Leukotriene E4 (BioDeep_00000006013)

 

Secondary id: BioDeep_00000629573

human metabolite Endogenous blood metabolite


代谢物信息卡片


(5S-(5R*,6S*(s*),7E,9E,11Z,14Z))-6-((2-amino-2-carboxyethyl)thio)-5-hydroxy-7,9,11,14-eicosatetraenoic acid

化学式: C23H37NO5S (439.2392)
中文名称: 白三烯E4
谱图信息: 最多检出来源 Homo sapiens(blood) 37.72%

分子结构信息

SMILES: CCCCC/C=C\C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)SC[C@@H](C(=O)O)N
InChI: InChI=1S/C23H37NO5S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-21(30-18-19(24)23(28)29)20(25)15-14-17-22(26)27/h6-7,9-13,16,19-21,25H,2-5,8,14-15,17-18,24H2,1H3,(H,26,27)(H,28,29)/b7-6-,10-9-,12-11+,16-13+/t19-,20-,21+/m0/s1

描述信息

Leukotriene E4 (LTE4) is a cysteinyl leukotriene. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. Nasal blockage induced by CysLTs is mainly due to dilatation of nasal blood vessels, which can be induced by the nitric oxide produced through CysLT1 receptor activation. LTE4 activates contractile and inflammatory processes via specific interaction with putative seven transmembrane-spanning receptors that couple to G proteins and subsequent intracellular signaling pathways. LTE4 is metabolized from leukotriene C4 in a reaction catalyzed by gamma-glutamyl transpeptidase and a particulate dipeptidase from kidney (PMID: 12607939, 12432945, 6311078). 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 and are 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 signaling pathways.
Leukotriene E4 (LTE4) is a cysteinyl leukotriene. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. Nasal blockage induced by CysLTs is mainly due to dilatation of nasal blood vessels, which can be induced by the nitric oxide produced through CysLT1 receptor activation. LTE4, activate contractile and inflammatory processes via specific interaction with putative seven transmembrane-spanning receptors that couple to G proteins and subsequent intracellular signaling pathways. LTE4 is metabolized from leukotriene C4 in a reaction catalyzed by gamma-glutamyl transpeptidase and a particulate dipeptidase from kidney. (PMID: 12607939, 12432945, 6311078)

同义名列表

18 个代谢物同义名

(5S-(5R*,6S*(s*),7E,9E,11Z,14Z))-6-((2-amino-2-carboxyethyl)thio)-5-hydroxy-7,9,11,14-eicosatetraenoic acid; (5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid; (5S-(5R*,6S*(s*),7E,9E,11Z,14Z))-6-((2-amino-2-carboxyethyl)thio)-5-hydroxy-7,9,11,14-eicosatetraenoate; (7E,9E,11Z,14Z)-(5S,6R)-6-(Cystein-S-yl)-5-hydroxyeicosa-7,9,11,14-tetraenoic acid; (7E,9E,11Z,14Z)-(5S,6R)-6-(Cystein-S-yl)-5-hydroxyicosa-7,9,11,14-tetraenoic acid; (7E,9E,11Z,14Z)-(5S,6R)-6-(Cystein-S-yl)-5-hydroxyeicosa-7,9,11,14-tetraenoate; (7E,9E,11Z,14Z)-(5S,6R)-6-(Cystein-S-yl)-5-hydroxyicosa-7,9,11,14-tetraenoate; 5S-hydroxy-6R-(S-cysteinyl)-7E,9E,11Z,14Z-eicosatetraenoic acid; 5S-Hydroxy,6R-(S-cysteinyl),7E,9E,11Z,14Z-eicosatetraenoic acid; 5S-Hydroxy,6R-(S-cysteinyl),7E,9E,11Z,14Z-eicosatetraenoate; 11-trans Leukotriene E4; Leukotriene e 4; Leukotriene e-4; Leukotrienes e; Leukotriene E4; Leukotriene E; LTE4; Leukotriene E4



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(8)

BioCyc(0)

PlantCyc(0)

代谢反应

121 个相关的代谢反应过程信息。

Reactome(117)

BioCyc(0)

