Leukotriene A4 (BioDeep_00000004515)

 

Secondary id: BioDeep_00000629579

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraen-1-yl]oxiran-2-yl]butanoic acid

化学式: C20H30O3 (318.21948299999997)
中文名称:
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.06%

分子结构信息

SMILES: CCCCC/C=C\C/C=C\C=C\C=C\[C@H]1[C@H](CCCC(=O)O)O1
InChI: InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1

描述信息

Leukotriene A4 (LTA4) is the first metabolite in the series of reactions leading to the synthesis of all leukotrienes. 5-Lipoxygenase (5-LO) catalyzes the two-step conversion of arachidonic acid to LTA4.The first step consists of the oxidation of arachidonic acid to the unstable intermediate 5-hydroperoxyeicosatetraenoic acid (5-HPETE), and the second step is the dehydration of 5-HPETE to form LTA4. Leukotriene A4, an unstable epoxide, is hydrolyzed to leukotriene B4 or conjugated with glutathione to yield leukotriene C4 and its metabolites, leukotriene D4 and leukotriene E4. The leukotrienes participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. Recent studies also suggest a neuroendocrine role for leukotriene C4 in luteinizing hormone secretion. (PMID: 10591081, 2820055). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.
Leukotriene A4 (LTA4) is the first metabolite in the series of reactions leading to the synthesis of all leukotrienes. 5-Lipoxygenase (5-LO) catalyzes the two-step conversion of arachidonic acid to LTA4.The first step consists of the oxidation of arachidonic acid to the unstable intermediate 5-hydroperoxyeicosatetraenoic acid (5-HPETE), and the second step is the dehydration of 5-HPETE to form LTA4. Leukotriene A4, an unstable epoxide, is hydrolyzed to leukotriene B4 or conjugated with glutathione to yield leukotriene C4 and its metabolites, leukotriene D4 and leukotriene E4. The leukotrienes participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. Recent studies also suggest a neuroendocrine role for leukotriene C4 in luteinizing hormone secretion. (PMID: 10591081, 2820055)

同义名列表

22 个代谢物同义名

4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraen-1-yl]oxiran-2-yl]butanoic acid; (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoic acid; (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa- 7,9,11,14-tetraenoic acid; (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetrenoioc acid; (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acid; (5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acid; (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoate; (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa- 7,9,11,14-tetraenoate; (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoate; (5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoate; 5(S)-5,6-Oxido-7,9-trans-11,14-cis-eicosatetraenoic acid; 5(S)-5,6-Oxido-7,9-trans-11,14-cis-eicosatetraenoate; 5S,6S-epoxy-7E,9E,11Z,14Z-eicosatetraenoic acid; 5S,6S-Epoxy-7E,9E,11Z,14Z-eicosatetraenoate; 5,6-epoxy-7,9,11,14-eicosatetraenoic acid; 5S,6S-Leukotriene a4; Leukotriene a-4; Leukotriene a 4; Leukotriene A4; Leukotrienes a; Leukotriene a; LTA4



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

169 个相关的代谢反应过程信息。

Reactome(112)

BioCyc(0)

WikiPathways(10)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(46)

PharmGKB(0)

