20-Hydroxyarachlidonic acid (BioDeep_00000174776)

   

human metabolite blood metabolite


代谢物信息卡片


20-hydroxyicosa-5,8,11,14-tetraenoic acid

化学式: C20H32O3 (320.2351)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: OCCCCCC=CCC=CCC=CCC=CCCCC(O)=O
InChI: InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)



数据库引用编号

4 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

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)

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。

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


文献列表

  • Guangrui Lai, Jingjing Wu, Xiaoliang Liu, Yanyan Zhao. 20-HETE induces hyperglycemia through the cAMP/PKA-PhK-GP pathway. Molecular endocrinology (Baltimore, Md.). 2012 Nov; 26(11):1907-16. doi: 10.1210/me.2012-1139. [PMID: 22918876]
  • Xiaoliang Liu, Jingjing Wu, Hong Liu, Guangrui Lai, Yanyan Zhao. Disturbed ratio of renal 20-HETE/EETs is involved in androgen-induced hypertension in cytochrome P450 4F2 transgenic mice. Gene. 2012 Sep; 505(2):352-9. doi: 10.1016/j.gene.2012.02.029. [PMID: 22387726]
  • Emmanuelle Plée-Gautier, Joseph Antoun, Sophie Goulitquer, Catherine Le Jossic-Corcos, Brigitte Simon, Yolande Amet, Jean-Pierre Salaün, Laurent Corcos. Statins increase cytochrome P450 4F3-mediated eicosanoids production in human liver cells: a PXR dependent mechanism. Biochemical pharmacology. 2012 Aug; 84(4):571-9. doi: 10.1016/j.bcp.2012.05.012. [PMID: 22634049]
  • Cristiano Fava, Marco Ricci, Olle Melander, Pietro Minuz. Hypertension, cardiovascular risk and polymorphisms in genes controlling the cytochrome P450 pathway of arachidonic acid: A sex-specific relation?. Prostaglandins & other lipid mediators. 2012 Aug; 98(3-4):75-85. doi: 10.1016/j.prostaglandins.2011.11.007. [PMID: 22173545]
  • Li Chen, Rachel Ackerman, Austin M Guo. 20-HETE in neovascularization. Prostaglandins & other lipid mediators. 2012 Aug; 98(3-4):63-8. doi: 10.1016/j.prostaglandins.2011.12.005. [PMID: 22227460]
  • Haixia Zhao, Ying Li, Yuzhong Wang, Jing Zhang, Xiaoming Ouyang, Renxiu Peng, Jing Yang. Antitumor and immunostimulatory activity of a polysaccharide-protein complex from Scolopendra subspinipes mutilans L. Koch in tumor-bearing mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Aug; 50(8):2648-55. doi: 10.1016/j.fct.2012.05.018. [PMID: 22613217]
  • Maria M Federik Fernandez, Daniel Gonzalez, Jan M Williams, Richard J Roman, Susana Nowicki. Inhibitors of 20-hydroxyeicosatetraenoic acid (20-HETE) formation attenuate the natriuretic effect of dopamine. European journal of pharmacology. 2012 Jul; 686(1-3):97-103. doi: 10.1016/j.ejphar.2012.04.039. [PMID: 22575524]
  • Jun Yang, Jason P Eiserich, Carroll E Cross, Brian M Morrissey, Bruce D Hammock. Metabolomic profiling of regulatory lipid mediators in sputum from adult cystic fibrosis patients. Free radical biology & medicine. 2012 Jul; 53(1):160-71. doi: 10.1016/j.freeradbiomed.2012.05.001. [PMID: 22580336]
  • Anna Alexanian, Bradley Miller, Richard J Roman, Andrey Sorokin. 20-HETE-producing enzymes are up-regulated in human cancers. Cancer genomics & proteomics. 2012 Jul; 9(4):163-9. doi: . [PMID: 22798501]
  • Katherine N Theken, Robert N Schuck, Matthew L Edin, Bryant Tran, Kyle Ellis, Almasa Bass, Fred B Lih, Kenneth B Tomer, Samuel M Poloyac, Michael C Wu, Alan L Hinderliter, Darryl C Zeldin, George A Stouffer, Craig R Lee. Evaluation of cytochrome P450-derived eicosanoids in humans with stable atherosclerotic cardiovascular disease. Atherosclerosis. 2012 Jun; 222(2):530-6. doi: 10.1016/j.atherosclerosis.2012.03.022. [PMID: 22503544]
