(12S)-12-Hydroxyicosa-2,4,6,8-tetraenoic acid (BioDeep_00000171564)

   

human metabolite blood metabolite


代谢物信息卡片


(12S)-12-Hydroxyicosa-2,4,6,8-tetraenoic acid

化学式: C20H32O3 (320.23513219999995)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 87.5%

分子结构信息

SMILES: CCCCCCCCC(O)CCC=CC=CC=CC=CC(O)=O
InChI: InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h6-9,11-12,15,18-19,21H,2-5,10,13-14,16-17H2,1H3,(H,22,23)



数据库引用编号

3 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。



文献列表

  • Mohamad Navab, Srinivasa T Reddy, Brian J Van Lenten, Georgette M Buga, Greg Hough, Alan C Wagner, Alan M Fogelman. High-density lipoprotein and 4F peptide reduce systemic inflammation by modulating intestinal oxidized lipid metabolism: novel hypotheses and review of literature. Arteriosclerosis, thrombosis, and vascular biology. 2012 Nov; 32(11):2553-60. doi: 10.1161/atvbaha.112.300282. [PMID: 23077141]
  • Jessica R Weaver, Theodore R Holman, Yumi Imai, Ajit Jadhav, Victor Kenyon, David J Maloney, Jerry L Nadler, Ganesha Rai, Anton Simeonov, David A Taylor-Fishwick. Integration of pro-inflammatory cytokines, 12-lipoxygenase and NOX-1 in pancreatic islet beta cell dysfunction. Molecular and cellular endocrinology. 2012 Jul; 358(1):88-95. doi: 10.1016/j.mce.2012.03.004. [PMID: 22502743]
  • Naoki Tanaka, Tsutomu Matsubara, Kristopher W Krausz, Andrew D Patterson, Frank J Gonzalez. Disruption of phospholipid and bile acid homeostasis in mice with nonalcoholic steatohepatitis. Hepatology (Baltimore, Md.). 2012 Jul; 56(1):118-29. doi: 10.1002/hep.25630. [PMID: 22290395]
  • Katharina Sterz, Gerhard Scherer, Josef Ecker. A simple and robust UPLC-SRM/MS method to quantify urinary eicosanoids. Journal of lipid research. 2012 May; 53(5):1026-1036. doi: 10.1194/jlr.d023739. [PMID: 22338011]
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  • Chaoqin Xie, Donna H Wang. Inhibition of renin release by arachidonic acid metabolites, 12(s)-HPETE and 12-HETE: role of TRPV1 channels. Endocrinology. 2011 Oct; 152(10):3811-9. doi: 10.1210/en.2011-0141. [PMID: 21846804]
  • Asaf A Qureshi, Charles W Karpen, Nilofer Qureshi, Christopher J Papasian, David C Morrison, John D Folts. Tocotrienols-induced inhibition of platelet thrombus formation and platelet aggregation in stenosed canine coronary arteries. Lipids in health and disease. 2011 Apr; 10(?):58. doi: 10.1186/1476-511x-10-58. [PMID: 21489303]
  • Jérôme Bellenger, Sandrine Bellenger, Amandine Bataille, Karen A Massey, Anna Nicolaou, Mickaël Rialland, Christian Tessier, Jing X Kang, Michel Narce. High pancreatic n-3 fatty acids prevent STZ-induced diabetes in fat-1 mice: inflammatory pathway inhibition. Diabetes. 2011 Apr; 60(4):1090-9. doi: 10.2337/db10-0901. [PMID: 21330635]
  • Beate Gomolka, Elise Siegert, Katrin Blossey, Wolf-Hagen Schunck, Michael Rothe, Karsten H Weylandt. Analysis of omega-3 and omega-6 fatty acid-derived lipid metabolite formation in human and mouse blood samples. Prostaglandins & other lipid mediators. 2011 Apr; 94(3-4):81-7. doi: 10.1016/j.prostaglandins.2010.12.006. [PMID: 21236358]
  • Jun Ma, Lynetta Phillips, Ying Wang, Tiane Dai, Janine LaPage, Rama Natarajan, Sharon G Adler. Curcumin activates the p38MPAK-HSP25 pathway in vitro but fails to attenuate diabetic nephropathy in DBA2J mice despite urinary clearance documented by HPLC. BMC complementary and alternative medicine. 2010 Nov; 10(?):67. doi: 10.1186/1472-6882-10-67. [PMID: 21073732]
  • Haibin Tian, Yan Lu, Shraddha P Shah, Song Hong. Novel 14S,21-dihydroxy-docosahexaenoic acid rescues wound healing and associated angiogenesis impaired by acute ethanol intoxication/exposure. Journal of cellular biochemistry. 2010 Oct; 111(2):266-73. doi: 10.1002/jcb.22709. [PMID: 20506249]
