11,12-Epoxyeicosatrienoic acid (BioDeep_00000001718)
Main id: BioDeep_00000628861
human metabolite Endogenous blood metabolite
代谢物信息卡片
(5Z,8Z)-10-[(2S,3R)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid
化学式: C20H32O3 (320.23513219999995)
中文名称:
谱图信息:
最多检出来源 Macaca mulatta(otcml) 0.24%
分子结构信息
SMILES: CCCCC/C=C\CC1C(C/C=C\C/C=C\CCCC(=O)O)O1
InChI: InChI=1S/C20H32O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h6,8-10,12-13,18-19H,2-5,7,11,14-17H2,1H3,(H,21,22)/b8-6+,12-9+,13-10+
描述信息
11,12-Epoxyeicosatrienoic acid (CAS: 81276-02-0) is an epoxyeicosatrienoic acid (EET). Induction of CYP2C8 in native coronary artery endothelial cells by beta-naphthoflavone enhances the formation of 11,12-epoxyeicosatrienoic acid, as well as endothelium-derived hyperpolarizing factor-mediated hyperpolarization and relaxation. Transfection of coronary arteries with CYP2C8 antisense oligonucleotides resulted in decreased levels of CYP2C and attenuated the endothelium-derived hyperpolarizing factor-mediated vascular responses. Thus, a CYP-epoxygenase product is an essential component of the endothelium-derived hyperpolarizing factor-mediated relaxation in the porcine coronary artery, and CYP2C8 fulfills the criteria for the coronary endothelium-derived hyperpolarization factor synthase. The role of EETs in the regulation of the cerebral circulation has become more important since it was realized that EETs are produced in another specialized cell type of the brain, the astrocytes. It has become evident that EETs released from astrocytes may mediate cerebral functional hyperemia. Molecular and pharmacological evidence has shown that neurotransmitter release and spillover onto astrocytes can generate EETs. Since these EETs may reach the vasculature via astrocyte foot-processes, they have the same potential as their endothelial counterparts to hyperpolarize and dilate cerebral vessels. P450 enzymes contain heme in their catalytic domain and nitric oxide (NO) appears to bind to these heme moieties and block formation of P450 products, including EETs. Thus, there appears to be crosstalk between P450 enzymes and NO/NO synthase. The role of fatty acid metabolites and cerebral blood flow becomes even more complex in light of data demonstrating that cyclooxygenase products can act as substrates for P450 enzymes (PMID: 17494091, 17434916, 17406062, 17361113, 15581597, 11413051, 10519554). EETs function as autocrine and paracrine mediators. During inflammation, a large amount of arachidonic acid (AA) is released into the cellular milieu and cyclooxygenase enzymes convert this AA to prostaglandins that in turn sensitize pain pathways. However, AA is also converted into natural EETs by cytochrome P450 enzymes. Cytochrome P450 (CYP) epoxygenases convert arachidonic acid into four epoxyeicosatrienoic acid (EET) regioisomers, 5,6-, 8,9-, 11,12-, and 14,15-EET. EETs produce vascular relaxation by activating smooth muscle large-conductance Ca2+-activated K+ channels. In particular, 11,12-epoxy-5Z,8Z,14Z-eicosatrienoic acid has been shown to play a role in the recovery of depleted Ca2+ pools in cultured smooth muscle cells (PMID: 9368016). In addition, EETs have anti-inflammatory effects on blood vessels and in the kidney, promote angiogenesis, and protect ischemic myocardium and the brain. EET levels are typically regulated by soluble epoxide hydrolase (sEH), the major enzyme degrading EETs. Specifically, soluble epoxide hydrolase (sEH) converts EETs into dihydroxyeicosatrienoic acids.
