5-KETE (BioDeep_00000003306)

 

Secondary id: BioDeep_00000397613

human metabolite Endogenous blood metabolite


代谢物信息卡片


(6E,8Z,11Z,14Z)-5-oxoicosa-6,8,11,14-tetraenoic acid

化学式: C20H30O3 (318.219483)
中文名称: 5-氧代-二十烷四烯酸
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.13%

Reviewed

Last reviewed on 2024-10-24.

Cite this Page

5-KETE. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/5-kete (retrieved 2024-11-08) (BioDeep RN: BioDeep_00000003306). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(O)(=O)CCCC(=O)/C=C/C=C\C/C=C\C/C=C\CCCCC
InChI: InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+

描述信息

5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-oxo-ETE), 5-lipoxygenase product is a potent chemoattractant for neutrophils and eosinophils. Its actions are mediated by the oxoeicosanoid (OXE) receptor, a member of the G protein-coupled receptor family.(PMID:18292294) [HMDB]
5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-oxo-ETE), 5-lipoxygenase product is a potent chemoattractant for neutrophils and eosinophils. Its actions are mediated by the oxoeicosanoid (OXE) receptor, a member of the G protein-coupled receptor family.(PMID:18292294).

同义名列表

30 个代谢物同义名

5-oxo-6,8,11,14-Eicosatetraenoic acid, e,Z,Z,Z isomer; (6E,8Z,11Z,14Z)-5-Oxoicosa-6,8,11,14-tetraenoic acid; 5-oxo-6(e),8(Z),11(Z),14(Z)-Eicosatetraenoic acid; (6E,8Z,11Z,14Z)-5-Oxoicosa-6,8,11,14-tetraenoate; 5-oxo-6(e),8(Z),11(Z),14(Z)-Eicosatetraenoate; 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid; 5-Keto-6,8,11,14-eicosatetraenoic acid; 5-oxo-Icosa-6,8,11,14-tetraenoic acid; 5-oxo-6,8,11,14-Eicosatetraenoic acid; 5-oxo-6E,8Z,11Z,14Z-Eicosatetraenoate; 5-Keto-6,8,11,14-eicosatetraenoate; 5-oxo-Icosa-6,8,11,14-tetraenoate; 5-oxo-6,8,11,14-Eicosatetraenoate; Eicosa-5,8,12,14-tetraenoic acid; Eicosa-5,8,12,14-tetraenoate; 5-oxo-Eicosatetraenoic acid; 5-Ketoeicosatetraenoic acid; 5-Oxoeicosatetraenoic acid; 5-oxo, 6t,8C,11C,14C-20:4; 5-Oxoicosatetraenoic acid; 5-Ketoeicosatetraenoate; 5-oxo-Eicosatetraenoate; 5-Oxoeicosatetraenoate; 5-Oxoicosatetraenoate; 5-oxo-6,8,11,14-ETE; 5-Keto-ete; FA 20:5;O; 5-Oxo-ETE; 5-Oxoete; 5-KETE



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(10)

BioCyc(0)

PlantCyc(0)

代谢反应

79 个相关的代谢反应过程信息。

Reactome(31)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(46)

