15(S)-HPETE (BioDeep_00000006021)

 

Secondary id: BioDeep_00000629620, BioDeep_00000873132

human metabolite Endogenous blood metabolite natural product


代谢物信息卡片


15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer

化学式: C20H32O4 (336.2300472)
中文名称: 15-羟基二十碳-5Z,8Z,11Z,13E-四烯酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.06%

分子结构信息

SMILES: C(CC/C=C\C/C=C\C/C=C\C=C\[C@H](CCCCC)OO)C(=O)O
InChI: InChI=1S/C20H32O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h4-5,8-11,14,17,19,23H,2-3,6-7,12-13,15-16,18H2,1H3,(H,21,22)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1

描述信息

15(S)-hydroperoxyeicosatetraenoic acid (15(S)-HPETE) is the corresponding hydroperoxide of 15(S)-HETE and undergoes homolytic decomposition to the DNA-reactive bifunctional electrophile 4-oxo-2(E)-nonenal, a precursor of heptanone-etheno-2-deoxyguanosine. Reactive oxygen species convert the omega-6 polyunsaturated fatty acid arachidonic acid into (15-HPETE); vitamin C mediates 15(S)-HPETE decomposition. 15(S)-HPETE initiates apoptosis in vascular smooth muscle cells. 15(S)-HPETE is a lipoxygenase metabolite that affects the expression of cell adhesion molecules (CAMs) involved in the adhesion of leukocytes and/or the accumulation of leukocytes in the vascular endothelium, these being the initial events in endothelial cell injury. 15(S)-HPETE induces a loss of cardiomyocytes membrane integrity. 15-(S)HPETE is a hydroperoxide that enhances the activity of the enzymes lipoxygenase [EC 1.13.11.12] and Na+, K+-ATPase [EC 3.6.3.9] of brain microvessels. Lipoxygenase(s) and Na+-K+-ATPase of brain microvessels may play a significant role in the occurrence of ischemic brain edema. (PMID: 15964853, 15723435, 8655602, 8595608, 2662983).
D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents
D004791 - Enzyme Inhibitors > D016859 - Lipoxygenase Inhibitors
D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides

同义名列表

25 个代谢物同义名

15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer; (5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid; (5Z,8Z,11Z,13E,15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid; 15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (Z,Z,Z,Z)-isomer; 15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (e,Z,Z,Z)-isomer; (5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoate; (5Z,8Z,11Z,13E,15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoate; 15S-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid; 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid; 15-Hydroperoxy-5,8,11,14-eicosatetraenoic acid; 15-hydroperoxyicosa-5,8,11,13-tetraenoic acid; 15S-Hydroperoxyeicosatetraenoic acid; 15-Hydroperoxyeicosatetraenoic acid; 15-Hydroperoxyicosatetraenoic acid; Arachidonic acid 15-hydroperoxide; 15S-Hydroperoxyeicosatetraenoate; 15-Hydroperoxyeicosatetraenoate; 15-Hydroperoxyicosatetraenoate; 15-Hydroperoxyarachidonic acid; 14,15-Epoxyarachidonic acid; 15(S)-HPETE; 15S-HpETE; 15-HpETE; 15-HPAA; 15-HPEA



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(0)

PlantCyc(0)

代谢反应

138 个相关的代谢反应过程信息。

Reactome(89)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(46)

PharmGKB(0)

