5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid (BioDeep_00000594348)

   


代谢物信息卡片


5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid

化学式: C20H32O4 (336.2300472)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCC=CCC(C=CC=CC=CC(CCCC(=O)O)O)O
InChI: InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6+,14-10+,15-11+

描述信息

同义名列表

1 个代谢物同义名

5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid



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)

0 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

  • Larisse Ricardo Gadelha, Maria Juliana Bezerra Costa, João Paulo Alecrim de Abreu, Larissa Paola Rodrigues Venancio, Mary Hellen Fabres-Klein, Raphael Contelli Klein, Jonilson Berlink Lima, Théo Araújo-Santos. Prostaglandin E2/Leukotriene B4 balance and viral load in distinct clinical stages of COVID-19: A cross-sectional study. Prostaglandins & other lipid mediators. 2024 Jun; 172(?):106820. doi: 10.1016/j.prostaglandins.2024.106820. [PMID: 38346573]
  • Zumer Naeem, Sven Zukunft, Arnaud Huard, Jiong Hu, Bruce D Hammock, Andreas Weigert, Timo Frömel, Ingrid Fleming. Role of the soluble epoxide hydrolase in keratinocyte proliferation and sensitivity of skin to inflammatory stimuli. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2024 Jan; 171(?):116127. doi: 10.1016/j.biopha.2024.116127. [PMID: 38198951]
  • Amanda Brady, Katelyn R Sheneman, Amanda R Pulsifer, Sarah L Price, Taylor M Garrison, Krishna Rao Maddipati, Sobha R Bodduluri, Jianmin Pan, Nolan L Boyd, Jing-Juan Zheng, Shesh N Rai, Jason Hellmann, Bodduluri Haribabu, Silvia M Uriarte, Matthew B Lawrenz. Type 3 secretion system induced leukotriene B4 synthesis by leukocytes is actively inhibited by Yersinia pestis to evade early immune recognition. PLoS pathogens. 2024 Jan; 20(1):e1011280. doi: 10.1371/journal.ppat.1011280. [PMID: 38271464]
  • Jialu Chen, Yue Tang, Delong Qin, Xiaopeng Yu, Huanjun Tong, Chengwei Tang, Zhaohui Tang. ALOX5 acts as a key role in regulating the immune microenvironment in intrahepatic cholangiocarcinoma, recruiting tumor-associated macrophages through PI3K pathway. Journal of translational medicine. 2023 Dec; 21(1):923. doi: 10.1186/s12967-023-04804-1. [PMID: 38124204]
  • Riko Tatsumi, Saki Aihara, Seiya Matsune, Junken Aoki, Asuka Inoue, Takao Shimizu, Motonao Nakamura. Stepwise phosphorylation of BLT1 defines complex assemblies with β-arrestin serving distinct functions. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2023 Nov; 37(11):e23213. doi: 10.1096/fj.202301440r. [PMID: 37795742]
  • Mohsen Molaei, Ramin Lotfi, Reza Heidarymoghadam, Alireza Rezaiemanesh, Ali Gorgin Karaji, Farhad Salari. Imbalanced serum levels of resolvin E1 (RvE1) and leukotriene B4 (LTB4) may contribute to the pathogenesis of atherosclerosis. Prostaglandins & other lipid mediators. 2023 Sep; ?(?):106781. doi: 10.1016/j.prostaglandins.2023.106781. [PMID: 37704124]
  • Szimonetta Xénia Tamás, Benoit Thomas Roux, Boldizsár Vámosi, Fabian Gregor Dehne, Anna Török, László Fazekas, Balázs Enyedi. A genetically encoded sensor for visualizing leukotriene B4 gradients in vivo. Nature communications. 2023 08; 14(1):4610. doi: 10.1038/s41467-023-40326-6. [PMID: 37528073]