11,12-EpETrE or 11,12-epoxy-5Z,8Z,14Z-eicosatrienoic acid is an epoxyeicosatrienoic acid or an EET derived from arachadonic acid. EETs function as autacrine and paracrine mediators. During inflammation, a large amount of arachidonic acid (AA) is released into the cellular milieu and cyclooxygenase enzymes convert this AA to prostaglandins that in turn sensitize pain pathways. However, AA is also converted to natural epoxyeicosatrienoic acids (EETs) by cytochrome P450 enzymes. Cytochrome P450 (CYP) epoxygenases convert arachidonic acid to four epoxyeicosatrienoic acid (EET) regioisomers, 5,6-, 8,9-, 11,12-, and 14,15-EET. EETs produce vascular relaxation by activating smooth muscle large-conductance Ca2+-activated K+ channels. In particular, 11,12-epoxy-5Z,8Z,14Z-eicosatrienoic acid has been show to play a role in the recovery of depleted Ca2+ pools in cultured smooth muscle cells (PMID: 9368016). In addition, EETs have antiinflammatory effects on blood vessels and in the kidney, promote angiogenesis, and protect ischemic myocardium and brain. EET levels are typically regulated by soluble epoxide hydrolase (sEH), the major enzyme degrading EETs. Specifically, soluble epoxide hydrolase (sEH) converts EETs to dihydroxyeicosatrienoic acids. [HMDB]
D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents
同义名列表
32 个代谢物同义名
(5Z,8Z)-10-[(2S,3R)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid; (5Z,8Z)-10-[(2S,3R)-3-(2Z)-2-Octen-1-yl-2-oxiranyl]-5,8-decadienoic acid; 11,12-Epoxy-5,8,14-eicosatrienoic acid, (2alpha(5Z,8Z),3alpha(Z))-isomer; (5Z,8Z)-10-[3-(2Z)-2-Octen-1-yl-2-oxiranyl]-5,8-decadienoic acid; 10-[3-(2-Octen-1-yl)-2-oxiranyl]-5,8-decadienoic acid; (11S,12R)-Epoxy-(5Z,8Z,14Z)-eicosatrienoic acid; 10-[3-(2-Octenyl)oxiranyl]-5,8-decadienoic acid; (11S,12R)-Epoxy-(5Z,8Z,14Z)-icosatrienoic acid; 11S,12R-epoxy-5Z,8Z,14Z-eicosatrienoic acid; (11S,12R)-Epoxy-(5Z,8Z,14Z)-eicosatrienoate; (11S,12R)-Epoxy-(5Z,8Z,14Z)-icosatrienoate; 11(12)-Epoxy-5Z,8Z,14Z-eicosatrienoic acid; 11S,12R-Epoxy-5Z,8Z,14Z-eicosatrienoate; 11,12-Oxido-5,8,14-eicosatrienoic acid; 11,12-Epoxyeicosa-5,8,14-trienoic acid; 11,12-Epoxy-5,8,14-eicosatrienoic acid; (11S,12R)-Oxidoarachidonic acid; 11,12-Epoxyeicosatrienoic acid; 11,12-Epoxyeicosatrienoate; 11(S),12(R)-EpETrE; cis-11(12)-EpEtrE; (11S,12R)-EpETrE; 11(S),12(R)-EET; 11S,12R-EpETrE; 11(12)-EpETrE; 11,12-EpETrE; 11S,12R-EET; 11(12)-EET; 11,12-EET; (±)11(12)-epoxy-5Z,8Z,14Z-eicosatrienoic acid; 10-(3-oct-2-enyloxiran-2-yl)deca-5,8-dienoic acid; (±)11(12)-EET
数据库引用编号
18 个数据库交叉引用编号
- ChEBI: CHEBI:132276
- KEGG: C14770
- PubChem: 40490664
- PubChem: 1407
- HMDB: HMDB0004673
- Metlin: METLIN3853
- ChEMBL: CHEMBL128117
- foodb: FDB027560
- chemspider: 23208913
- CAS: 123931-40-8
- PMhub: MS000001043
- ChEBI: CHEBI:171868
- PubChem: 17395768
- LipidMAPS: LMFA03080004
- NIKKAJI: J428.163B
- RefMet: 11,12-EpETrE
- PubChem: 5283204
- RefMet: 11S,12R-EpETrE
分类词条
相关代谢途径
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代谢反应
0 个相关的代谢反应过程信息。
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BioCyc(0)
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Plant Reactome(0)
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PharmGKB(0)
1 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。
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文献列表
- Liman Luo, Yan Yang, Menglu Fu, Jinlan Luo, Wenhua Li, Ling Tu, Ruolan Dong. 11,12-EET suppressed LPS induced TF expression and thrombus formation by accelerating mRNA degradation rate via strengthening PI3K-Akt signaling pathway and inhibiting p38-TTP pathway.
Prostaglandins & other lipid mediators.
2023 Apr; 167(?):106740. doi:
10.1016/j.prostaglandins.2023.106740. [PMID: 37119935] - Yiwei Fang, Zheng Zhang, Yun Zhao, Guoqiang Sun, Meilin Peng, Chunyan Liu, Guilin Yi, Kai Zhao, Hui Yang. The value of lipid metabolites 9,10-DOA and 11,12-EET in prenatal diagnosis of fetal heart defects.