17 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

  • Haider H Dar, Michael W Epperly, Vladimir A Tyurin, Andrew A Amoscato, Tamil S Anthonymuthu, Austin B Souryavong, Alexander A Kapralov, Galina V Shurin, Svetlana N Samovich, Claudette M St Croix, Simon C Watkins, Sally E Wenzel, Rama K Mallampalli, Joel S Greenberger, Hülya Bayır, Valerian E Kagan, Yulia Y Tyurina. P. aeruginosa augments irradiation injury via 15-lipoxygenase-catalyzed generation of 15-HpETE-PE and induction of theft-ferroptosis. JCI insight. 2022 02; 7(4):. doi: 10.1172/jci.insight.156013. [PMID: 35041620]
  • Wan-Yang Sun, Vladimir A Tyurin, Karolina Mikulska-Ruminska, Indira H Shrivastava, Tamil S Anthonymuthu, Yu-Jia Zhai, Ming-Hai Pan, Hai-Biao Gong, Dan-Hua Lu, Jie Sun, Wen-Jun Duan, Sergey Korolev, Andrey Y Abramov, Plamena R Angelova, Ian Miller, Ofer Beharier, Gao-Wei Mao, Haider H Dar, Alexandr A Kapralov, Andrew A Amoscato, Teresa G Hastings, Timothy J Greenamyre, Charleen T Chu, Yoel Sadovsky, Ivet Bahar, Hülya Bayır, Yulia Y Tyurina, Rong-Rong He, Valerian E Kagan. Phospholipase iPLA2β averts ferroptosis by eliminating a redox lipid death signal. Nature chemical biology. 2021 04; 17(4):465-476. doi: 10.1038/s41589-020-00734-x. [PMID: 33542532]
  • Alexandr A Kapralov, Qin Yang, Haider H Dar, Yulia Y Tyurina, Tamil S Anthonymuthu, Rina Kim, Claudette M St Croix, Karolina Mikulska-Ruminska, Bing Liu, Indira H Shrivastava, Vladimir A Tyurin, Hsiu-Chi Ting, Yijen L Wu, Yuan Gao, Galina V Shurin, Margarita A Artyukhova, Liubov A Ponomareva, Peter S Timashev, Rosario M Domingues, Detcho A Stoyanovsky, Joel S Greenberger, Rama K Mallampalli, Ivet Bahar, Dmitry I Gabrilovich, Hülya Bayır, Valerian E Kagan. Redox lipid reprogramming commands susceptibility of macrophages and microglia to ferroptotic death. Nature chemical biology. 2020 03; 16(3):278-290. doi: 10.1038/s41589-019-0462-8. [PMID: 32080625]
  • Christopher Wolff, Christian Zoschke, Suresh Kumar Kalangi, Pallu Reddanna, Monika Schäfer-Korting. Tumor microenvironment determines drug efficacy in vitro - apoptotic and anti-inflammatory effects of 15-lipoxygenase metabolite, 13-HpOTrE. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2019 Sep; 142(?):1-7. doi: 10.1016/j.ejpb.2019.06.003. [PMID: 31176725]
  • Ying Zhang, Jiyoung Park, Seong-Jeong Han, Yongwoon Lim, Iha Park, Jong-Suk Kim, Hyun Ae Woo, Seung-Rock Lee. Peroxiredoxin III Protects Tumor Suppressor PTEN from Oxidation by 15-Hydroperoxy-eicosatetraenoic Acid. Oxidative medicine and cellular longevity. 2019; 2019(?):2828493. doi: 10.1155/2019/2828493. [PMID: 31636803]
  • Kristin D Droege, Mary E Keithly, Charles R Sanders, Richard N Armstrong, Matthew K Thompson. Structural Dynamics of 15-Lipoxygenase-2 via Hydrogen-Deuterium Exchange. Biochemistry. 2017 09; 56(38):5065-5074. doi: 10.1021/acs.biochem.7b00559. [PMID: 28809482]
  • Josefin Zschaler, Juergen Arnhold. The hydroperoxide moiety of aliphatic lipid hydroperoxides is not affected by hypochlorous acid. Chemistry and physics of lipids. 2014 Dec; 184(?):42-51. doi: 10.1016/j.chemphyslip.2014.09.005. [PMID: 25260666]
  • Carolina Vijil, Cecilia Hermansson, Anders Jeppsson, Göran Bergström, Lillemor Mattsson Hultén. Arachidonate 15-lipoxygenase enzyme products increase platelet aggregation and thrombin generation. PloS one. 2014; 9(2):e88546. doi: 10.1371/journal.pone.0088546. [PMID: 24533104]