  • Motonao Nakamura, Takao Shimizu. Therapeutic target of leukotriene B4 receptors, BLT1 and BLT2: Insights from basic research. Biochimie. 2023 Jul; ?(?):. doi: 10.1016/j.biochi.2023.06.014. [PMID: 37423557]
  • Imen Ghzaiel, Amira Zarrouk, Vivien Pires, Jean-Paul Pais de Barros, Sonia Hammami, Mohamed Ksila, Mohamed Hammami, Taoufik Ghrairi, Pierre Jouanny, Anne Vejux, Gérard Lizard. 7β-Hydroxycholesterol and 7-ketocholesterol: New oxidative stress biomarkers of sarcopenia inducing cytotoxic effects on myoblasts and myotubes. The Journal of steroid biochemistry and molecular biology. 2023 Jun; 232(?):106345. doi: 10.1016/j.jsbmb.2023.106345. [PMID: 37286110]
  • Jie Tang, Ping Wu, Ze-Yun Yu, Xue Wang, Si-Yu Tao, Nan-Nan Jiang, Guan-Hua Chen, Rou-Xian Shuai. [Regulatory effect of moxibustion on LTB4/MMP-9 in serum of patients with rheumatoid arthritis]. Zhen ci yan jiu = Acupuncture research. 2023 May; 48(5):488-93. doi: 10.13702/j.1000-0607.20220088. [PMID: 37247863]
  • Chol Seung Lim, Brandon Veltri, Michael Kashon, Dale W Porter, Qiang Ma. Multi-walled carbon nanotubes induce arachidonate 5-lipoxygenase expression and enhance the polarization and function of M1 macrophages in vitro. Nanotoxicology. 2023 Apr; ?(?):1-21. doi: 10.1080/17435390.2023.2204161. [PMID: 37115655]
  • Xiaoxin Wu, Antonia RuJia Sun, Ross Crawford, Yin Xiao, Yanping Wang, Indira Prasadam, Xinzhan Mao. Inhibition of Leukotriene A4 Hydrolase Suppressed Cartilage Degradation and Synovial Inflammation in a Mouse Model of Experimental Osteoarthritis. Cartilage. 2023 Apr; ?(?):19476035231169940. doi: 10.1177/19476035231169940. [PMID: 37086004]
  • Takehiko Yokomizo, Takao Shimizu. The leukotriene B4 receptors BLT1 and BLT2 as potential therapeutic targets. Immunological reviews. 2023 Mar; ?(?):. doi: 10.1111/imr.13196. [PMID: 36908237]
  • Cristina Salinas-Nolasco, Gabriela Soledad Barragán-Zarate, Luicita Lagunez-Rivera, Rodolfo Solano, Liliana Favari, Juan Miguel Jiménez-Andrade, Aracely Evangelina Chávez-Piña. Role of LTB4 and nitric oxide in the gastroprotective effect of Prosthechea karwinskii leaves extract in the indomethacin-induced gastric injury in the rat. Natural product research. 2023 Mar; 37(5):819-822. doi: 10.1080/14786419.2022.2089880. [PMID: 35722687]
  • Ryotaro Shioda, Airi Jo-Watanabe, Toshiaki Okuno, Kazuko Saeki, Maiko Nakayama, Yusuke Suzuki, Takehiko Yokomizo. The leukotriene B4 /BLT1-dependent neutrophil accumulation exacerbates immune complex-mediated glomerulonephritis. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2023 02; 37(2):e22789. doi: 10.1096/fj.202201936r. [PMID: 36692419]
  • Changqing Sun, Wuyang Zheng, Ling Liang, Ziguan Zhang, Zuheng Liu, Wenchao Sun, Jianwei Zhou, Weitong Qiao, Qiang Xie, Rong Tang. Acute Coronary Syndrome May be Associated with Decreased Resolvin D1-to-Leukotriene B4 Ratio. International heart journal. 2023 Jan; ?(?):. doi: 10.1536/ihj.22-361. [PMID: 36682769]
  • Lauren E Hein, Shuvasree SenGupta, Gaurie Gunasekaran, Craig N Johnson, Carole A Parent. TGF-β1 activates neutrophil signaling and gene expression but not migration. PloS one. 2023; 18(9):e0290886. doi: 10.1371/journal.pone.0290886. [PMID: 37682817]