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。



文献列表

  • Kenneth D Maus, Daniel J Stephenson, Anika N Ali, Henry Patrick MacKnight, Huey-Jing Huang, Jordi Serrats, Minjung Kim, Robert F Diegelmann, Charles E Chalfant. Ceramide kinase regulates acute wound healing by suppressing 5-oxo-ETE biosynthesis and signaling via its receptor OXER1. Journal of lipid research. 2022 04; 63(4):100187. doi: 10.1016/j.jlr.2022.100187. [PMID: 35219746]
  • Roxana Coras, Arthur Kavanaugh, Angela Kluzniak, Dustina Holt, Amy Weilgosz, Armando Aaron, Oswald Quehenberger, Christopher Ritchlin, Monica Guma. Differences in oxylipin profile in psoriasis versus psoriatic arthritis. Arthritis research & therapy. 2021 07; 23(1):200. doi: 10.1186/s13075-021-02575-y. [PMID: 34303373]
  • Qiong Lai, Guangying Yuan, Le Shen, Lu Zhang, Fei Fu, Zeliang Liu, Yuanyuan Zhang, Junping Kou, Shijia Liu, Boyang Yu, Fang Li. Oxoeicosanoid receptor inhibition alleviates acute myocardial infarction through activation of BCAT1. Basic research in cardiology. 2021 01; 116(1):3. doi: 10.1007/s00395-021-00844-0. [PMID: 33484341]
  • Natalia Celejewska-Wójcik, Aleksander Kania, Karolina Górka, Paweł Nastałek, Krzysztof Wójcik, Anna Gielicz, Lucyna Mastalerz, Marek Sanak, Krzysztof Sładek. Eicosanoids and Eosinophilic Inflammation of Airways in Stable COPD. International journal of chronic obstructive pulmonary disease. 2021 ; 16(?):1415-1424. doi: 10.2147/copd.s298678. [PMID: 34079245]
  • William S Powell, Joshua Rokach. Targeting the OXE receptor as a potential novel therapy for asthma. Biochemical pharmacology. 2020 09; 179(?):113930. doi: 10.1016/j.bcp.2020.113930. [PMID: 32240653]
  • Marcin Banaszczak, Dominika Maciejewska, Arleta Drozd, Karina Ryterska, Dominika Jamioł Milc, Joanna Raszeja-Wyszomirska, Ewa Wunsch, Pedro González-Muniesa, Ewa Stachowska. 5-Lipooxygenase Derivatives as Serum Biomarkers of a Successful Dietary Intervention in Patients with NonAlcoholic Fatty Liver Disease. Medicina (Kaunas, Lithuania). 2020 Feb; 56(2):. doi: 10.3390/medicina56020058. [PMID: 32028646]
  • Lisa A Miller, Chantal Cossette, Shishir Chourey, Qiuji Ye, Chintam Nagendra Reddy, Joshua Rokach, William S Powell. Inhibition of allergen-induced dermal eosinophilia by an oxoeicosanoid receptor antagonist in non-human primates. British journal of pharmacology. 2020 01; 177(2):360-371. doi: 10.1111/bph.14872. [PMID: 31655023]
  • Marcin Surmiak, Anna Gielicz, Darko Stojkov, Rafał Szatanek, Katarzyna Wawrzycka-Adamczyk, Shida Yousefi, Hans-Uwe Simon, Marek Sanak. LTB4 and 5-oxo-ETE from extracellular vesicles stimulate neutrophils in granulomatosis with polyangiitis. Journal of lipid research. 2020 01; 61(1):1-9. doi: 10.1194/jlr.m092072. [PMID: 31740445]
  • Isabel Neuman, Mariana Cooke, Nicolás Agustín Lemiña, Marcelo G Kazanietz, Fabiana Cornejo Maciel. 5-oxo-ETE activates migration of H295R adrenocortical cells via MAPK and PKC pathways. Prostaglandins & other lipid mediators. 2019 10; 144(?):106346. doi: 10.1016/j.prostaglandins.2019.106346. [PMID: 31301403]
