Leukotriene D4 (BioDeep_00000003315)

 

Secondary id: BioDeep_00000629574

human metabolite Endogenous blood metabolite


代谢物信息卡片


(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid

化学式: C25H40N2O6S (496.2607)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 35.36%

分子结构信息

SMILES: CCCCCC=CCC=CC=CC=CC(C(CCCC(=O)O)O)SCC(C(=O)NCC(=O)O)N
InChI: InChI=1S/C25H40N2O6S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22(21(28)15-14-17-23(29)30)34-19-20(26)25(33)27-18-24(31)32/h6-7,9-13,16,20-22,28H,2-5,8,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b7-6-,10-9-,12-11+,16-13+/t20-,21-,22+/m0/s1

描述信息

Leukotriene D4 (LTD4) 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. LTD4 is a pro-inflammatory mediator known to mediate its effects through specific cell-surface receptors belonging to the G-protein-coupled receptor family, namely the high-affinity CysLT1 (cysteinyl leukotriene 1) receptor. LTD4 is present at high levels in many inflammatory conditions, and areas of chronic inflammation have an increased risk for subsequent cancer development. LTD4 is associated with the pathogenesis of several inflammatory disorders, such as asthma and inflammatory bowel disease. Exposure to LTD4 increases survival and proliferation in intestinal epithelial cells. CysLT1 regulator is up-regulated in colon cancer tissue and LTD4 signalling facilitates the survival of cancer cells. LTD4 could reduce apoptosis in non-transformed epithelial cells. LTD4 causes up-regulation of beta-catenin through the CysLT1 receptor, PI3K (phosphoinositide 3-kinase), and GSK-3β (glycogen synthase kinase 3β). LTD4 induces beta-catenin translocation to the nucleus and activation of TCF/LEF family of transcription factors. LTD4 causes accumulation of free beta-catenin in non-transformed intestinal epithelial cells through the CysLT1 receptor, and this accumulation is dependent upon the activation of PI3K as well as GSK-3β inactivation (PMID: 16042577, 12607939). 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 D4 (LTD4) is a cysteinyl leukotriene a family of potent inflammatory mediators. LTD4 is a pro-inflammatory mediator known to mediate its effects through specific cell-surface receptors belonging to the G-protein-coupled receptor family, namely the high-affinity CysLT1 (cysteinyl leukotriene 1) receptor. LTD4 is present at high levels in many inflammatory conditions, and areas of chronic inflammation have an increased risk for subsequent cancer development; LTD4 is associated with the pathogenesis of several inflammatory disorders, such as asthma and inflammatory bowel disease. Exposure to LTD4 increases survival and proliferation in intestinal epithelial cells. CysLT1 regulator is up-regulated in colon cancer tissue and LTD4 signalling facilitates the survival of cancer cells. LTD4 could reduce apoptosis in non-transformed epithelial cells. LTD4 causes up-regulation of b-catenin through the CysLT1 receptor, PI3K (phosphoinositide 3-kinase) and GSK-3b (glycogen synthase kinase 3b). LTD4 induces b-catenin translocation to the nucleus and activation of TCF/LEF family of transcription factors. LTD4 causes accumulation of free b-catenin in non-transformed intestinal epithelial cells through the CysLT1 receptor, and this accumulation is dependent upon the activation of PI3K as well as GSK-3b inactivation. (PMID: 16042577, 12607939)

同义名列表

12 个代谢物同义名

(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid; (R-(R*,s*-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-L-cysteinyl)glycine; 5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid; 5S-Hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoate; Leukotriene D 4; Leukotriene D-4; Leukotrienes D; Leukotriene D4; Leukotriene D; FT-0641731; LTD4; Leukotriene D4



数据库引用编号

20 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

200 个相关的代谢反应过程信息。

Reactome(149)

BioCyc(0)

WikiPathways(4)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(46)