  • Svetlana Nikolaeva, Sylvain Pradervand, Gabriel Centeno, Vlasta Zavadova, Natsuko Tokonami, Marc Maillard, Olivier Bonny, Dmitri Firsov. The circadian clock modulates renal sodium handling. Journal of the American Society of Nephrology : JASN. 2012 Jun; 23(6):1019-26. doi: 10.1681/asn.2011080842. [PMID: 22440902]
  • Jan M Williams, Fan Fan, Sydney Murphy, Carlos Schreck, Jozef Lazar, Howard J Jacob, Richard J Roman. Role of 20-HETE in the antihypertensive effect of transfer of chromosome 5 from Brown Norway to Dahl salt-sensitive rats. American journal of physiology. Regulatory, integrative and comparative physiology. 2012 May; 302(10):R1209-18. doi: 10.1152/ajpregu.00604.2011. [PMID: 22442195]
  • Ting Tian, Jin Li, Meng-Ying Wang, Xian-Fei Xie, Qi-Xiong Li. Protective effect of 20-hydroxyeicosatetraenoic acid (20-HETE) on adriamycin-induced toxicity of human renal tubular epithelial cell (HK-2). European journal of pharmacology. 2012 May; 683(1-3):246-51. doi: 10.1016/j.ejphar.2012.03.001. [PMID: 22421401]
  • A Paliege, T Roeschel, H Neymeyer, S Seidel, T Kahl, A L Daigeler, K Mutig, R Mrowka, N R Ferreri, B S Wilson, N Himmerkus, M Bleich, S Bachmann. Group VIA phospholipase A2 is a target for vasopressin signaling in the thick ascending limb. American journal of physiology. Renal physiology. 2012 Apr; 302(7):F865-74. doi: 10.1152/ajprenal.00222.2011. [PMID: 22218592]
  • Mohamad Navab, Srinivasa T Reddy, G M Anantharamaiah, Greg Hough, Georgette M Buga, Jan Danciger, Alan M Fogelman. D-4F-mediated reduction in metabolites of arachidonic and linoleic acids in the small intestine is associated with decreased inflammation in low-density lipoprotein receptor-null mice. Journal of lipid research. 2012 Mar; 53(3):437-445. doi: 10.1194/jlr.m023523. [PMID: 22167743]
  • Katherine N Theken, Yangmei Deng, Robert N Schuck, Akinyemi Oni-Orisan, Tricia M Miller, M Alison Kannon, Samuel M Poloyac, Craig R Lee. Enalapril reverses high-fat diet-induced alterations in cytochrome P450-mediated eicosanoid metabolism. American journal of physiology. Endocrinology and metabolism. 2012 Mar; 302(5):E500-9. doi: 10.1152/ajpendo.00370.2011. [PMID: 22185841]
  • Kevin R Regner, Richard J Roman. Role of medullary blood flow in the pathogenesis of renal ischemia-reperfusion injury. Current opinion in nephrology and hypertension. 2012 Jan; 21(1):33-8. doi: 10.1097/mnh.0b013e32834d085a. [PMID: 22080855]
  • Bahar Tunctan, Belma Korkmaz, Ayse Nihal Sari, Meltem Kacan, Demet Unsal, Mehmet Sami Serin, C Kemal Buharalioglu, Seyhan Sahan-Firat, Wolf-Hagen Schunck, John R Falck, Kafait U Malik. A novel treatment strategy for sepsis and septic shock based on the interactions between prostanoids, nitric oxide, and 20-hydroxyeicosatetraenoic acid. Anti-inflammatory & anti-allergy agents in medicinal chemistry. 2012; 11(2):121-50. doi: 10.2174/187152312803305759. [PMID: 23013331]
  • Yasunori Sato, Xiang Shan Ren, Yasuni Nakanuma. Caroli's Disease: Current Knowledge of Its Biliary Pathogenesis Obtained from an Orthologous Rat Model. International journal of hepatology. 2012; 2012(?):107945. doi: 10.1155/2012/107945. [PMID: 22007315]
  • Guangrui Lai, Xiaoliang Liu, Jingjing Wu, Hong Liu, Yanyan Zhao. Evaluation of CMV and KAP promoters for driving the expression of human CYP4F2 in transgenic mice. International journal of molecular medicine. 2012 Jan; 29(1):107-12. doi: 10.3892/ijmm.2011.787. [PMID: 21887457]