  • Shishir Chourey, Qiuji Ye, Chintam Nagendra Reddy, Rui Wang, Chantal Cossette, Sylvie Gravel, Irina Slobodchikova, Dajana Vuckovic, Joshua Rokach, William S Powell. Novel Highly Potent and Metabolically Resistant Oxoeicosanoid (OXE) Receptor Antagonists That Block the Actions of the Granulocyte Chemoattractant 5-Oxo-6,8,11,14-Eicosatetraenoic Acid (5-oxo-ETE). Journal of medicinal chemistry. 2018 Jul; 61(14):5934-5948. doi: 10.1021/acs.jmedchem.8b00154. [PMID: 29972644]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Chintam Nagendra Reddy, Hussam Alhamza, Shishir Chourey, Qiuji Ye, Vivek Gore, Chantal Cossette, Sylvie Gravel, Irina Slobodchikova, Dajana Vuckovic, Joshua Rokach, William S Powell. Metabolism and pharmacokinetics of a potent N-acylindole antagonist of the OXE receptor for the eosinophil chemoattractant 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) in rats and monkeys. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2018 Mar; 115(?):88-99. doi: 10.1016/j.ejps.2018.01.021. [PMID: 29339225]
  • Lin Lin, Zheng Chen, Xinyue Tang, Fei Dai, Jinjin Wei, Guangbin Sun. 5-Oxo-ETE from Nasal Epithelial Cells Upregulates Eosinophil Cation Protein by Eosinophils in Nasal Polyps in vitro. International archives of allergy and immunology. 2018 ; 177(2):107-115. doi: 10.1159/000489819. [PMID: 29898459]
  • Shishir Chourey, Qiuji Ye, Chintam Nagendra Reddy, Chantal Cossette, Sylvie Gravel, Matthias Zeller, Irina Slobodchikova, Dajana Vuckovic, Joshua Rokach, William S Powell. In vivo α-hydroxylation of a 2-alkylindole antagonist of the OXE receptor for the eosinophil chemoattractant 5-oxo-6,8,11,14-eicosatetraenoic acid in monkeys. Biochemical pharmacology. 2017 08; 138(?):107-118. doi: 10.1016/j.bcp.2017.04.031. [PMID: 28476332]
  • Chantal Cossette, Shishir Chourey, Qiuji Ye, Chintam Nagendra Reddy, Vivek Gore, Sylvie Gravel, Irina Slobodchikova, Dajana Vuckovic, Joshua Rokach, William S Powell. Pharmacokinetics and Metabolism of Selective Oxoeicosanoid (OXE) Receptor Antagonists and Their Effects on 5-Oxo-6,8,11,14-eicosatetraenoic Acid (5-Oxo-ETE)-Induced Granulocyte Activation in Monkeys. Journal of medicinal chemistry. 2016 11; 59(22):10127-10146. doi: 10.1021/acs.jmedchem.6b00895. [PMID: 27766872]
  • Chantal Cossette, Sylvie Gravel, Chintam Nagendra Reddy, Vivek Gore, Shishir Chourey, Qiuji Ye, Nathaniel W Snyder, Clementina A Mesaros, Ian A Blair, Jean-Pierre Lavoie, Carol R Reinero, Joshua Rokach, William S Powell. Biosynthesis and actions of 5-oxoeicosatetraenoic acid (5-oxo-ETE) on feline granulocytes. Biochemical pharmacology. 2015 Aug; 96(3):247-55. doi: 10.1016/j.bcp.2015.05.009. [PMID: 26032638]
  • William S Powell, Joshua Rokach. Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid. Biochimica et biophysica acta. 2015 Apr; 1851(4):340-55. doi: 10.1016/j.bbalip.2014.10.008. [PMID: 25449650]
  • E Stachowska, D Maciejewska, P Ossowski, A Drozd, K Ryterska, M Banaszczak, M Milkiewicz, J Raszeja-Wyszomirska, M Slebioda, P Milkiewicz, H Jelen. Apolipoprotein E4 allele is associated with substantial changes in the plasma lipids and hyaluronic acid content in patients with nonalcoholic fatty liver disease. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society. 2013 Dec; 64(6):711-7. doi: NULL. [PMID: 24388885]
  • William S Powell, Joshua Rokach. The eosinophil chemoattractant 5-oxo-ETE and the OXE receptor. Progress in lipid research. 2013 Oct; 52(4):651-65. doi: 10.1016/j.plipres.2013.09.001. [PMID: 24056189]
  • Vivek Gore, Pranav Patel, Chih-Tsung Chang, Sashikala Sivendran, Namin Kang, Yannick P Ouedraogo, Sylvie Gravel, William S Powell, Joshua Rokach. 5-Oxo-ETE receptor antagonists. Journal of medicinal chemistry. 2013 May; 56(9):3725-32. doi: 10.1021/jm400480j. [PMID: 23581530]
  • Jun Miyata, Koichi Fukunaga, Ryo Iwamoto, Yosuke Isobe, Kyoko Niimi, Rina Takamiya, Takahisa Takihara, Katsuyoshi Tomomatsu, Yusuke Suzuki, Tsuyoshi Oguma, Koichi Sayama, Hiroyuki Arai, Tomoko Betsuyaku, Makoto Arita, Koichiro Asano. Dysregulated synthesis of protectin D1 in eosinophils from patients with severe asthma. The Journal of allergy and clinical immunology. 2013 Feb; 131(2):353-60.e1. doi: 10.1016/j.jaci.2012.07.048. [PMID: 23006546]