  • Yael Riahi, Yoav Sin-Malia, Guy Cohen, Evgenia Alpert, Arie Gruzman, Juergen Eckel, Bart Staels, Michel Guichardant, Shlomo Sasson. The natural protective mechanism against hyperglycemia in vascular endothelial cells: roles of the lipid peroxidation product 4-hydroxydodecadienal and peroxisome proliferator-activated receptor delta. Diabetes. 2010 Apr; 59(4):808-18. doi: 10.2337/db09-1207. [PMID: 20107107]
  • Lide Arana, Patricia Gangoiti, Alberto Ouro, Miguel Trueba, Antonio Gómez-Muñoz. Ceramide and ceramide 1-phosphate in health and disease. Lipids in health and disease. 2010 Feb; 9(?):15. doi: 10.1186/1476-511x-9-15. [PMID: 20137073]
  • Hiromi Ii, Naoki Yokoyama, Shintaro Yoshida, Kae Tsutsumi, Shinji Hatakeyama, Takashi Sato, Keiichi Ishihara, Satoshi Akiba. Alleviation of high-fat diet-induced fatty liver damage in group IVA phospholipase A2-knockout mice. PloS one. 2009 Dec; 4(12):e8089. doi: 10.1371/journal.pone.0008089. [PMID: 19956652]
  • Alwena H Morgan, Vincent Dioszeghy, Benjamin H Maskrey, Christopher P Thomas, Stephen R Clark, Sara A Mathie, Clare M Lloyd, Hartmut Kühn, Nicholas Topley, Barbara C Coles, Philip R Taylor, Simon A Jones, Valerie B O'Donnell. Phosphatidylethanolamine-esterified eicosanoids in the mouse: tissue localization and inflammation-dependent formation in Th-2 disease. The Journal of biological chemistry. 2009 Aug; 284(32):21185-91. doi: 10.1074/jbc.m109.021634. [PMID: 19531470]
  • Aaron T Wecksler, Cyril Jacquot, Wilfred A van der Donk, Theodore R Holman. Mechanistic investigations of human reticulocyte 15- and platelet 12-lipoxygenases with arachidonic acid. Biochemistry. 2009 Jul; 48(26):6259-67. doi: 10.1021/bi802332j. [PMID: 19469483]
  • Naonori Uozumi, Yoshihiro Kita, Takao Shimizu. Modulation of lipid and protein mediators of inflammation by cytosolic phospholipase A2alpha during experimental sepsis. Journal of immunology (Baltimore, Md. : 1950). 2008 Sep; 181(5):3558-66. doi: 10.4049/jimmunol.181.5.3558. [PMID: 18714029]
  • C-M Hao, M D Breyer. Physiologic and pathophysiologic roles of lipid mediators in the kidney. Kidney international. 2007 Jun; 71(11):1105-15. doi: 10.1038/sj.ki.5002192. [PMID: 17361113]
  • Chuan-Ming Hao, Matthew D Breyer. Roles of lipid mediators in kidney injury. Seminars in nephrology. 2007 May; 27(3):338-51. doi: 10.1016/j.semnephrol.2007.02.008. [PMID: 17533010]
  • Sarah Chouinard, Georges Pelletier, Alain Bélanger, Olivier Barbier. Isoform-specific regulation of uridine diphosphate-glucuronosyltransferase 2B enzymes in the human prostate: differential consequences for androgen and bioactive lipid inactivation. Endocrinology. 2006 Nov; 147(11):5431-42. doi: 10.1210/en.2006-0229. [PMID: 16887906]
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  • Petra Frohberg, Guntram Drutkowski, Ivonne Wobst. Monitoring eicosanoid biosynthesis via lipoxygenase and cyclooxygenase pathways in human whole blood by single HPLC run. Journal of pharmaceutical and biomedical analysis. 2006 Jun; 41(4):1317-24. doi: 10.1016/j.jpba.2006.02.046. [PMID: 16621414]
  • Joakim Huber, Alexander Fürnkranz, Valery N Bochkov, Mary K Patricia, Hans Lee, Catherine C Hedrick, Judith A Berliner, Bernd R Binder, Norbert Leitinger. Specific monocyte adhesion to endothelial cells induced by oxidized phospholipids involves activation of cPLA2 and lipoxygenase. Journal of lipid research. 2006 May; 47(5):1054-62. doi: 10.1194/jlr.m500555-jlr200. [PMID: 16461778]