  • Fady T Botros, Leszek Dobrowolski, L Gabriel Navar. Renal heme oxygenase-1 induction with hemin augments renal hemodynamics, renal autoregulation, and excretory function. International journal of hypertension. 2012; 2012(?):189512. doi: 10.1155/2012/189512. [PMID: 22518281]
  • Ramón Rodrigo. Prevention of postoperative atrial fibrillation: novel and safe strategy based on the modulation of the antioxidant system. Frontiers in physiology. 2012; 3(?):93. doi: 10.3389/fphys.2012.00093. [PMID: 22518106]
  • Barbara Dołęgowska, Wojciech Błogowski, Leszek Domański. Association between the perioperative antioxidative ability of platelets and early post-transplant function of kidney allografts: a pilot study. PloS one. 2012; 7(1):e29779. doi: 10.1371/journal.pone.0029779. [PMID: 22279544]
  • Raquel Martín-Venegas, Rosario Casillas, Olga Jáuregui, Juan José Moreno. Rapid simultaneous analysis of cyclooxygenase, lipoxygenase and cytochrome P-450 metabolites of arachidonic and linoleic acids using high performance liquid chromatography/mass spectrometry in tandem mode. Journal of pharmaceutical and biomedical analysis. 2011 Dec; 56(5):976-82. doi: 10.1016/j.jpba.2011.06.018. [PMID: 21880455]
  • Natalie C Ward, Kevin D Croft, David Blacker, Graeme J Hankey, Anne Barden, Trevor A Mori, Ian B Puddey, Christopher D Beer. Cytochrome P450 metabolites of arachidonic acid are elevated in stroke patients compared with healthy controls. Clinical science (London, England : 1979). 2011 Dec; 121(11):501-7. doi: 10.1042/cs20110215. [PMID: 21689071]
  • Giuseppe Vezzoli, Annalisa Terranegra, Francesco Rainone, Teresa Arcidiacono, Mario Cozzolino, Andrea Aloia, Elena Dogliotti, Daniele Cusi, Laura Soldati. Calcium-sensing receptor and calcium kidney stones. Journal of translational medicine. 2011 Nov; 9(?):201. doi: 10.1186/1479-5876-9-201. [PMID: 22107799]
  • 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: 10.1016/j.prostaglandins.2011.08.002. [PMID: 21856435]
  • Fumihiko Yoshino, Ayaka Yoshida, Naofumi Umigai, Koya Kubo, Masaichi-Chang-Il Lee. Crocetin reduces the oxidative stress induced reactive oxygen species in the stroke-prone spontaneously hypertensive rats (SHRSPs) brain. Journal of clinical biochemistry and nutrition. 2011 Nov; 49(3):182-7. doi: 10.3164/jcbn.11-01. [PMID: 22128217]
  • Cheng-Chia Wu, Michal Laniado Schwartzman. The role of 20-HETE in androgen-mediated hypertension. Prostaglandins & other lipid mediators. 2011 Nov; 96(1-4):45-53. doi: 10.1016/j.prostaglandins.2011.06.006. [PMID: 21722750]
  • Tengis S Pavlov, Daria V Ilatovskaya, Vladislav Levchenko, David L Mattson, Richard J Roman, Alexander Staruschenko. Effects of cytochrome P-450 metabolites of arachidonic acid on the epithelial sodium channel (ENaC). American journal of physiology. Renal physiology. 2011 Sep; 301(3):F672-81. doi: 10.1152/ajprenal.00597.2010. [PMID: 21697242]
  • Jatuporn Wichitsranoi, Natthida Weerapreeyakul, Patcharee Boonsiri, Chatri Settasatian, Nongnuch Settasatian, Nantarat Komanasin, Suchart Sirijaichingkul, Yaovalak Teerajetgul, Nuchanart Rangkadilok, Naruemon Leelayuwat. Antihypertensive and antioxidant effects of dietary black sesame meal in pre-hypertensive humans. Nutrition journal. 2011 Aug; 10(?):82. doi: 10.1186/1475-2891-10-82. [PMID: 21827664]