  • Sasikumar J Soumya, Sheela Binu, A Helen, K Anil Kumar, P Reddanna, Perumana R Sudhakaran. Effect of 15-lipoxygenase metabolites on angiogenesis: 15(S)-HPETE is angiostatic and 15(S)-HETE is angiogenic. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2012 Jul; 61(7):707-18. doi: 10.1007/s00011-012-0463-5. [PMID: 22450700]
  • Jonathan Bertin, Corinne Barat, Sylvie Méthot, Michel J Tremblay. Interactions between prostaglandins, leukotrienes and HIV-1: possible implications for the central nervous system. Retrovirology. 2012 Jan; 9(?):4. doi: 10.1186/1742-4690-9-4. [PMID: 22236409]
  • Colleen Rock, Philip J Moos. Selenoprotein P protects cells from lipid hydroperoxides generated by 15-LOX-1. Prostaglandins, leukotrienes, and essential fatty acids. 2010 Oct; 83(4-6):203-10. doi: 10.1016/j.plefa.2010.08.006. [PMID: 20826080]
  • Nguyen Dang Hung, Mee Ree Kim, Dai-Eun Sok. Anti-inflammatory action of arachidonoyl lysophosphatidylcholine or 15-hydroperoxy derivative in zymosan A-induced peritonitis. Prostaglandins & other lipid mediators. 2009 Dec; 90(3-4):105-11. doi: 10.1016/j.prostaglandins.2009.10.001. [PMID: 19819343]
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  • Kotha Anil Kumar, Kalle M Arunasree, Karnati R Roy, Nishanth P Reddy, Ankireddy Aparna, Gorla Venkateswara Reddy, Pallu Reddanna. Effects of (15S)-hydroperoxyeicosatetraenoic acid and (15S)-hydroxyeicosatetraenoic acid on the acute- lymphoblastic-leukaemia cell line Jurkat: activation of the Fas-mediated death pathway. Biotechnology and applied biochemistry. 2009 Feb; 52(Pt 2):121-33. doi: 10.1042/ba20070264. [PMID: 18494609]
  • Lorraine M Sordillo, Katie L Streicher, Isis K Mullarky, Jeffery C Gandy, Wendy Trigona, Chris M Corl. Selenium inhibits 15-hydroperoxyoctadecadienoic acid-induced intracellular adhesion molecule expression in aortic endothelial cells. Free radical biology & medicine. 2008 Jan; 44(1):34-43. doi: 10.1016/j.freeradbiomed.2007.09.002. [PMID: 18045545]
  • Oscar A Bizzozero, Savanna Reyes, Jennifer Ziegler, Suzanne Smerjac. Lipid peroxidation scavengers prevent the carbonylation of cytoskeletal brain proteins induced by glutathione depletion. Neurochemical research. 2007 Dec; 32(12):2114-22. doi: 10.1007/s11064-007-9377-y. [PMID: 17551832]
  • Suraneni V K Mahipal, Jagu Subhashini, Madhava C Reddy, Metukuri M Reddy, Kotha Anilkumar, Karnati R Roy, Gorla V Reddy, Pallu Reddanna. Effect of 15-lipoxygenase metabolites, 15-(S)-HPETE and 15-(S)-HETE on chronic myelogenous leukemia cell line K-562: reactive oxygen species (ROS) mediate caspase-dependent apoptosis. Biochemical pharmacology. 2007 Jul; 74(2):202-14. doi: 10.1016/j.bcp.2007.04.005. [PMID: 17517376]
  • Hui-Chun Yeh, Ah-Lim Tsai, Lee-Ho Wang. Reaction mechanisms of 15-hydroperoxyeicosatetraenoic acid catalyzed by human prostacyclin and thromboxane synthases. Archives of biochemistry and biophysics. 2007 May; 461(2):159-68. doi: 10.1016/j.abb.2007.03.012. [PMID: 17459323]
  • Gang Wu, Corina E Rogge, Jinn-Shyan Wang, Richard J Kulmacz, Graham Palmer, Ah-Lim Tsai. Oxyferryl heme and not tyrosyl radical is the likely culprit in prostaglandin H synthase-1 peroxidase inactivation. Biochemistry. 2007 Jan; 46(2):534-42. doi: 10.1021/bi061859h. [PMID: 17209563]
  • Wendy L Trigona, Isis K Mullarky, Yuzhang Cao, Lorraine M Sordillo. Thioredoxin reductase regulates the induction of haem oxygenase-1 expression in aortic endothelial cells. The Biochemical journal. 2006 Feb; 394(Pt 1):207-16. doi: 10.1042/bj20050712. [PMID: 16209660]