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。

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亚细胞结构定位 关联基因列表
Cytoplasm 6 ALOX5, CTNNB1, ITPR3, MAPK14, MME, PIK3C3
Peripheral membrane protein 1 ALOX5
Endoplasmic reticulum membrane 1 ITPR3
Cytoplasmic vesicle, autophagosome 1 PIK3C3
Nucleus 4 CTNNB1, FOSB, LMNA, MAPK14
autophagosome 1 PIK3C3
cytosol 7 ALOX5, CTNNB1, FOSB, LMNA, MAPK14, PIK3C3, PRKCQ
dendrite 1 MME
phosphatidylinositol 3-kinase complex, class III 1 PIK3C3
trans-Golgi network 1 MME
centrosome 1 CTNNB1
nucleoplasm 6 ALOX5, CTNNB1, FOSB, ITPR3, LMNA, MAPK14
Cell membrane 5 CTNNB1, CYSLTR2, GPRC5A, MME, TNF
lamellipodium 1 CTNNB1
Multi-pass membrane protein 3 CYSLTR2, GPRC5A, ITPR3
Synapse 2 CTNNB1, MME
cell cortex 1 CTNNB1
cell junction 1 CTNNB1
cell surface 2 MME, TNF
glutamatergic synapse 3 CTNNB1, MAPK14, PIK3C3
lysosomal membrane 1 EGF
neuronal cell body 3 ITPR3, MME, TNF
presynaptic membrane 1 CTNNB1
synaptic vesicle 1 MME
Cytoplasm, cytosol 1 ALOX5
Presynapse 1 MME
endosome 1 PIK3C3
plasma membrane 11 CTNNB1, CYSLTR1, CYSLTR2, EGF, GPRC5A, IGHE, ITPR3, KNG1, MME, PRKCQ, TNF
Membrane 6 CTNNB1, CYSLTR1, EGF, ITPR3, MME, PIK3C3
axon 1 MME
basolateral plasma membrane 1 CTNNB1
brush border 2 ITPR3, MME
extracellular exosome 5 CTNNB1, EGF, GPRC5A, KNG1, MME
endoplasmic reticulum 1 ITPR3
extracellular space 8 ALOX5, CXCL8, EGF, IGHE, IL4, IL5, KNG1, TNF
perinuclear region of cytoplasm 3 ALOX5, CTNNB1, LMNA
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 1 CTNNB1
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
mitochondrion 1 MAPK14
protein-containing complex 1 CTNNB1
intracellular membrane-bounded organelle 2 FOSB, GPRC5A
Single-pass type I membrane protein 1 IGHE
Secreted 4 CXCL8, IL4, IL5, TRH
extracellular region 10 ALOX5, CXCL8, EGF, IGHE, IL4, IL5, KNG1, MAPK14, TNF, TRH
transcription regulator complex 1 CTNNB1
centriolar satellite 1 PRKCQ
Nucleus membrane 1 ALOX5
nuclear membrane 2 ALOX5, LMNA
external side of plasma membrane 1 TNF
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
cytoplasmic vesicle 1 MME
nucleolus 2 GPRC5A, ITPR3
Wnt signalosome 1 CTNNB1
midbody 1 PIK3C3
Early endosome 1 MME
apical part of cell 2 CTNNB1, ITPR3
cell-cell junction 1 CTNNB1
recycling endosome 1 TNF
Single-pass type II membrane protein 2 MME, TNF
vesicle 1 GPRC5A
postsynaptic membrane 1 CTNNB1
Cytoplasm, perinuclear region 1 ALOX5
Membrane raft 2 MME, TNF
Cytoplasm, cytoskeleton 1 CTNNB1
focal adhesion 2 CTNNB1, MME
GABA-ergic synapse 1 PIK3C3
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
Peroxisome 1 PIK3C3
sarcoplasmic reticulum 1 ITPR3
collagen-containing extracellular matrix 1 KNG1
secretory granule 1 TRH
fascia adherens 1 CTNNB1
intermediate filament 1 LMNA
lateral plasma membrane 1 CTNNB1
axoneme 1 PIK3C3
nuclear speck 2 LMNA, MAPK14
nuclear outer membrane 1 ITPR3
Late endosome 1 PIK3C3
receptor complex 2 GPRC5A, ITPR3
chromatin 1 FOSB
IgE immunoglobulin complex 1 IGHE
phagocytic cup 1 TNF
phagocytic vesicle membrane 1 PIK3C3
cell periphery 1 CTNNB1
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
Secreted, extracellular space 1 KNG1
spindle pole 2 CTNNB1, MAPK14
blood microparticle 1 KNG1
postsynaptic density, intracellular component 1 CTNNB1
microvillus membrane 1 CTNNB1
[Isoform 2]: Cell membrane 1 IGHE
site of double-strand break 1 LMNA
nuclear envelope 2 ALOX5, LMNA
Nucleus envelope 2 ALOX5, LMNA
Endomembrane system 1 CTNNB1
phagophore assembly site 1 PIK3C3
phosphatidylinositol 3-kinase complex, class III, type I 1 PIK3C3
phosphatidylinositol 3-kinase complex, class III, type II 1 PIK3C3
Cytoplasmic vesicle membrane 1 GPRC5A
Nucleus, nucleoplasm 1 LMNA
euchromatin 1 CTNNB1