WikiPathways(4)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

2 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。

亚细胞结构定位 关联基因列表
Cytoplasm 4 ALOX5, IL13, PTGS1, PTGS2
Peripheral membrane protein 3 ALOX5, PTGS1, PTGS2
Endoplasmic reticulum membrane 3 LTC4S, PTGS1, PTGS2
Nucleus 2 LMNA, MPO
cytosol 2 ALOX5, LMNA
nucleoplasm 3 ALOX5, LMNA, MPO
Cell membrane 4 CYSLTR2, OXGR1, P2RY12, TNF
Cytoplasmic granule 1 RNASE2
Multi-pass membrane protein 4 CYSLTR2, LTC4S, OXGR1, P2RY12
cell surface 2 P2RY12, TNF
Golgi apparatus 1 PTGS1
neuronal cell body 1 TNF
Cytoplasm, cytosol 1 ALOX5
Lysosome 2 MPO, RNASE2
plasma membrane 7 CYSLTR1, CYSLTR2, IGHE, KNG1, OXGR1, P2RY12, TNF
Membrane 4 CYSLTR1, LTC4S, OXGR1, P2RY12
caveola 1 PTGS2
extracellular exosome 4 KNG1, MPO, PTGS1, RNASE2
endoplasmic reticulum 2 LTC4S, PTGS2
extracellular space 12 ALOX5, CXCL8, IGHE, IL13, IL4, IL5, IL6, KNG1, MPO, RNASE2, RNASE3, TNF
perinuclear region of cytoplasm 2 ALOX5, LMNA
protein-containing complex 1 PTGS2
intracellular membrane-bounded organelle 3 LTC4S, MPO, PTGS1
Microsome membrane 2 PTGS1, PTGS2
Single-pass type I membrane protein 1 IGHE
Secreted 5 CXCL8, IL13, IL4, IL5, IL6
extracellular region 12 ALOX5, CXCL8, IGHE, IL13, IL4, IL5, IL6, KNG1, MPO, RNASE2, RNASE3, TNF
photoreceptor outer segment 1 PTGS1
Nucleus membrane 2 ALOX5, LTC4S
nuclear membrane 3 ALOX5, LMNA, LTC4S
external side of plasma membrane 2 IL13, TNF
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cytoplasm, perinuclear region 1 ALOX5
Membrane raft 1 TNF
collagen-containing extracellular matrix 1 KNG1
secretory granule 1 MPO
intermediate filament 1 LMNA
nuclear speck 1 LMNA
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 2 LTC4S, PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 2 LTC4S, PTGS2
neuron projection 2 PTGS1, PTGS2
IgE immunoglobulin complex 1 IGHE
phagocytic cup 1 TNF
Secreted, extracellular space 1 KNG1
blood microparticle 1 KNG1
[Isoform 2]: Cell membrane 1 IGHE
site of double-strand break 1 LMNA
nuclear envelope 3 ALOX5, LMNA, LTC4S
Nucleus envelope 2 ALOX5, LMNA
Endomembrane system 1 PTGS1
Nucleus, nucleoplasm 1 LMNA
azurophil granule 1 MPO
ficolin-1-rich granule lumen 1 ALOX5
secretory granule lumen 1 ALOX5
endoplasmic reticulum lumen 3 IL6, KNG1, PTGS2
nuclear matrix 2 ALOX5, LMNA
platelet alpha granule lumen 1 KNG1
azurophil granule lumen 3 MPO, RNASE2, RNASE3
Nucleus matrix 2 ALOX5, LMNA
nuclear envelope lumen 1 ALOX5
nuclear lamina 1 LMNA
phagocytic vesicle lumen 1 MPO
[Isoform 3]: Cell membrane 1 IGHE
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
Nucleus lamina 1 LMNA
[Isoform C]: Nucleus speckle 1 LMNA
lamin filament 1 LMNA
interleukin-6 receptor complex 1 IL6
Nucleus intermembrane space 1 ALOX5
cell body membrane 1 P2RY12
cell projection membrane 1 P2RY12
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Katherine N Cahill, Pingsheng Wu, Ginger L Milne, Taneem Amin, Joseph Singer, Katherine Murphy, Erin Lewis, Deborah Gapko, Joshua A Boyce, Katherine M Buchheit, Tanya M Laidlaw. Mediator production and severity of aspirin-induced respiratory reactions: Impact of sampling site and body mass index. The Journal of allergy and clinical immunology. 2022 07; 150(1):170-177.e6. doi: 10.1016/j.jaci.2021.12.787. [PMID: 35026207]
  • Garret Choby, Christopher M Low, Joshua M Levy, Janalee K Stokken, Carlos Pinheiro-Neto, Kathy Bartemes, Michael Marino, Joseph K Han, Rohit Divekar, Erin K O'Brien, Devyani Lal. Urine Leukotriene E4: Implications as a Biomarker in Chronic Rhinosinusitis. Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery. 2022 02; 166(2):224-232. doi: 10.1177/01945998211011060. [PMID: 33973823]