3 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

  • Tarvi Teder, Stefanie König, Rajkumar Singh, Bengt Samuelsson, Oliver Werz, Ulrike Garscha, Jesper Z Haeggström. Modulation of the 5-Lipoxygenase Pathway by Chalcogen-Containing Inhibitors of Leukotriene A4 Hydrolase. International journal of molecular sciences. 2023 Apr; 24(8):. doi: 10.3390/ijms24087539. [PMID: 37108702]
  • Zi-Jun Chen, Xiao-Qian Huo, Yue Ren, Zhan Shu, Yan-Ling Zhang. [Anti-osteoarthritis components and mechanism of Fufang Duzhong Jiangu Granules]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Aug; 47(15):4156-4163. doi: 10.19540/j.cnki.cjcmm.20220210.401. [PMID: 36046906]
  • Mingqian Fang, Xiaopeng Tang, Juan Zhang, Zhiyi Liao, Gan Wang, Ruomei Cheng, Zhiye Zhang, Hongwen Zhao, Jing Wang, Zhaoxia Tan, Peter Muiruri Kamau, Qiumin Lu, Qi Liu, Guohong Deng, Ren Lai. An inhibitor of leukotriene-A4 hydrolase from bat salivary glands facilitates virus infection. Proceedings of the National Academy of Sciences of the United States of America. 2022 03; 119(10):e2110647119. doi: 10.1073/pnas.2110647119. [PMID: 35238649]
  • Su Jing Chan, Mary P E Ng, Hui Zhao, Geelyn J L Ng, Chuan De Foo, Peter T-H Wong, Raymond C S Seet. Early and Sustained Increases in Leukotriene B4 Levels Are Associated with Poor Clinical Outcome in Ischemic Stroke Patients. Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics. 2020 01; 17(1):282-293. doi: 10.1007/s13311-019-00787-4. [PMID: 31520306]
  • Jia-Xiang Chen, Kun-Yue Xue, Juan-Juan Xin, Xin Yan, Ru-Li Li, Xiao-Xiao Wang, Xu-Lei Wang, Ming-Ming Tong, Lu Gan, He Li, Jie Lan, Xue Li, Cai-Li Zhuo, Ling-Yu Li, Zi-Jie Deng, Heng-Yu Zhang, Wei Jiang. 5-Lipoxagenase deficiency attenuates L-NAME-induced hypertension and vascular remodeling. Biochimica et biophysica acta. Molecular basis of disease. 2019 09; 1865(9):2379-2392. doi: 10.1016/j.bbadis.2019.05.021. [PMID: 31167124]
  • Erin E Schexnaydre, Jana Gerstmeier, Ulrike Garscha, Paul M Jordan, Oliver Werz, Marcia E Newcomer. A 5‑lipoxygenase-specific sequence motif impedes enzyme activity and confers dependence on a partner protein. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2019 04; 1864(4):543-551. doi: 10.1016/j.bbalip.2018.09.011. [PMID: 30291962]
  • Justin T English, Paul C Norris, Robin R Hodges, Darlene A Dartt, Charles N Serhan. Identification and Profiling of Specialized Pro-Resolving Mediators in Human Tears by Lipid Mediator Metabolomics. Prostaglandins, leukotrienes, and essential fatty acids. 2017 02; 117(?):17-27. doi: 10.1016/j.plefa.2017.01.004. [PMID: 28237084]
  • Shabbir Ahmad, A Jimmy Ytterberg, Madhuranayaki Thulasingam, Fredrik Tholander, Tomas Bergman, Roman Zubarev, Anders Wetterholm, Agnes Rinaldo-Matthis, Jesper Z Haeggström. Phosphorylation of Leukotriene C4 Synthase at Serine 36 Impairs Catalytic Activity. The Journal of biological chemistry. 2016 08; 291(35):18410-8. doi: 10.1074/jbc.m116.735647. [PMID: 27365393]
  • Valérie Capra, Chiara Carnini, Maria Rosa Accomazzo, Antonio Di Gennaro, Marco Fiumicelli, Emanuele Borroni, Ivan Brivio, Carola Buccellati, Paolo Mangano, Silvia Carnevali, Gianenrico Rovati, Angelo Sala. Autocrine activity of cysteinyl leukotrienes in human vascular endothelial cells: Signaling through the CysLT₂ receptor. Prostaglandins & other lipid mediators. 2015 Jul; 120(?):115-25. doi: 10.1016/j.prostaglandins.2015.03.007. [PMID: 25839425]
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  • Jing Jin, Yuxiang Zheng, William E Boeglin, Alan R Brash. Biosynthesis, isolation, and NMR analysis of leukotriene A epoxides: substrate chirality as a determinant of the cis or trans epoxide configuration. Journal of lipid research. 2013 Mar; 54(3):754-761. doi: 10.1194/jlr.m033746. [PMID: 23242647]
  • 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]
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  • Sundarapandian Thangapandian, Shalini John, Prettina Lazar, Sun Choi, Keun Woo Lee. Structural origins for the loss of catalytic activities of bifunctional human LTA4H revealed through molecular dynamics simulations. PloS one. 2012; 7(7):e41063. doi: 10.1371/journal.pone.0041063. [PMID: 22848428]
  • Sundarapandian Thangapandian, Shalini John, Sugunadevi Sakkiah, Keun Woo Lee. Molecular docking and pharmacophore filtering in the discovery of dual-inhibitors for human leukotriene A4 hydrolase and leukotriene C4 synthase. Journal of chemical information and modeling. 2011 Jan; 51(1):33-44. doi: 10.1021/ci1002813. [PMID: 21133343]