ficolin-1-rich granule lumen 2 ALOX5, MAPK14
secretory granule lumen 2 ALOX5, MAPK14
secretory granule membrane 2 ITPR3, MME
endoplasmic reticulum lumen 1 KNG1
nuclear matrix 2 ALOX5, LMNA
platelet alpha granule lumen 2 EGF, KNG1
beta-catenin-TCF complex 1 CTNNB1
immunological synapse 1 PRKCQ
presynaptic endosome 1 PIK3C3
aggresome 1 PRKCQ
Nucleus matrix 2 ALOX5, LMNA
nuclear envelope lumen 1 ALOX5
presynaptic active zone cytoplasmic component 1 CTNNB1
nuclear lamina 1 LMNA
clathrin-coated endocytic vesicle membrane 1 EGF
platelet dense tubular network membrane 1 ITPR3
protein-DNA complex 1 CTNNB1
Cytoplasmic vesicle, secretory vesicle membrane 1 ITPR3
catenin complex 1 CTNNB1
[Isoform 3]: Cell membrane 1 IGHE
postsynaptic endosome 1 PIK3C3
[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
transport vesicle membrane 1 ITPR3
Nucleus lamina 1 LMNA
[Isoform C]: Nucleus speckle 1 LMNA
lamin filament 1 LMNA
Autolysosome 1 PIK3C3
neuron projection terminus 1 MME
Nucleus intermembrane space 1 ALOX5
beta-catenin-TCF7L2 complex 1 CTNNB1
cytoplasmic side of endoplasmic reticulum membrane 1 ITPR3
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Jesper Säfholm, Willem Abma, Lora G Bankova, Joshua A Boyce, Mamdoh Al-Ameri, Ann-Charlotte Orre, Craig E Wheelock, Sven-Erik Dahlén, Mikael Adner. Cysteinyl-maresin 3 inhibits IL-13 induced airway hyperresponsiveness through alternative activation of the CysLT1 receptor. European journal of pharmacology. 2022 Nov; 934(?):175257. doi: 10.1016/j.ejphar.2022.175257. [PMID: 36116518]
  • Ko Fujimori, Saki Uno, Kyohei Kuroda, Chihiro Matsumoto, Toko Maehara. Leukotriene C4 synthase is a novel PPARγ target gene, and leukotriene C4 and D4 activate adipogenesis through cysteinyl LT1 receptors in adipocytes. Biochimica et biophysica acta. Molecular cell research. 2022 03; 1869(3):119203. doi: 10.1016/j.bbamcr.2021.119203. [PMID: 34968576]
  • Hirofumi Fujita, Aoi Ando, Yohei Mizusawa, Mitsuaki Ono, Takako Hattori, Munenori Habuta, Toshitaka Oohashi, Satoshi Kubota, Hideyo Ohuchi. Cysteinyl leukotriene receptor 1 is dispensable for osteoclast differentiation and bone resorption. PloS one. 2022; 17(11):e0277307. doi: 10.1371/journal.pone.0277307. [PMID: 36395281]
  • Niraj Nepal, Subha Arthur, Molly R Butts, Soudamani Singh, Balasubramanian Palaniappan, Uma Sundaram. Molecular Mechanism of Stimulation of Na-K-ATPase by Leukotriene D4 in Intestinal Epithelial Cells. International journal of molecular sciences. 2021 Jul; 22(14):. doi: 10.3390/ijms22147569. [PMID: 34299188]
  • Neeraj Dholia, Gurupreet S Sethi, Amarjit S Naura, Umesh C S Yadav. Cysteinyl leukotriene D4 (LTD4) promotes airway epithelial cell inflammation and remodelling. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2021 Jan; 70(1):109-126. doi: 10.1007/s00011-020-01416-z. [PMID: 33136175]
  • Nosayba Al-Azzam, Lina Elsalem. Leukotriene D4 role in allergic asthma pathogenesis from cellular and therapeutic perspectives. Life sciences. 2020 Nov; 260(?):118452. doi: 10.1016/j.lfs.2020.118452. [PMID: 32956660]
  • 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]
  • Gwenaëlle Conseil, May Arama-Chayoth, Yossi Tsfadia, Susan P C Cole. Structure-guided probing of the leukotriene C4 binding site in human multidrug resistance protein 1 (MRP1; ABCC1). FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2019 10; 33(10):10692-10704. doi: 10.1096/fj.201900140r. [PMID: 31268744]
  • Eric E Figueroa, Meghan Kramer, Kevin Strange, Jerod S Denton. CysLT1 receptor antagonists pranlukast and zafirlukast inhibit LRRC8-mediated volume regulated anion channels independently of the receptor. American journal of physiology. Cell physiology. 2019 10; 317(4):C857-C866. doi: 10.1152/ajpcell.00281.2019. [PMID: 31390227]