  • Catherine R Weiler. How good are mast cell mediators?. Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology. 2021 10; 127(4):410-411. doi: 10.1016/j.anai.2021.07.016. [PMID: 34303837]
  • 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]
  • Garret Choby, Erin K O'Brien, Alyssa Smith, Jason Barnes, John Hagan, Janalee K Stokken, Andrew Strumpf, Jose L Mattos, Spencer C Payne, Rohit Divekar. Elevated Urine Leukotriene E4 Is Associated With Worse Objective Markers in Nasal Polyposis Patients. The Laryngoscope. 2021 05; 131(5):961-966. doi: 10.1002/lary.29137. [PMID: 33001452]
  • Johan Kolmert, Cristina Gómez, David Balgoma, Marcus Sjödin, Johan Bood, Jon R Konradsen, Magnus Ericsson, John-Olof Thörngren, Anna James, Maria Mikus, Ana R Sousa, John H Riley, Stewart Bates, Per S Bakke, Ioannis Pandis, Massimo Caruso, Pascal Chanez, Stephen J Fowler, Thomas Geiser, Peter Howarth, Ildikó Horváth, Norbert Krug, Paolo Montuschi, Marek Sanak, Annelie Behndig, Dominick E Shaw, Richard G Knowles, Cécile T J Holweg, Åsa M Wheelock, Barbro Dahlén, Björn Nordlund, Kjell Alving, Gunilla Hedlin, Kian Fan Chung, Ian M Adcock, Peter J Sterk, Ratko Djukanovic, Sven-Erik Dahlén, Craig E Wheelock. Urinary Leukotriene E4 and Prostaglandin D2 Metabolites Increase in Adult and Childhood Severe Asthma Characterized by Type 2 Inflammation. A Clinical Observational Study. American journal of respiratory and critical care medicine. 2021 01; 203(1):37-53. doi: 10.1164/rccm.201909-1869oc. [PMID: 32667261]
  • R Stokes Peebles. Urine: A Lens for Asthma Pathogenesis and Treatment?. American journal of respiratory and critical care medicine. 2021 01; 203(1):1-3. doi: 10.1164/rccm.202007-2899ed. [PMID: 32791002]
  • Youngwoo Choi, Soyoon Sim, Dong-Hyun Lee, Hee-Ra Lee, Ga-Young Ban, Yoo Seob Shin, Yoon-Keun Kim, Hae-Sim Park. Effect of TGF-β1 on eosinophils to induce cysteinyl leukotriene E4 production in aspirin-exacerbated respiratory disease. PloS one. 2021; 16(8):e0256237. doi: 10.1371/journal.pone.0256237. [PMID: 34437574]
  • Demet Yalçın Kehribar, Mustafa Cihangiroğlu, Emine Sehmen, Bahattin Avcı, Mustafa Çapraz, Maruf Boran, Caner Günaydin, Metin Özgen. The assessment of the serum levels of TWEAK and prostaglandin F2α in COVID – 19. Turkish journal of medical sciences. 2020 12; 50(8):1786-1791. doi: 10.3906/sag-2006-96. [PMID: 32979900]
  • Lars Löfgren, Gun-Britt Forsberg, Pia Davidsson, Susanna Eketjäll, Carl Whatling. Development of a highly sensitive liquid chromatography-mass spectrometry method to quantify plasma leukotriene E4 and demonstrate pharmacological suppression of endogenous 5-LO pathway activity in man. Prostaglandins & other lipid mediators. 2020 10; 150(?):106463. doi: 10.1016/j.prostaglandins.2020.106463. [PMID: 32450304]
  • Michele Biagioli, Adriana Carino, Silvia Marchianò, Rosalinda Roselli, Cristina Di Giorgio, Martina Bordoni, Chiara Fiorucci, Valentina Sepe, Paolo Conflitti, Vittorio Limongelli, Eleonora Distrutti, Monia Baldoni, Angela Zampella, Stefano Fiorucci. Identification of cysteinyl-leukotriene-receptor 1 antagonists as ligands for the bile acid receptor GPBAR1. Biochemical pharmacology. 2020 07; 177(?):113987. doi: 10.1016/j.bcp.2020.113987. [PMID: 32330496]
  • Alvaro Garcia-Cruz, Todd Cowen, Annelies Voorhaar, Elena Piletska, Sergey A Piletsky. Molecularly imprinted nanoparticles-based assay (MINA) - detection of leukotrienes and insulin. The Analyst. 2020 Jun; 145(12):4224-4232. doi: 10.1039/d0an00419g. [PMID: 32496501]
