14R,15S-EpETrE (BioDeep_00000019035)
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 (320.2351)
中文名称: 14(S),15(R)-环氧-(5Z,8Z,11Z)-二十碳三烯酸
谱图信息:
最多检出来源 Homo sapiens(lipidomics) 61.9%
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)
描述信息
14R,15S-EpETrE is the dominant extracellular metabolite of epoxygenase products of arachidonic acid released from human luteinised granulosa cells. Epoxyeicosatrienoic acids (EpETrEs) have been reported recently having vasodilatory effects and a role of P-450-dependent arachidonic acid monooxygenase metabolites is suggested in vasoregulation. The physiological role of this compound has not been totally established, although in other tissues EpETrEs are mainly involved in hormone production and in the vascular and renal systems. Some studies have implicated epoxygenase metabolites of arachidonic acid in the control of steroidogenesis in luteinised granulosa cells. (PMID: 12749593, 12361727, 1650001) [HMDB]
14R,15S-EpETrE is the dominant extracellular metabolite of epoxygenase products of arachidonic acid released from human luteinised granulosa cells. Epoxyeicosatrienoic acids (EpETrEs) have been reported recently having vasodilatory effects and a role of P-450-dependent arachidonic acid monooxygenase metabolites is suggested in vasoregulation. The physiological role of this compound has not been totally established, although in other tissues EpETrEs are mainly involved in hormone production and in the vascular and renal systems. Some studies have implicated epoxygenase metabolites of arachidonic acid in the control of steroidogenesis in luteinised granulosa cells. (PMID: 12749593, 12361727, 1650001).
D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents
同义名列表
22 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-[(2R,3S)-3-pentyloxiran-2-yl]trideca-5,8,11-trienoic acid; (5Z,8Z,11Z)-14,15-Epoxyeicosa-5.8.11-trienoic acid; 14(S),15(R)-Epoxy-(5Z,8Z,11Z)-eicosatrienoic acid; (5Z,8Z,11Z)-14,15-Epoxyicosa-5.8.11-trienoic acid; (14R,15S)-Epoxy-(5Z,8Z,11Z)-eicosatrienoic acid; (14R,15S)-Epoxy-(5Z,8Z,11Z)-icosatrienoic acid; 14(S),15(R)-Epoxy-(5Z,8Z,11Z)-eicosatrienoate; 14R,15S-epoxy-5Z,8Z,11Z-eicosatrienoic acid; (14R,15S)-Epoxy-(5Z,8Z,11Z)-eicosatrienoate; (14R,15S)-Epoxy-(5Z,8Z,11Z)-icosatrienoate; 14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid; 14R,15S-Epoxy-5Z,8Z,11Z-eicosatrienoate; 14,15-Oxido-5,8,11-eicosatrienoic acid; 14,15-Epoxy-5,8,11-eicosatrienoic acid; 14,15-Epoxyeicosatrienoic acid; (+/-)14,15-EpETrE; (14R,15S)-EpETrE; 14(S),15(R)-EET; 14R,15S-EpETrE; FA 20:4;O; 14,15-EET
数据库引用编号
22 个数据库交叉引用编号
- ChEBI: CHEBI:171866
- ChEBI: CHEBI:132275
- ChEBI: CHEBI:34157
- ChEBI: CHEBI:88823
- KEGG: C14771
- PubChem: 5283205
- PubChem: 5283201
- PubChem: 1431
- HMDB: HMDB0002283
- ChEMBL: CHEMBL564452
- ChEMBL: CHEMBL269319
- LipidMAPS: LMFA03080005
- foodb: FDB022946
- chemspider: 4446322
- CAS: 105304-92-5
- CAS: 197508-62-6
- CAS: 98103-48-1
- CAS: 81276-03-1
- PMhub: MS000014723
- PubChem: 17395769
- NIKKAJI: J185.460G
- RefMet: 14R,15S-EpETrE
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
2 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
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:
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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:
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Journal of experimental & clinical cancer research : CR.
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Free radical biology & medicine.
2017 11; 112(?):131-140. doi:
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Journal of cardiovascular pharmacology.
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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.
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Vascular pharmacology.
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Journal of chromatography. A.
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Nature.
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Insect biochemistry and molecular biology.
2015 Apr; 59(?):41-9. doi:
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Hypertension (Dallas, Tex. : 1979).
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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.
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Prostaglandins & other lipid mediators.
2015 Jan; 116-117(?):64-75. doi:
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Prostaglandins & other lipid mediators.
2014 Aug; 112(?):1-8. doi:
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Lipids in health and disease.
2013 Oct; 12(?):151. doi:
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Prostaglandins & other lipid mediators.
2013 Jul; 104-105(?):25-31. doi:
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Prostaglandins & other lipid mediators.
2013 Jul; 104-105(?):8-17. doi:
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Prostaglandins & other lipid mediators.
2013 Jul; 104-105(?):42-8. doi:
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Prostaglandins & other lipid mediators.
2013 Jul; 104-105(?):67-73. doi:
10.1016/j.prostaglandins.2012.09.003. [PMID: 23000418] - Garrett J Gross, Anna Hsu, Adam W Pfeiffer, Kasem Nithipatikom. Roles of endothelial nitric oxide synthase (eNOS) and mitochondrial permeability transition pore (MPTP) in epoxyeicosatrienoic acid (EET)-induced cardioprotection against infarction in intact rat hearts.
Journal of molecular and cellular cardiology.
2013 Jun; 59(?):20-9. doi:
10.1016/j.yjmcc.2013.02.003. [PMID: 23419451] - Nataliya Pidkovka, Reena Rao, Shaojun Mei, Yan Gong, Raymond C Harris, Wen-Hui Wang, Jorge H Capdevila. Epoxyeicosatrienoic acids (EETs) regulate epithelial sodium channel activity by extracellular signal-regulated kinase 1/2 (ERK1/2)-mediated phosphorylation.
The Journal of biological chemistry.
2013 Feb; 288(7):5223-31. doi:
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PloS one.
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Prostaglandins & other lipid mediators.
2012 Dec; 99(3-4):68-78. doi:
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