  • Amir A Razmjou, Jennifer M Wang, Ani Shahbazian, Srinivasa Reddy, Christina Charles-Schoeman. Suppressed paraoxonase-1 activity associates with elevated oxylipins and the presence of small airways disease in patients with rheumatoid arthritis. Clinical rheumatology. 2023 Jan; 42(1):75-82. doi: 10.1007/s10067-022-06375-w. [PMID: 36138190]
  • Letícia Paula Trajano Noronha, Monique Daiane Andrade Martins, Archimedes Barbosa Castro-Junior, Maria Luiza Thorstenberg, Laís Costa-Soares, Thuany Prado Rangel, Felipe Carvalho-Gondim, Bartira Rossi-Bergmann, Luiz Eduardo Baggio Savio, Claudio de Azevedo Canetti, Robson Coutinho-Silva. Cysteinyl-leukotrienes promote cutaneous Leishmaniasis control. Frontiers in cellular and infection microbiology. 2023; 13(?):1192800. doi: 10.3389/fcimb.2023.1192800. [PMID: 37377641]
  • Sourbh Suren Garg, Jeena Gupta, Debasis Sahu, Chuan-Ju Liu. Pharmacological and Therapeutic Applications of Esculetin. International journal of molecular sciences. 2022 Oct; 23(20):. doi: 10.3390/ijms232012643. [PMID: 36293500]
  • Berend Gagestein, Johannes H von Hegedus, Joanneke C Kwekkeboom, Marieke Heijink, Niek Blomberg, Tom van der Wel, Bogdan I Florea, Hans van den Elst, Kim Wals, Herman S Overkleeft, Martin Giera, René E M Toes, Andreea Ioan-Facsinay, Mario van der Stelt. Comparative Photoaffinity Profiling of Omega-3 Signaling Lipid Probes Reveals Prostaglandin Reductase 1 as a Metabolic Hub in Human Macrophages. Journal of the American Chemical Society. 2022 10; 144(41):18938-18947. doi: 10.1021/jacs.2c06827. [PMID: 36197299]
  • Motonao Nakamura, Takao Shimizu. Recent advances in function and structure of two leukotriene B4 receptors: BLT1 and BLT2. Biochemical pharmacology. 2022 09; 203(?):115178. doi: 10.1016/j.bcp.2022.115178. [PMID: 35850310]
  • Louise Ménégaut, Aline Laubriet, Valentin Crespy, Maxime Nguyen, Jean-Michel Petit, Georges Tarris, Thomas Pilot, Alexis Varin, Hélène Choubley, Victoria Bergas, Jean-Paul Pais de Barros, Charles Thomas, Eric Steinmetz, David Masson. Profiling of lipid mediators in atherosclerotic carotid plaques from type 2 diabetic and non-diabetic patients. Prostaglandins, leukotrienes, and essential fatty acids. 2022 09; 184(?):102477. doi: 10.1016/j.plefa.2022.102477. [PMID: 35952424]
  • Xingfeng Liu, Kai Wang, Luhai Wang, Lijuan Kong, Shaocong Hou, Yanjun Wan, Chunxiao Ma, Jingwen Chen, Xiaowei Xing, Caiyi Xing, Qian Jiang, Qijin Zhao, Bing Cui, Zhifeng Huang, Pingping Li. Hepatocyte leukotriene B4 receptor 1 promotes NAFLD development in obesity. Hepatology (Baltimore, Md.). 2022 Aug; ?(?):. doi: 10.1002/hep.32708. [PMID: 35931467]
  • Subhash B Arya, Song Chen, Fatima Jordan-Javed, Carole A Parent. Ceramide-rich microdomains facilitate nuclear envelope budding for non-conventional exosome formation. Nature cell biology. 2022 07; 24(7):1019-1028. doi: 10.1038/s41556-022-00934-8. [PMID: 35739317]
  • Yanfeng Li, Miaomiao Li, Rui Wang, Biyu Wang, Seyyed Shamsadin Athari, Jinli Wang. Ganoderma modulates allergic asthma pathologic features via anti-inflammatory effects. Respiratory physiology & neurobiology. 2022 05; 299(?):103843. doi: 10.1016/j.resp.2022.103843. [PMID: 35026480]