  • Gianguido Coffa, Ann N Imber, Brendan C Maguire, Gurunathan Laxmikanthan, Claus Schneider, Betty J Gaffney, Alan R Brash. On the relationships of substrate orientation, hydrogen abstraction, and product stereochemistry in single and double dioxygenations by soybean lipoxygenase-1 and its Ala542Gly mutant. The Journal of biological chemistry. 2005 Nov; 280(46):38756-66. doi: 10.1074/jbc.m504870200. [PMID: 16157595]
  • Lorraine M Sordillo, James A Weaver, Yu-Zhang Cao, Chris Corl, Matt J Sylte, Isis K Mullarky. Enhanced 15-HPETE production during oxidant stress induces apoptosis of endothelial cells. Prostaglandins & other lipid mediators. 2005 May; 76(1-4):19-34. doi: 10.1016/j.prostaglandins.2004.10.007. [PMID: 15967159]
  • Judith V Ferrante, Antonio Ferrante. Novel role of lipoxygenases in the inflammatory response: promotion of TNF mRNA decay by 15-hydroperoxyeicosatetraenoic acid in a monocytic cell line. Journal of immunology (Baltimore, Md. : 1950). 2005 Mar; 174(6):3169-72. doi: 10.4049/jimmunol.174.6.3169. [PMID: 15749845]
  • Stephen R Clark, Peter B Anning, Marcus J Coffey, Andrew G Roberts, Lawrence J Marnett, Valerie B O'Donnell. Depletion of iNOS-derived nitric oxide by prostaglandin H synthase-2 in inflammation-activated J774.2 macrophages through lipohydroperoxidase turnover. The Biochemical journal. 2005 Feb; 385(Pt 3):815-21. doi: 10.1042/bj20041353. [PMID: 15461587]
  • Huiyong Yin, Ned A Porter. New insights regarding the autoxidation of polyunsaturated fatty acids. Antioxidants & redox signaling. 2005 Jan; 7(1-2):170-84. doi: 10.1089/ars.2005.7.170. [PMID: 15650406]
  • Michelle V Williams, Seon Hwa Lee, Ian A Blair. Liquid chromatography/mass spectrometry analysis of bifunctional electrophiles and DNA adducts from vitamin C mediated decomposition of 15-hydroperoxyeicosatetraenoic acid. Rapid communications in mass spectrometry : RCM. 2005; 19(6):849-58. doi: 10.1002/rcm.1854. [PMID: 15723435]
  • Viola C Ruddat, Rakesh Mogul, Ilya Chorny, Cameron Chen, Noah Perrin, Stephanie Whitman, Victor Kenyon, Matthew P Jacobson, Claude F Bernasconi, Theodore R Holman. Tryptophan 500 and arginine 707 define product and substrate active site binding in soybean lipoxygenase-1. Biochemistry. 2004 Oct; 43(41):13063-71. doi: 10.1021/bi0489098. [PMID: 15476400]
  • Margaret K Yu, Philip J Moos, Pamela Cassidy, Mark Wade, F A Fitzpatrick. Conditional expression of 15-lipoxygenase-1 inhibits the selenoenzyme thioredoxin reductase: modulation of selenoproteins by lipoxygenase enzymes. The Journal of biological chemistry. 2004 Jul; 279(27):28028-35. doi: 10.1074/jbc.m313939200. [PMID: 15123685]
  • Tuan Trang, Benjamin McNaull, Remi Quirion, Khem Jhamandas. Involvement of spinal lipoxygenase metabolites in hyperalgesia and opioid tolerance. European journal of pharmacology. 2004 Apr; 491(1):21-30. doi: 10.1016/j.ejphar.2004.03.022. [PMID: 15102529]
  • Masahiro Yoshinaga, F Gregory Buchanan, Raymond N DuBois. 15-LOX-1 inhibits p21 (Cip/WAF 1) expression by enhancing MEK-ERK 1/2 signaling in colon carcinoma cells. Prostaglandins & other lipid mediators. 2004 Jan; 73(1-2):111-22. doi: 10.1016/j.prostaglandins.2004.01.001. [PMID: 15165036]
  • Sandra L Pfister, Nancy Spitzbarth, Darryl C Zeldin, Pierre Lafite, Daniel Mansuy, William B Campbell. Rabbit aorta converts 15-HPETE to trihydroxyeicosatrienoic acids: potential role of cytochrome P450. Archives of biochemistry and biophysics. 2003 Dec; 420(1):142-52. doi: 10.1016/j.abb.2003.09.026. [PMID: 14622984]