  • Howard Trachtman, Fernando C Fervenza, Debbie S Gipson, Peter Heering, David R W Jayne, Harm Peters, Stefano Rota, Giuseppe Remuzzi, L Christian Rump, Lorenz K Sellin, Jeremy P W Heaton, James B Streisand, Marjie L Hard, Steven R Ledbetter, Flavio Vincenti. A phase 1, single-dose study of fresolimumab, an anti-TGF-β antibody, in treatment-resistant primary focal segmental glomerulosclerosis. Kidney international. 2011 Jun; 79(11):1236-43. doi: 10.1038/ki.2011.33. [PMID: 21368745]
  • Licy L Yanes, Roberta Lima, Mohadetheh Moulana, Damian G Romero, Kuichang Yuan, Michael J Ryan, Rodney Baker, Huimin Zhang, Fan Fan, Deborah D Davis, Richard J Roman, Jane F Reckelhoff. Postmenopausal hypertension: role of 20-HETE. American journal of physiology. Regulatory, integrative and comparative physiology. 2011 Jun; 300(6):R1543-8. doi: 10.1152/ajpregu.00387.2010. [PMID: 21474427]
  • Alexandra Sporková, Libor Kopkan, Sárka Varcabová, Zuzana Husková, Sung Hee Hwang, Bruce D Hammock, John D Imig, Herbert J Kramer, Ludek Cervenka. Role of cytochrome P-450 metabolites in the regulation of renal function and blood pressure in 2-kidney 1-clip hypertensive rats. American journal of physiology. Regulatory, integrative and comparative physiology. 2011 Jun; 300(6):R1468-75. doi: 10.1152/ajpregu.00215.2010. [PMID: 21411763]
  • Kanyarat Boonprasert, Ronnatrai Ruengweerayut, Soisungwan Satarug, Kesara Na-Bangchang. Study on the association between environmental cadmium exposure, cytochrome P450-mediated 20-HETE, heme-oxygenase-1 polymorphism and hypertension in Thai population residing in a malaria endemic areas with cadmium pollution. Environmental toxicology and pharmacology. 2011 May; 31(3):416-26. doi: 10.1016/j.etap.2011.02.003. [PMID: 21787712]
  • I J Tsai, K D Croft, I B Puddey, L J Beilin, A Barden. 20-Hydroxyeicosatetraenoic acid synthesis is increased in human neutrophils and platelets by angiotensin II and endothelin-1. American journal of physiology. Heart and circulatory physiology. 2011 Apr; 300(4):H1194-200. doi: 10.1152/ajpheart.00733.2010. [PMID: 21239640]
  • M Kuczeriszka, K H Olszyński, A Gąsiorowska, J Sadowski, E Kompanowska-Jezierska. Interaction of nitric oxide and the cytochrome P-450 system on blood pressure and renal function in the rat: dependence on sodium intake. Acta physiologica (Oxford, England). 2011 Apr; 201(4):493-502. doi: 10.1111/j.1748-1716.2010.02222.x. [PMID: 21073660]
  • Bang-Chuan Hu, Yan Li, Fa-Hong Li, Yi Zhang, Chang-Sheng Sheng, Hong-Qi Fan, Ji-Guang Wang. Peripheral and central augmentation indexes in relation to the CYP4F2 polymorphisms in Chinese. Journal of hypertension. 2011 Mar; 29(3):501-8. doi: 10.1097/hjh.0b013e328342673c. [PMID: 21150635]
  • Joshua S Speed, Eric M George, Marietta Arany, Kathy Cockrell, Joey P Granger. Role of 20-hydroxyeicosatetraenoic acid in mediating hypertension in response to chronic renal medullary endothelin type B receptor blockade. PloS one. 2011; 6(10):e26063. doi: 10.1371/journal.pone.0026063. [PMID: 22016812]
  • Katherine N Theken, Yangmei Deng, M Alison Kannon, Tricia M Miller, Samuel M Poloyac, Craig R Lee. Activation of the acute inflammatory response alters cytochrome P450 expression and eicosanoid metabolism. Drug metabolism and disposition: the biological fate of chemicals. 2011 Jan; 39(1):22-9. doi: 10.1124/dmd.110.035287. [PMID: 20947618]
  • Antonio Cruz, Isabel Rodríguez-Gómez, Rocío Pérez-Abud, Miguel Ángel Vargas, Rosemary Wangensteen, Andrés Quesada, Antonio Osuna, Juan Manuel Moreno. Effects of clofibrate on salt loading-induced hypertension in rats. Journal of biomedicine & biotechnology. 2011; 2011(?):469481. doi: 10.1155/2011/469481. [PMID: 20981147]