  • Jing Ruan, Chen Yang, Yali Du, Miao Chen, Bing Han. Plasma lipidome acts as diagnostic marker and predictor for cyclosporin response in patients with aplastic anemia. Clinical and experimental medicine. 2022 Apr; ?(?):. doi: 10.1007/s10238-022-00826-z. [PMID: 35445952]
  • Francine Lorencetti da Silva, Giuliana de Campos Chaves Lamarque, Fernanda Maria Machado Pereira Cabral de Oliveira, Paulo Nelson-Filho, Léa Assed Bezerra da Silva, Raquel Assed Bezerra Segato, Lúcia Helena Faccioli, Francisco Wanderley Garcia Paula-Silva. Leukotriene B4 loaded in microspheres regulate the expression of genes related to odontoblastic differentiation and biomineralization by dental pulp stem cells. BMC oral health. 2022 02; 22(1):45. doi: 10.1186/s12903-022-02083-8. [PMID: 35197043]
  • Miho Asahara, Nobuko Ito, Yoko Hoshino, Takaharu Sasaki, Takehiko Yokomizo, Motonao Nakamura, Takao Shimizu, Yoshitsugu Yamada. Role of leukotriene B4 (LTB4)-LTB4 receptor 1 signaling in post-incisional nociceptive sensitization and local inflammation in mice. PloS one. 2022; 17(10):e0276135. doi: 10.1371/journal.pone.0276135. [PMID: 36264904]
  • Olga V Belyaeva, Samuel E Wirth, William E Boeglin, Suman Karki, Kelli R Goggans, Stacy G Wendell, Kirill M Popov, Alan R Brash, Natalia Y Kedishvili. Dehydrogenase reductase 9 (SDR9C4) and related homologs recognize a broad spectrum of lipid mediator oxylipins as substrates. The Journal of biological chemistry. 2022 01; 298(1):101527. doi: 10.1016/j.jbc.2021.101527. [PMID: 34953854]
  • Jiheng Hao, Yao Feng, Xin Xu, Long Li, Kun Yang, Gaolei Dai, Weiwei Gao, Meng Zhang, Yaming Fan, Tengkun Yin, Jiyue Wang, Bin Yang, Liqun Jiao, Liyong Zhang. Plasma Lipid Mediators Associate With Clinical Outcome After Successful Endovascular Thrombectomy in Patients With Acute Ischemic Stroke. Frontiers in immunology. 2022; 13(?):917974. doi: 10.3389/fimmu.2022.917974. [PMID: 35865524]
  • Luiza Oliveira Perucci, Kelerson Mauro de Castro Pinto, Sirlaine Pio Gomes da Silva, Eura Martins Lage, Patrícia Gonçalves Teixeira, Alexandre Simões Barbosa, Patrícia Nessralla Alpoim, Lirlândia Pires de Sousa, André Talvani, Luci Maria SantAna Dusse. Longitudinal assessment of leukotriene B4, lipoxin A4, and resolvin D1 plasma levels in pregnant women with risk factors for preeclampsia. Clinical biochemistry. 2021 Dec; 98(?):24-28. doi: 10.1016/j.clinbiochem.2021.09.002. [PMID: 34492288]
  • Pallavi Bedi, Kerstin Ziegler, Phil D Whitfield, Donald Davidson, Adriano Giorgio Rossi, Adam T Hill. Dysregulation of prostaglandins, leukotrienes and lipoxin A4 in bronchiectasis. Thorax. 2021 Nov; ?(?):. doi: 10.1136/thoraxjnl-2020-216475. [PMID: 34789559]
  • Mélissa Simard, Geneviève Rioux, Sophie Morin, Cyril Martin, Sylvain L Guérin, Nicolas Flamand, Pierre Julien, Julie Fradette, Roxane Pouliot. Investigation of Omega-3 Polyunsaturated Fatty Acid Biological Activity in a Tissue-Engineered Skin Model Involving Psoriatic Cells. The Journal of investigative dermatology. 2021 10; 141(10):2391-2401.e13. doi: 10.1016/j.jid.2021.02.755. [PMID: 33857488]