  • Jun Miyata, Koichi Fukunaga, Yusuke Kawashima, Takashi Watanabe, Akina Saitoh, Tomomi Hirosaki, Yasutomo Araki, Toru Kikawada, Tomoko Betsuyaku, Osamu Ohara, Makoto Arita. Dysregulated fatty acid metabolism in nasal polyp-derived eosinophils from patients with chronic rhinosinusitis. Allergy. 2019 06; 74(6):1113-1124. doi: 10.1111/all.13726. [PMID: 30667533]
  • Fanny Lapointe, Sylvie Turcotte, Steeve Véronneau, Marek Rola-Pleszczynski, Jana Stankova. Role of Protein Tyrosine Phosphatase Epsilon (PTPε) in Leukotriene D4-Induced CXCL8 Expression. The Journal of pharmacology and experimental therapeutics. 2019 05; 369(2):270-281. doi: 10.1124/jpet.118.255422. [PMID: 30867226]
  • Nan Chiang, Ian R Riley, Jesmond Dalli, Ana R Rodriguez, Bernd W Spur, Charles N Serhan. New maresin conjugates in tissue regeneration pathway counters leukotriene D4-stimulated vascular responses. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2018 07; 32(7):4043-4052. doi: 10.1096/fj.201701493r. [PMID: 29490167]
  • Maged W Helmy, Mai M Helmy, Mahmoud M El-Mas. Enhanced lipoxygenase/LTD4 signaling accounts for the exaggerated hypertensive and nephrotoxic effects of cyclosporine plus indomethacin in rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Jun; 102(?):309-316. doi: 10.1016/j.biopha.2018.03.065. [PMID: 29571015]
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  • Mai M Helmy, Amel A Hashim, Samar M Mouneir. Zileuton alleviates acute cisplatin nephrotoxicity: Inhibition of lipoxygenase pathway favorably modulates the renal oxidative/inflammatory/caspase-3 axis. Prostaglandins & other lipid mediators. 2018 03; 135(?):1-10. doi: 10.1016/j.prostaglandins.2018.01.001. [PMID: 29355720]
  • Qian Zhang, Ying Xiong, Guo-Bing Li, Qin Tang, Min Cao, Jing-Bin Huang, Mao Xing, Chang-Peng Hu, Ya Gong, Qing-Hua Wang, Ning Gao, Rong Zhang. Xinqin exhibits the anti-allergic effect through the JAK2/STAT5 signaling pathway. Journal of ethnopharmacology. 2016 Dec; 193(?):466-473. doi: 10.1016/j.jep.2016.09.045. [PMID: 27666014]
  • Ana Lukic, Jie Ji, Helena Idborg, Bengt Samuelsson, Lena Palmberg, Susanne Gabrielsson, Olof Rådmark. Pulmonary epithelial cancer cells and their exosomes metabolize myeloid cell-derived leukotriene C4 to leukotriene D4. Journal of lipid research. 2016 09; 57(9):1659-69. doi: 10.1194/jlr.m066910. [PMID: 27436590]
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  • Kamila Syslová, Adéla Böhmová, Elvan Demirbağ, Kateřina Šimková, Marek Kuzma, Daniela Pelclová, Vratislav Sedlák, Petr Čáp, Pavel Martásek, Petr Kačer. Immunomagnetic molecular probe with UHPLC-MS/MS: a promising way for reliable bronchial asthma diagnostics based on quantification of cysteinyl leukotrienes. Journal of pharmaceutical and biomedical analysis. 2013 Jul; 81-82(?):108-17. doi: 10.1016/j.jpba.2013.03.026. [PMID: 23644905]
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  • Xiao Yun Wang, Su Su Tang, Mei Hu, Yan Long, Yong Qi Li, Ming Xing Liao, Hui Ji, Hao Hong. Leukotriene D4 induces amyloid-β generation via CysLT(1)R-mediated NF-κB pathways in primary neurons. Neurochemistry international. 2013 Feb; 62(3):340-7. doi: 10.1016/j.neuint.2013.01.002. [PMID: 23318673]
  • Barbro Dahlén, Federico P Gómez, Alejandro Casas, Peter H Howarth, Sven-Erik Dahlén, Robert Rodriguez-Roisin. Salbutamol but not ipratropium abolishes leukotriene D4-induced gas exchange abnormalities in asthma. European journal of clinical pharmacology. 2012 Oct; 68(10):1375-83. doi: 10.1007/s00228-012-1256-z. [PMID: 22457014]
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