  • Dexter L Lee, Justin L Wilson, Rong Duan, Tamaro Hudson, Ahmed El-Marakby. Peroxisome Proliferator-Activated Receptor-α Activation Decreases Mean Arterial Pressure, Plasma Interleukin-6, and COX-2 While Increasing Renal CYP4A Expression in an Acute Model of DOCA-Salt Hypertension. PPAR research. 2011; 2011(?):502631. doi: 10.1155/2011/502631. [PMID: 22190908]
  • Uwe Hoff, Ivo Lukitsch, Lyubov Chaykovska, Mechthild Ladwig, Cosima Arnold, Vijay L Manthati, T Florian Fuller, Wolfgang Schneider, Maik Gollasch, Dominik N Muller, Bert Flemming, Erdmann Seeliger, Friedrich C Luft, John R Falck, Duska Dragun, Wolf-Hagen Schunck. Inhibition of 20-HETE synthesis and action protects the kidney from ischemia/reperfusion injury. Kidney international. 2011 Jan; 79(1):57-65. doi: 10.1038/ki.2010.377. [PMID: 20962739]
  • Richard J Roman, Talha Akbulut, Frank Park, Kevin R Regner. 20-HETE in acute kidney injury. Kidney international. 2011 Jan; 79(1):10-3. doi: 10.1038/ki.2010.396. [PMID: 21157458]
  • Barbara Dolegowska, Wojciech Blogowski, Krzysztof Safranow, Leszek Domanski, Katarzyna Jakubowska, Maria Olszewska. Lipoxygenase-derived hydroxyeicosatetraenoic acids--novel perioperative markers of early post-transplant allograft function?. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2010 Dec; 25(12):4061-7. doi: 10.1093/ndt/gfq320. [PMID: 20530808]
  • Seyhan Sahan-Firat, Brett L Jennings, Fariborz A Yaghini, Chi Young Song, Anne M Estes, Xiao R Fang, Nasreen Farjana, Amir I Khan, Kafait U Malik. 2,3',4,5'-Tetramethoxystilbene prevents deoxycorticosterone-salt-induced hypertension: contribution of cytochrome P-450 1B1. American journal of physiology. Heart and circulatory physiology. 2010 Dec; 299(6):H1891-901. doi: 10.1152/ajpheart.00655.2010. [PMID: 20852048]
  • Dipak Panigrahy, Arja Kaipainen, Emily R Greene, Sui Huang. Cytochrome P450-derived eicosanoids: the neglected pathway in cancer. Cancer metastasis reviews. 2010 Dec; 29(4):723-35. doi: 10.1007/s10555-010-9264-x. [PMID: 20941528]
  • Xingbin Yang, Kevin D Croft, Ya P Lee, Trevor A Mori, Ian B Puddey, Sofia Sipsas, Anne Barden, Ewald Swinny, Jonathan M Hodgson. The effects of a lupin-enriched diet on oxidative stress and factors influencing vascular function in overweight subjects. Antioxidants & redox signaling. 2010 Nov; 13(10):1517-24. doi: 10.1089/ars.2010.3133. [PMID: 20214496]
  • Guillermo Suñé, Eduard Sarró, Marta Puigmulé, Joan López-Hellín, Madeleine Zufferey, Thomas Pertel, Jeremy Luban, Anna Meseguer. Cyclophilin B interacts with sodium-potassium ATPase and is required for pump activity in proximal tubule cells of the kidney. PloS one. 2010 Nov; 5(11):e13930. doi: 10.1371/journal.pone.0013930. [PMID: 21085665]
  • Bahar Tunctan, Belma Korkmaz, Tuba Cuez, C Kemal Buharalioglu, Seyhan Sahan-Firat, John Falck, Kafait U Malik. Contribution of vasoactive eicosanoids and nitric oxide production to the effect of selective cyclooxygenase-2 inhibitor, NS-398, on endotoxin-induced hypotension in rats. Basic & clinical pharmacology & toxicology. 2010 Nov; 107(5):877-82. doi: 10.1111/j.1742-7843.2010.00589.x. [PMID: 22545970]
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  • Philip R Cooper, A Clementina Mesaros, Jie Zhang, Peter Christmas, Christopher M Stark, Karim Douaidy, Michael A Mittelman, Roy J Soberman, Ian A Blair, Reynold A Panettieri. 20-HETE mediates ozone-induced, neutrophil-independent airway hyper-responsiveness in mice. PloS one. 2010 Apr; 5(4):e10235. doi: 10.1371/journal.pone.0010235. [PMID: 20422032]
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