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 (320.2351)
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。

亚细胞结构定位 关联基因列表
Cytoplasm 12 ANG, CASP3, CYP1A1, CYP2C8, CYP2J2, MAPK14, MAPK8, MTOR, PIK3CA, PPARG, PTGS2, STAT3
Peripheral membrane protein 4 CYP1A1, CYP1B1, MTOR, PTGS2
Endoplasmic reticulum membrane 7 CYP1A1, CYP1B1, CYP2C8, CYP2J2, HMOX1, MTOR, PTGS2
Nucleus 9 ANG, CASP3, HMOX1, MAPK14, MAPK8, MTOR, PPARA, PPARG, STAT3
cytosol 11 ANG, CASP3, EPHX2, HMOX1, MAPK14, MAPK8, MTOR, PIK3CA, PPARG, PRKCQ, STAT3
dendrite 1 MTOR
phagocytic vesicle 1 MTOR
nucleoplasm 8 CASP3, HMOX1, MAPK14, MAPK8, MTOR, PPARA, PPARG, STAT3
RNA polymerase II transcription regulator complex 2 PPARG, STAT3
Cell membrane 1 TNF
Cytoplasmic side 2 HMOX1, MTOR
lamellipodium 1 PIK3CA
Golgi apparatus membrane 1 MTOR
Synapse 1 MAPK8
cell surface 1 TNF
glutamatergic synapse 2 CASP3, MAPK14
Golgi membrane 1 MTOR
growth cone 1 ANG
lysosomal membrane 1 MTOR
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 3 ANG, CASP3, TNF
Lysosome 1 MTOR
plasma membrane 6 CYP2C8, KNG1, PIK3CA, PRKCQ, STAT3, TNF
Membrane 4 CYP1B1, CYP2J2, HMOX1, MTOR
axon 1 MAPK8
caveola 1 PTGS2
extracellular exosome 3 CYP2J2, EPHX2, KNG1
Lysosome membrane 1 MTOR
endoplasmic reticulum 2 HMOX1, PTGS2
extracellular space 5 ANG, CXCL8, HMOX1, KNG1, TNF
perinuclear region of cytoplasm 3 HMOX1, PIK3CA, PPARG
intercalated disc 1 PIK3CA
mitochondrion 3 CYP1A1, CYP1B1, MAPK14
protein-containing complex 1 PTGS2
intracellular membrane-bounded organelle 5 CYP1A1, CYP1B1, CYP2C8, CYP2J2, PPARG
Microsome membrane 5 CYP1A1, CYP1B1, CYP2J2, MTOR, PTGS2
postsynaptic density 1 CASP3
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 2 ANG, CXCL8
extracellular region 5 ANG, CXCL8, KNG1, MAPK14, TNF
Mitochondrion outer membrane 1 MTOR
mitochondrial outer membrane 2 HMOX1, MTOR
transcription regulator complex 1 STAT3
centriolar satellite 1 PRKCQ
external side of plasma membrane 1 TNF
actin cytoskeleton 1 ANG
nucleolus 1 ANG
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 1 TNF
Peroxisome 1 EPHX2
basement membrane 1 ANG
peroxisomal matrix 1 EPHX2
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 1 KNG1
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 PPARG
neuron projection 1 PTGS2
chromatin 3 PPARA, PPARG, STAT3
phagocytic cup 1 TNF
Chromosome 1 ANG
Secreted, extracellular space 1 KNG1
Nucleus, nucleolus 1 ANG
spindle pole 1 MAPK14
blood microparticle 1 KNG1
nuclear envelope 1 MTOR
Endomembrane system 1 MTOR
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 1 ANG
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
endoplasmic reticulum lumen 2 KNG1, PTGS2
platelet alpha granule lumen 1 KNG1
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
endocytic vesicle 1 ANG
immunological synapse 1 PRKCQ
aggresome 1 PRKCQ
Single-pass type IV membrane protein 1 HMOX1
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
Cytoplasmic vesicle, phagosome 1 MTOR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
angiogenin-PRI complex 1 ANG
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
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  • 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]
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  • 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]
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  • 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]
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