Clinica chimica acta; international journal of clinical chemistry.
2023 Apr; 544(?):117330. doi:
10.1016/j.cca.2023.117330. [PMID: 37037297] - Shuiqing Hu, Jinlan Luo, Menglu Fu, Liman Luo, Yueting Cai, Wenhua Li, Yuanyuan Li, Ruolan Dong, Yan Yang, Ling Tu, Xizhen Xu. Soluble epoxide hydrolase deletion attenuated nicotine-induced arterial stiffness via limiting the loss of SIRT1.
American journal of physiology. Heart and circulatory physiology.
2021 08; 321(2):H353-H368. doi:
10.1152/ajpheart.00979.2020. [PMID: 34142887] - John D Imig, Md Abdul Hye Khan, Anna Burkhan, Guan Chen, Adeniyi Michael Adebesin, John R Falck. Kidney-Targeted Epoxyeicosatrienoic Acid Analog, EET-F01, Reduces Inflammation, Oxidative Stress, and Cisplatin-Induced Nephrotoxicity.
International journal of molecular sciences.
2021 Mar; 22(6):. doi:
10.3390/ijms22062793. [PMID: 33801911] - 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] - Cuiping Zhang, Zuojian Hu, Ke Wang, Lujie Yang, Yue Li, Hartmut Schlüter, Pengyuan Yang, Jiaxu Hong, Hongxiu Yu. Lipidomic profiling of virus infection identifies mediators that resolve herpes simplex virus-induced corneal inflammatory lesions.
The Analyst.
2020 Jun; 145(11):3967-3976. doi:
10.1039/d0an00263a. [PMID: 32319474] - 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] - Marco Rahm, Juliane Merl-Pham, Jerzy Adamski, Stefanie M Hauck. Time-resolved phosphoproteomic analysis elucidates hepatic 11,12-Epoxyeicosatrienoic acid signaling pathways.
Prostaglandins & other lipid mediators.
2020 02; 146(?):106387. doi:
10.1016/j.prostaglandins.2019.106387. [PMID: 31669255] - Marco Raffaele, Lars Bellner, Shailendra P Singh, Gaia Favero, Rita Rezzani, Luigi Fabrizio Rodella, John R Falck, Nader G Abraham, Luca Vanella. Epoxyeicosatrienoic intervention improves NAFLD in leptin receptor deficient mice by an increase in PGC1α-HO-1-PGC1α-mitochondrial signaling.
Experimental cell research.
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Prostaglandins & other lipid mediators.
2018 09; 138(?):1-8. doi:
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Journal of cellular and molecular medicine.
2018 03; 22(3):1489-1500. doi:
10.1111/jcmm.13412. [PMID: 29265525] - Xiaoyan Huang, Yuguang Wang, Yi Wang, Liang Yang, Jia Wang, Yue Gao. Ophiopogonin D Reduces Myocardial Ischemia-Reperfusion Injury via Upregulating CYP2J3/EETs in Rats.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology.
2018; 49(4):1646-1658. doi:
10.1159/000493500. [PMID: 30227401] - 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] - 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:
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Proceedings of the National Academy of Sciences of the United States of America.
2017 04; 114(17):4370-4375. doi:
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Vascular pharmacology.
2016 11; 86(?):31-40. doi:
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Aging cell.
2016 10; 15(5):940-52. doi:
10.1111/acel.12507. [PMID: 27416746] - Marco Di Pascoli, Francesca Zampieri, Alberto Verardo, Paola Pesce, Cristian Turato, Paolo Angeli, David Sacerdoti, Massimo Bolognesi. Inhibition of epoxyeicosatrienoic acid production in rats with cirrhosis has beneficial effects on portal hypertension by reducing splanchnic vasodilation.
Hepatology (Baltimore, Md.).
2016 09; 64(3):923-30. doi:
10.1002/hep.28686. [PMID: 27312119] - 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] - 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] - 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] - Yan Ma, Peng Zhang, Jie Li, Jun Lu, Jianjun Ge, Zhiwei Zhao, Xin Ma, Song Wan, Xiaoqiang Yao, Bing Shen. Epoxyeicosatrienoic acids act through TRPV4-TRPC1-KCa1.1 complex to induce smooth muscle membrane hyperpolarization and relaxation in human internal mammary arteries.
Biochimica et biophysica acta.