  • Dorothee Funk, Bernd L Sorg, Sabine C Lindner, Heinz H Schmeiser. 32P-postlabeling analysis of DNA adducts formed by leukotriene A4 (LTA4). Environmental and molecular mutagenesis. 2010 May; 51(4):338-43. doi: 10.1002/em.20547. [PMID: 20120015]
  • Angelo Sala, Giancarlo Folco, Robert C Murphy. Transcellular biosynthesis of eicosanoids. Pharmacological reports : PR. 2010 May; 62(3):503-10. doi: 10.1016/s1734-1140(10)70306-6. [PMID: 20631414]
  • Christopher L Rector, Robert C Murphy. Determination of leukotriene A(4) stabilization by S100A8/A9 proteins using mass spectrometry. Journal of lipid research. 2009 Oct; 50(10):2064-71. doi: 10.1194/jlr.m900017-jlr200. [PMID: 19269927]
  • Katrin Niisuke, William E Boeglin, John J Murray, Claus Schneider, Alan R Brash. Biosynthesis of a linoleic acid allylic epoxide: mechanistic comparison with its chemical synthesis and leukotriene A biosynthesis. Journal of lipid research. 2009 Jul; 50(7):1448-55. doi: 10.1194/jlr.m900025-jlr200. [PMID: 19244216]
  • V S Westergren, S J Wilson, J F Penrose, P H Howarth, A P Sampson. Nasal mucosal expression of the leukotriene and prostanoid pathways in seasonal and perennial allergic rhinitis. Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology. 2009 Jun; 39(6):820-8. doi: 10.1111/j.1365-2222.2009.03223.x. [PMID: 19364335]
  • Giancarlo Folco, Robert C Murphy. Eicosanoid transcellular biosynthesis: from cell-cell interactions to in vivo tissue responses. Pharmacological reviews. 2006 Sep; 58(3):375-88. doi: 10.1124/pr.58.3.8. [PMID: 16968946]
  • Marija Rakonjac, Lutz Fischer, Patrick Provost, Oliver Werz, Dieter Steinhilber, Bengt Samuelsson, Olof Rådmark. Coactosin-like protein supports 5-lipoxygenase enzyme activity and up-regulates leukotriene A4 production. Proceedings of the National Academy of Sciences of the United States of America. 2006 Aug; 103(35):13150-5. doi: 10.1073/pnas.0605150103. [PMID: 16924104]
  • Jennifer S Dickinson Zimmer, Douglas F Dyckes, David A Bernlohr, Robert C Murphy. Fatty acid binding proteins stabilize leukotriene A4: competition with arachidonic acid but not other lipoxygenase products. Journal of lipid research. 2004 Nov; 45(11):2138-44. doi: 10.1194/jlr.m400240-jlr200. [PMID: 15342681]
  • Joseph A Hankin, David N M Jones, Robert C Murphy. Covalent binding of leukotriene A4 to DNA and RNA. Chemical research in toxicology. 2003 Apr; 16(4):551-61. doi: 10.1021/tx034018+. [PMID: 12703973]
  • Marc E Surette, Iphigenia L Koumenis, Michelle B Edens, Kenneth M Tramposch, Bert Clayton, David Bowton, Floyd H Chilton. Inhibition of leukotriene biosynthesis by a novel dietary fatty acid formulation in patients with atopic asthma: a randomized, placebo-controlled, parallel-group, prospective trial. Clinical therapeutics. 2003 Mar; 25(3):972-9. doi: 10.1016/s0149-2918(03)80117-0. [PMID: 12852711]
  • Tankred Schewe, Hartmut Kühn, Helmut Sies. Flavonoids of cocoa inhibit recombinant human 5-lipoxygenase. The Journal of nutrition. 2002 Jul; 132(7):1825-9. doi: 10.1093/jn/132.7.1825. [PMID: 12097654]
  • James F Kachur, Leslie J Askonas, Doreen Villani-Price, Nayereh Ghoreishi-Haack, Suzanne Won-Kim, Chi-Dean D Liang, Mark A Russell, Walter G Smith. Pharmacological characterization of SC-57461A (3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl]amino]propanoic acid HCl), a potent and selective inhibitor of leukotriene A(4) hydrolase II: in vivo studies. The Journal of pharmacology and experimental therapeutics. 2002 Feb; 300(2):583-7. doi: 10.1124/jpet.300.2.583. [PMID: 11805220]
  • Iolanda M Fierro, Jeffery L Kutok, Charles N Serhan. Novel lipid mediator regulators of endothelial cell proliferation and migration: aspirin-triggered-15R-lipoxin A(4) and lipoxin A(4). The Journal of pharmacology and experimental therapeutics. 2002 Feb; 300(2):385-92. doi: 10.1124/jpet.300.2.385. [PMID: 11805195]
  • S Tornhamre, T J Schmidt, B Näsman-Glaser, I Ericsson, Lindgren JA. Inhibitory effects of helenalin and related compounds on 5-lipoxygenase and leukotriene C(4) synthase in human blood cells. Biochemical pharmacology. 2001 Oct; 62(7):903-11. doi: 10.1016/s0006-2952(01)00729-8. [PMID: 11543725]
  • M M Thunnissen, P Nordlund, J Z Haeggström. Crystal structure of human leukotriene A(4) hydrolase, a bifunctional enzyme in inflammation. Nature structural biology. 2001 Feb; 8(2):131-5. doi: 10.1038/84117. [PMID: 11175901]
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