  • Heeju Lee, Bora Lee, Yeonhee Kim, Sohyun Min, Eunjoo Yang, Seungmin Lee. Effects of Sodium Selenite Injection on Serum Metabolic Profiles in Women Diagnosed with Breast Cancer-Related Lymphedema-Secondary Analysis of a Randomized Placebo-Controlled Trial Using Global Metabolomics. Nutrients. 2021 Sep; 13(9):. doi: 10.3390/nu13093253. [PMID: 34579131]
  • Tatsuro Nakamura. The roles of lipid mediators in type I hypersensitivity. Journal of pharmacological sciences. 2021 Sep; 147(1):126-131. doi: 10.1016/j.jphs.2021.06.001. [PMID: 34294363]
  • Anne-Sophie Archambault, Younes Zaid, Volatiana Rakotoarivelo, Caroline Turcotte, Étienne Doré, Isabelle Dubuc, Cyril Martin, Olivier Flamand, Youssef Amar, Amine Cheikh, Hakima Fares, Amine El Hassani, Youssef Tijani, Andréanne Côté, Michel Laviolette, Éric Boilard, Louis Flamand, Nicolas Flamand. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2021 06; 35(6):e21666. doi: 10.1096/fj.202100540r. [PMID: 34033145]
  • Francine K Welty, Fabian Schulte, Abdulhamied Alfaddagh, Tarec K Elajami, Bruce R Bistrian, Markus Hardt. Regression of human coronary artery plaque is associated with a high ratio of (18-hydroxy-eicosapentaenoic acid + resolvin E1) to leukotriene B4. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2021 04; 35(4):e21448. doi: 10.1096/fj.202002471r. [PMID: 33749913]
  • Meng Yuan, Yue Zhang, Tong Hua, Xiang-Li Liu, Tong Liu, Ru-Yu Yuan, Guang-Ping Li, Yi Zhu, Xu Zhang. Omega-3 polyunsaturated fatty acid supplementation improves lipid metabolism and endothelial function by providing a beneficial eicosanoid-pattern in patients with acute myocardial infarction: A randomized, controlled trial. Clinical nutrition (Edinburgh, Scotland). 2021 02; 40(2):445-459. doi: 10.1016/j.clnu.2020.05.034. [PMID: 33041091]
  • Toshiaki Okuno, Takehiko Yokomizo. Metabolism and biological functions of 12(S)-hydroxyheptadeca-5Z,8E,10E-trienoic acid. Prostaglandins & other lipid mediators. 2021 02; 152(?):106502. doi: 10.1016/j.prostaglandins.2020.106502. [PMID: 33075476]
  • Lifeng Yang, Jyunichi Kirikoshi, Daiki Sato, Mikako Takasugi, Atsuyuki Hishida, Shigeki Hayashi, Nobuo Kawahara, Megumi Mizukami, Maoyu Wu, Takashi Yamagishi, Hirofumi Arai. New isoflavone glucosides in yabumame (Amphicarpaea bracteata (L.) Fernald subsp. edgeworthii (Benth.) H.Ohashi var. japonica (Oliv.) H.Ohashi) and their effect on leukotriene B4 production in mast cells. Journal of natural medicines. 2021 Jan; 75(1):28-36. doi: 10.1007/s11418-020-01439-0. [PMID: 32803653]
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  • Carlos A Penno, Petra Jäger, Claire Laguerre, Franziska Hasler, Andreas Hofmann, Stephanie K Gass, Barbara Wettstein-Ling, Dirk J Schaefer, Alexandre Avrameas, Friedrich Raulf, Grazyna Wieczorek, Joachim C U Lehmann, Christian Loesche, Lukas Roth, Till A Röhn. Lipidomics Profiling of Hidradenitis Suppurativa Skin Lesions Reveals Lipoxygenase Pathway Dysregulation and Accumulation of Proinflammatory Leukotriene B4. The Journal of investigative dermatology. 2020 12; 140(12):2421-2432.e10. doi: 10.1016/j.jid.2020.04.011. [PMID: 32387270]
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