  • S Sasson, J Eckel. Disparate effects of 12-lipoxygenase and 12-hydroxyeicosatetraenoic acid in vascular endothelial and smooth muscle cells and in cardiomyocytes. Archives of physiology and biochemistry. 2006 Apr; 112(2):119-29. doi: 10.1080/13813450600712035. [PMID: 16931454]
  • Shanqin Xu, Bingbing Jiang, Karlene A Maitland, Hossein Bayat, Jiali Gu, Jerry L Nadler, Stefano Corda, Gilbert Lavielle, Tony J Verbeuren, Adriana Zuccollo, Richard A Cohen. The thromboxane receptor antagonist S18886 attenuates renal oxidant stress and proteinuria in diabetic apolipoprotein E-deficient mice. Diabetes. 2006 Jan; 55(1):110-9. doi: 10.2337/diabetes.55.01.06.db05-0831. [PMID: 16380483]
  • Masako Matsuo. In vivo antioxidant activity of methanol extract from quinoa fermented with Rhizopus oligosporus. Journal of nutritional science and vitaminology. 2005 Dec; 51(6):449-52. doi: 10.3177/jnsv.51.449. [PMID: 16521706]
  • Haydee E P Bazan. Cellular and molecular events in corneal wound healing: significance of lipid signalling. Experimental eye research. 2005 Apr; 80(4):453-63. doi: 10.1016/j.exer.2004.12.023. [PMID: 15781273]
  • Uddhav P Kelavkar, Wayne Glasgow, Sandra J Olson, Barbara A Foster, Scott B Shappell. Overexpression of 12/15-lipoxygenase, an ortholog of human 15-lipoxygenase-1, in the prostate tumors of TRAMP mice. Neoplasia (New York, N.Y.). 2004 Nov; 6(6):821-30. doi: 10.1593/neo.04286. [PMID: 15720809]
  • Lei Sun, Shuju Feng, Julio C Reséndiz, Xin Lu, William Durante, Michael H Kroll. Role of the Pyk2-MAP kinase-cPLA2 signaling pathway in shear-dependent platelet aggregation. Annals of biomedical engineering. 2004 Sep; 32(9):1193-201. doi: 10.1114/b:abme.0000039353.97347.28. [PMID: 15493507]
  • Michiharu Tanabe, Sadaharu Tabuchi, Masato Iwatsuki, Masamichi Kurosaki, Hideki Kamitani, Masayuki Yokota, Takashi Watanabe. Incorporation of arachidonic and linoleic acid hydroperoxides into cultured human umbilical vein endothelial cells. Prostaglandins, leukotrienes, and essential fatty acids. 2004 Jun; 70(6):485-9. doi: 10.1016/j.plefa.2003.10.003. [PMID: 15120710]
  • Shih Shen Yiu, Xueying Zhao, Edward W Inscho, John D Imig. 12-Hydroxyeicosatetraenoic acid participates in angiotensin II afferent arteriolar vasoconstriction by activating L-type calcium channels. Journal of lipid research. 2003 Dec; 44(12):2391-9. doi: 10.1194/jlr.m300183-jlr200. [PMID: 12951362]
  • Naoto Suzuki, Takanori Hishinuma, Toshihide Saga, Jo Sato, Takayoshi Toyota, Junichi Goto, Michinao Mizugaki. Determination of urinary 12(S)-hydroxyeicosatetraenoic acid by liquid chromatography-tandem mass spectrometry with column-switching technique: sex difference in healthy volunteers and patients with diabetes mellitus. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Jan; 783(2):383-9. doi: 10.1016/s1570-0232(02)00666-9. [PMID: 12482481]
  • Ching-Jiunn Chen, Huei-Sheng Huang, Wen-Chang Chang. Inhibition of arachidonate metabolism in human epidermoid carcinoma a431 cells overexpressing phospholipid hydroperoxide glutathione peroxidase. Journal of biomedical science. 2002 Sep; 9(5):453-9. doi: 10.1007/bf02256540. [PMID: 12218361]
  • Xiao Han, Songyuan Chen, Yujie Sun, Jerry L Nadler, David Bleich. Induction of cyclooxygenase-2 gene in pancreatic beta-cells by 12-lipoxygenase pathway product 12-hydroxyeicosatetraenoic acid. Molecular endocrinology (Baltimore, Md.). 2002 Sep; 16(9):2145-54. doi: 10.1210/me.2001-0300. [PMID: 12198250]
  • Evgenia Alpert, Arie Gruzman, Hanan Totary, Nurit Kaiser, Reuven Reich, Shlomo Sasson. A natural protective mechanism against hyperglycaemia in vascular endothelial and smooth-muscle cells: role of glucose and 12-hydroxyeicosatetraenoic acid. The Biochemical journal. 2002 Mar; 362(Pt 2):413-22. doi: 10.1042/0264-6021:3620413. [PMID: 11853550]