  • Barbara Cavalieri, Maria-Giulia Perrelli, Manuela Aragno, Pierluigi Ramadori, Giuseppe Poli, Juan C Cutrìn. Ischaemic preconditioning modulates the activity of Kupffer cells during in vivo reperfusion injury of rat liver. Cell biochemistry and function. 2003 Dec; 21(4):299-305. doi: 10.1002/cbf.1028. [PMID: 14624466]
  • Nahid Moghaddami, Maurizio Costabile, Phulwinder K Grover, Hubertus P A Jersmann, Zhi H Huang, Charles S T Hii, Antonio Ferrante. Unique effect of arachidonic acid on human neutrophil TNF receptor expression: up-regulation involving protein kinase C, extracellular signal-regulated kinase, and phospholipase A2. Journal of immunology (Baltimore, Md. : 1950). 2003 Sep; 171(5):2616-24. doi: 10.4049/jimmunol.171.5.2616. [PMID: 12928414]
  • María A Balboa, Rebeca Pérez, Jesús Balsinde. Amplification mechanisms of inflammation: paracrine stimulation of arachidonic acid mobilization by secreted phospholipase A2 is regulated by cytosolic phospholipase A2-derived hydroperoxyeicosatetraenoic acid. Journal of immunology (Baltimore, Md. : 1950). 2003 Jul; 171(2):989-94. doi: 10.4049/jimmunol.171.2.989. [PMID: 12847271]
  • Paola Manini, Alessandra Napolitano, Emanuela Camera, Teresa Caserta, Mauro Picardo, Anna Palumbo, Marco d'Ischia. Ni2+ enhances Fe2+/peroxide-induced oxidation of arachidonic acid and formation of geno/cytotoxic 4-hydroxynonenal: a possible contributory mechanism in nickel toxicity and allergenicity. Biochimica et biophysica acta. 2003 Apr; 1621(1):9-16. doi: 10.1016/s0304-4165(03)00010-2. [PMID: 12667605]
  • Laura M S Baker, Leslie B Poole. Catalytic mechanism of thiol peroxidase from Escherichia coli. Sulfenic acid formation and overoxidation of essential CYS61. The Journal of biological chemistry. 2003 Mar; 278(11):9203-11. doi: 10.1074/jbc.m209888200. [PMID: 12514184]
  • Rainer Wiesner, Hiroshi Suzuki, Matthias Walther, Shozo Yamamoto, Hartmut Kuhn. Suicidal inactivation of the rabbit 15-lipoxygenase by 15S-HpETE is paralleled by covalent modification of active site peptides. Free radical biology & medicine. 2003 Feb; 34(3):304-15. doi: 10.1016/s0891-5849(02)01244-3. [PMID: 12543246]
  • Shailaja Kalyankrishna, Jean-Hugues Parmentier, Kafait U Malik. Arachidonic acid-derived oxidation products initiate apoptosis in vascular smooth muscle cells. Prostaglandins & other lipid mediators. 2002 Sep; 70(1-2):13-29. doi: 10.1016/s0090-6980(02)00010-2. [PMID: 12428675]
  • Huiyong Yin, Christine M Havrilla, Jason D Morrow, Ned A Porter. Formation of isoprostane bicyclic endoperoxides from the autoxidation of cholesteryl arachidonate. Journal of the American Chemical Society. 2002 Jul; 124(26):7745-54. doi: 10.1021/ja0201092. [PMID: 12083928]
  • J A Weaver, J F Maddox, Y Z Cao, I K Mullarky, L M Sordillo. Increased 15-HPETE production decreases prostacyclin synthase activity during oxidant stress in aortic endothelial cells. Free radical biology & medicine. 2001 Feb; 30(3):299-308. doi: 10.1016/s0891-5849(00)00466-4. [PMID: 11165876]
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  • S W Hwang, H Cho, J Kwak, S Y Lee, C J Kang, J Jung, S Cho, K H Min, Y G Suh, D Kim, U Oh. Direct activation of capsaicin receptors by products of lipoxygenases: endogenous capsaicin-like substances. Proceedings of the National Academy of Sciences of the United States of America. 2000 May; 97(11):6155-60. doi: 10.1073/pnas.97.11.6155. [PMID: 10823958]
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