  • Tatiana A Karelina, Kirill V Zhudenkov, Oleg O Demin, Dmitry V Svetlichny, Balaji Agoram, David Fairman, Oleg V Demin. Regulation of leukotriene and 5oxoETE synthesis and the effect of 5-lipoxygenase inhibitors: a mathematical modeling approach. BMC systems biology. 2012 Nov; 6(?):141. doi: 10.1186/1752-0509-6-141. [PMID: 23146124]
  • Charles B Stephensen, Patrice Armstrong, John W Newman, Theresa L Pedersen, Jillian Legault, Gertrud U Schuster, Darshan Kelley, Susanna Vikman, Jaana Hartiala, Rami Nassir, Michael F Seldin, Hooman Allayee. ALOX5 gene variants affect eicosanoid production and response to fish oil supplementation. Journal of lipid research. 2011 May; 52(5):991-1003. doi: 10.1194/jlr.p012864. [PMID: 21296957]
  • Dong-Soon Im. New intercellular lipid mediators and their GPCRs: an update. Prostaglandins & other lipid mediators. 2009 Sep; 89(3-4):53-6. doi: 10.1016/j.prostaglandins.2009.01.002. [PMID: 19442546]
  • Gail E Grant, Joshua Rokach, William S Powell. 5-Oxo-ETE and the OXE receptor. Prostaglandins & other lipid mediators. 2009 Sep; 89(3-4):98-104. doi: 10.1016/j.prostaglandins.2009.05.002. [PMID: 19450703]
  • Caroline Morin, Marco Sirois, Vincent Echave, Marcio M Gomes, Eric Rousseau. Relaxing effects of 5-oxo-ETE on human bronchi involve BK Ca channel activation. Prostaglandins & other lipid mediators. 2007 Jun; 83(4):311-9. doi: 10.1016/j.prostaglandins.2007.03.001. [PMID: 17499751]
  • Paul Rubin, Karl W Mollison. Pharmacotherapy of diseases mediated by 5-lipoxygenase pathway eicosanoids. Prostaglandins & other lipid mediators. 2007 May; 83(3):188-97. doi: 10.1016/j.prostaglandins.2007.01.005. [PMID: 17481554]
  • Karl-Rudolf Erlemann, Chantal Cossette, Sylvie Gravel, Alain Lesimple, Gue-Jae Lee, Goutam Saha, Joshua Rokach, William S Powell. Airway epithelial cells synthesize the lipid mediator 5-oxo-ETE in response to oxidative stress. Free radical biology & medicine. 2007 Mar; 42(5):654-64. doi: 10.1016/j.freeradbiomed.2006.12.006. [PMID: 17291989]
  • Caroline Morin, Eric Rousseau. Effects of 5-oxo-ETE and 14,15-EET on reactivity and Ca2+ sensitivity in guinea pig bronchi. Prostaglandins & other lipid mediators. 2007 Jan; 82(1-4):30-41. doi: 10.1016/j.prostaglandins.2006.05.012. [PMID: 17164130]
  • Petra Schratl, Eva M Sturm, Julia F Royer, Gunter J Sturm, Irmgard T Lippe, Bernhard A Peskar, Akos Heinemann. Hierarchy of eosinophil chemoattractants: role of p38 mitogen-activated protein kinase. European journal of immunology. 2006 Sep; 36(9):2401-9. doi: 10.1002/eji.200535672. [PMID: 16906532]
  • William S Powell, Joshua Rokach. Biochemistry, biology and chemistry of the 5-lipoxygenase product 5-oxo-ETE. Progress in lipid research. 2005 Mar; 44(2-3):154-83. doi: 10.1016/j.plipres.2005.04.002. [PMID: 15893379]
  • Panagiota B Stamatiou, Chi-Chung Chan, Guillaume Monneret, Diane Ethier, Joshua Rokach, William S Powell. 5-oxo-6,8,11,14-eicosatetraenoic acid stimulates the release of the eosinophil survival factor granulocyte/macrophage colony-stimulating factor from monocytes. The Journal of biological chemistry. 2004 Jul; 279(27):28159-64. doi: 10.1074/jbc.m401537200. [PMID: 15136573]
  • Francis Davoine, Isabelle Labonté, Claudine Ferland, Bruce Mazer, Jamila Chakir, Michel Laviolette. Role and modulation of CD16 expression on eosinophils by cytokines and immune complexes. International archives of allergy and immunology. 2004 Jun; 134(2):165-72. doi: 10.1159/000078650. [PMID: 15153797]