2015 Mar; 1852(3):552-9. doi:
10.1016/j.bbadis.2014.12.010. [PMID: 25511389] - Wenshu Chen, Shijiang Yang, Wei Ping, Xiangning Fu, Qinzi Xu, Jianing Wang. CYP2J2 and EETs protect against lung ischemia/reperfusion injury via anti-inflammatory effects in vivo and in vitro.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology.
2015; 35(5):2043-54. doi:
10.1159/000374011. [PMID: 25870948] - Wen-Hui Wang, Chengbiao Zhang, Dao-Hong Lin, Lijun Wang, Joan P Graves, Darryl C Zeldin, Jorge H Capdevila. Cyp2c44 epoxygenase in the collecting duct is essential for the high K+ intake-induced antihypertensive effect.
American journal of physiology. Renal physiology.
2014 Aug; 307(4):F453-60. doi:
10.1152/ajprenal.00123.2014. [PMID: 24966089] - Yindi Ding, Timo Frömel, Rüdiger Popp, John R Falck, Wolf-Hagen Schunck, Ingrid Fleming. The biological actions of 11,12-epoxyeicosatrienoic acid in endothelial cells are specific to the R/S-enantiomer and require the G(s) protein.
The Journal of pharmacology and experimental therapeutics.
2014 Jul; 350(1):14-21. doi:
10.1124/jpet.114.214254. [PMID: 24763066] - Yingmei Liu, Xiaodan Lu, Sinh Nguyen, Jean L Olson, Heather K Webb, Deanna L Kroetz. Epoxyeicosatrienoic acids prevent cisplatin-induced renal apoptosis through a p38 mitogen-activated protein kinase-regulated mitochondrial pathway.
Molecular pharmacology.
2013 Dec; 84(6):925-34. doi:
10.1124/mol.113.088302. [PMID: 24092818] - Md Abdul Hye Khan, Jing Liu, Ganesh Kumar, Stephen X Skapek, John R Falck, John D Imig. Novel orally active epoxyeicosatrienoic acid (EET) analogs attenuate cisplatin nephrotoxicity.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2013 Aug; 27(8):2946-56. doi:
10.1096/fj.12-218040. [PMID: 23603837] - Annemarieke E Loot, Isabelle Moneke, Benjamin Keserü, Matthias Oelze, Tetyana Syzonenko, Andreas Daiber, Ingrid Fleming. 11,12-EET stimulates the association of BK channel α and β(1) subunits in mitochondria to induce pulmonary vasoconstriction.
PloS one.
2012; 7(9):e46065. doi:
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Prostaglandins & other lipid mediators.
2011 Nov; 96(1-4):63-71. doi:
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Prostaglandins & other lipid mediators.
2011 Nov; 96(1-4):76-83. doi:
10.1016/j.prostaglandins.2011.08.001. [PMID: 21854866] - David Sacerdoti, Houli Jiang, Silvia Gaiani, John C McGiff, Angelo Gatta, Massimo Bolognesi. 11,12-EET increases porto-sinusoidal resistance and may play a role in endothelial dysfunction of portal hypertension.
Prostaglandins & other lipid mediators.
2011 Nov; 96(1-4):72-5. doi:
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Prostaglandins & other lipid mediators.
2011 Nov; 96(1-4):54-62. doi:
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Cell biology and toxicology.
2011 Oct; 27(5):321-32. doi:
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American journal of physiology. Renal physiology.
2011 Sep; 301(3):F672-81. doi:
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American journal of physiology. Heart and circulatory physiology.
2011 Jun; 300(6):H1990-6. doi:
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Prostaglandins & other lipid mediators.
2011 Feb; 94(1-2):25-33. doi:
10.1016/j.prostaglandins.2010.12.001. [PMID: 21167292] - Peng Sun, Dao-Hong Lin, Peng Yue, Houli Jiang, Katherine H Gotlinger, Michal L Schwartzman, John R Falck, Mohan Goli, Wen-Hui Wang. High potassium intake enhances the inhibitory effect of 11,12-EET on ENaC.
Journal of the American Society of Nephrology : JASN.
2010 Oct; 21(10):1667-77. doi:
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The Journal of pharmacology and experimental therapeutics.
2009 Dec; 331(3):906-16. doi:
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Journal of the American Society of Nephrology : JASN.
2009 Mar; 20(3):513-23. doi:
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American journal of physiology. Renal physiology.
2008 Dec; 295(6):F1696-704. doi:
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American journal of physiology. Renal physiology.
2008 Jun; 294(6):F1441-7. doi:
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Hypertension (Dallas, Tex. : 1979).
2008 May; 51(5):1379-85. doi:
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Microcirculation (New York, N.Y. : 1994).
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