  • Hiroaki Hayashi, Yuma Fukutomi, Chihiro Mitsui, Keiichi Kajiwara, Kentaro Watai, Yosuke Kamide, Yuto Nakamura, Yuto Hamada, Yasuhiro Tomita, Kiyoshi Sekiya, Takahiro Tsuburai, Kenji Izuhara, Keiko Wakahara, Naozumi Hashimoto, Yoshinori Hasegawa, Masami Taniguchi. Omalizumab for Aspirin Hypersensitivity and Leukotriene Overproduction in Aspirin-exacerbated Respiratory Disease. A Randomized Controlled Trial. American journal of respiratory and critical care medicine. 2020 06; 201(12):1488-1498. doi: 10.1164/rccm.201906-1215oc. [PMID: 32142372]
  • Natalia Rivera, Carlos Flores, Maureen Morales, Oslando Padilla, Solange Causade, Pablo E Brockmann, Jose A Castro-Rodriguez. Preschoolers with recurrent wheezing have a high prevalence of sleep disordered breathing. The Journal of asthma : official journal of the Association for the Care of Asthma. 2020 06; 57(6):584-592. doi: 10.1080/02770903.2019.1599385. [PMID: 30950302]
  • Joseph H Butterfield. Survey of Mast Cell Mediator Levels from Patients Presenting with Symptoms of Mast Cell Activation. International archives of allergy and immunology. 2020; 181(1):43-50. doi: 10.1159/000503964. [PMID: 31722348]
  • Wande Benka-Coker, Christine Loftus, Catherine Karr, Sheryl Magzamen. Association of Organophosphate Pesticide Exposure and a Marker of Asthma Morbidity in an Agricultural Community. Journal of agromedicine. 2020 01; 25(1):106-114. doi: 10.1080/1059924x.2019.1619644. [PMID: 31130077]
  • Patrudu Makena, Gang Liu, Peter Chen, Charles R Yates, G L Prasad. Urinary Leukotriene E4 and 2,3-Dinor Thromboxane B2 Are Biomarkers of Potential Harm in Short-Term Tobacco Switching Studies. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2019 Dec; 28(12):2095-2105. doi: 10.1158/1055-9965.epi-19-0342. [PMID: 31558507]
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  • Inmaculada Doña, Raquel Jurado-Escobar, James R Perkins, Pedro Ayuso, María Carmen Plaza-Serón, Natalia Pérez-Sánchez, Paloma Campo, Gador Bogas-Herrera, Joan Bartra, María José Torres, Marek Sanak, José Antonio Cornejo-García. Eicosanoid mediator profiles in different phenotypes of nonsteroidal anti-inflammatory drug-induced urticaria. Allergy. 2019 06; 74(6):1135-1144. doi: 10.1111/all.13725. [PMID: 30667070]
  • Lucyna Mastalerz, Katarzyna E Tyrak, Maria Ignacak, Ewa Konduracka, Filip Mejza, Adam Ćmiel, Michał Buczek, Adrianna Kot, Krzysztof Oleś, Marek Sanak. Prostaglandin E2 decrease in induced sputum of hypersensitive asthmatics during oral challenge with aspirin. Allergy. 2019 05; 74(5):922-932. doi: 10.1111/all.13671. [PMID: 30446997]
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  • Grazyna Bochenek, Tomasz Stachura, Krystyna Szafraniec, Hanna Plutecka, Marek Sanak, Ewa Nizankowska-Mogilnicka, Krzysztof Sladek. Diagnostic Accuracy of Urinary LTE4 Measurement to Predict Aspirin-Exacerbated Respiratory Disease in Patients with Asthma. The journal of allergy and clinical immunology. In practice. 2018 Mar; 6(2):528-535. doi: 10.1016/j.jaip.2017.07.001. [PMID: 28888846]
  • Edyta Stodółkiewicz, Barbara Rewerska, Marcin Rzeszutko, Marek Tomala, Anton Chrustowicz, Krzysztof Żmudka, Marek Sanak, Wojciech Szczeklik. Leukotriene biosynthesis in coronary artery disease. Results of the Leukotrienes and Thromboxane In Myocardial Infarction (LTIMI) study. Polish archives of internal medicine. 2018 01; 128(1):43-51. doi: 10.20452/pamw.4140. [PMID: 29112183]
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