  • Evi Kostenis. A glance at G-protein-coupled receptors for lipid mediators: a growing receptor family with remarkably diverse ligands. Pharmacology & therapeutics. 2004 Jun; 102(3):243-57. doi: 10.1016/j.pharmthera.2004.04.005. [PMID: 15246248]
  • Simona Zarini, Robert C Murphy. Biosynthesis of 5-oxo-6,8,11,14-eicosatetraenoic acid from 5-hydroperoxyeicosatetraenoic acid in the murine macrophage. The Journal of biological chemistry. 2003 Mar; 278(13):11190-6. doi: 10.1074/jbc.m208496200. [PMID: 12547823]
  • Takeshi Hosoi, Yutaka Koguchi, Emiko Sugikawa, Aiko Chikada, Koji Ogawa, Naoki Tsuda, Naoki Suto, Shiho Tsunoda, Tomoyasu Taniguchi, Tetsuo Ohnuki. Identification of a novel human eicosanoid receptor coupled to G(i/o). The Journal of biological chemistry. 2002 Aug; 277(35):31459-65. doi: 10.1074/jbc.m203194200. [PMID: 12065583]
  • Robert C Murphy, Simona Zarini. Glutathione adducts of oxyeicosanoids. Prostaglandins & other lipid mediators. 2002 Aug; 68-69(?):471-82. doi: 10.1016/s0090-6980(02)00049-7. [PMID: 12432937]
  • C Ferland, M Guilbert, F Davoine, N Flamand, J Chakir, M Laviolette. Eotaxin promotes eosinophil transmigration via the activation of the plasminogen-plasmin system. Journal of leukocyte biology. 2001 May; 69(5):772-8. doi: NULL. [PMID: 11358986]
  • W S Powell, S Ahmed, S Gravel, J Rokach. Eotaxin and RANTES enhance 5-oxo-6,8,11,14-eicosatetraenoic acid-induced eosinophil chemotaxis. The Journal of allergy and clinical immunology. 2001 Feb; 107(2):272-8. doi: 10.1067/mai.2001.112847. [PMID: 11174193]
  • W S Powell, S Gravel, F Halwani. 5-oxo-6,8,11,14-eicosatetraenoic acid is a potent stimulator of L-selectin shedding, surface expression of CD11b, actin polymerization, and calcium mobilization in human eosinophils. American journal of respiratory cell and molecular biology. 1999 Jan; 20(1):163-70. doi: 10.1165/ajrcmb.20.1.3141. [PMID: 9870930]
  • J T O'Flaherty, J S Taylor, M J Thomas. Receptors for the 5-oxo class of eicosanoids in neutrophils. The Journal of biological chemistry. 1998 Dec; 273(49):32535-41. doi: 10.1074/jbc.273.49.32535. [PMID: 9829988]
  • L M Hall, R C Murphy. Activation of human polymorphonuclear leukocytes by products derived from the peroxidation of human red blood cell membranes. Chemical research in toxicology. 1998 Sep; 11(9):1024-31. doi: 10.1021/tx9801155. [PMID: 9760276]
  • W S Powell, S Gravel, F Halwani, C S Hii, Z H Huang, A M Tan, A Ferrante. Effects of 5-oxo-6,8,11,14-eicosatetraenoic acid on expression of CD11b, actin polymerization, and adherence in human neutrophils. Journal of immunology (Baltimore, Md. : 1950). 1997 Sep; 159(6):2952-9. doi: . [PMID: 9300719]
  • W S Powell, D Chung, S Gravel. 5-Oxo-6,8,11,14-eicosatetraenoic acid is a potent stimulator of human eosinophil migration. Journal of immunology (Baltimore, Md. : 1950). 1995 Apr; 154(8):4123-32. doi: . [PMID: 7706749]
  • W S Powell, F Gravelle, S Gravel. Phorbol myristate acetate stimulates the formation of 5-oxo-6,8,11,14-eicosatetraenoic acid by human neutrophils by activating NADPH oxidase. The Journal of biological chemistry. 1994 Oct; 269(41):25373-80. doi: . [PMID: 7929234]
  • W S Powell, F Gravelle, S Gravel, M Hashefi. Metabolism of 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human neutrophils. Journal of lipid mediators. 1993 Mar; 6(1-3):361-8. doi: . [PMID: 8395251]
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