038/ijo.2014.193. [PMID: 25370574]
  • Jiawen Xu, Christophe Morisseau, Jun Yang, Dadala M Mamatha, Bruce D Hammock. Epoxide hydrolase activities and epoxy fatty acids in the mosquito Culex quinquefasciatus. Insect biochemistry and molecular biology. 2015 Apr; 59(?):41-9. doi: 10.1016/j.ibmb.2015.02.004. [PMID: 25686802]
  • John D Imig. Epoxyeicosatrienoic acids, hypertension, and kidney injury. Hypertension (Dallas, Tex. : 1979). 2015 Mar; 65(3):476-82. doi: 10.1161/hypertensionaha.114.03585. [PMID: 25583156]
  • Guangzhi Chen, Renfan Xu, Shasha Zhang, Yinna Wang, Peihua Wang, Matthew L Edin, Darryl C Zeldin, Dao Wen Wang. CYP2J2 overexpression attenuates nonalcoholic fatty liver disease induced by high-fat diet in mice. American journal of physiology. Endocrinology and metabolism. 2015 Jan; 308(2):E97-E110. doi: 10.1152/ajpendo.00366.2014. [PMID: 25389366]
  • Ganggang Yu, Xiangjun Zeng, Hongxia Wang, Qi Hou, Chunting Tan, Qiufen Xu, Haoyan Wang. 14,15-epoxyeicosatrienoic Acid suppresses cigarette smoke extract-induced apoptosis in lung epithelial cells by inhibiting endoplasmic reticulum stress. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2015; 36(2):474-86. doi: 10.1159/000430113. [PMID: 25968975]
  • Lei Yang, Li Ni, Quanlu Duan, Xingxu Wang, Chen Chen, Song Chen, Sandip Chaugai, D C Zeldin, Jia Rong Tang, Dao Wen Wang. CYP epoxygenase 2J2 prevents cardiac fibrosis by suppression of transmission of pro-inflammation from cardiomyocytes to macrophages. Prostaglandins & other lipid mediators. 2015 Jan; 116-117(?):64-75. doi: 10.1016/j.prostaglandins.2015.01.004. [PMID: 25686540]
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