Leukotriene C4 (BioDeep_00000003314)

 

Secondary id: BioDeep_00000028044, BioDeep_00000410648

human metabolite Endogenous blood metabolite


代谢物信息卡片


(5S,6R,7E,9E,11Z, 14Z)-6-[(2R)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-3- (carboxymethylamino)-3-oxopropyl]sulfanyl-5-hydroxyicosa-7,9,11, 14-tetraenoic acid

化学式: C30H47N3O9S (625.3033)
中文名称: 白三烯C4
谱图信息: 最多检出来源 Homo sapiens(blood) 14.1%

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)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
InChI: InChI=1S/C30H47N3O9S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-25(24(34)15-14-17-27(36)37)43-21-23(29(40)32-20-28(38)39)33-26(35)19-18-22(31)30(41)42/h6-7,9-13,16,22-25,34H,2-5,8,14-15,17-21,31H2,1H3,(H,32,40)(H,33,35)(H,36,37)(H,38,39)(H,41,42)/b7-6-,10-9-,12-11+,16-13+/t22-,23-,24-,25+/m0/s1

描述信息

Leukotriene C4 (LTC4) is a cysteinyl leukotriene (CysLT), a family of potent inflammatory mediators. Eosinophils, one of the principal cell types recruited to and activated at sites of allergic inflammation, is capable of elaborating lipid mediators, including leukotrienes derived from the oxidative metabolism of arachidonic acid (AA). Potentially activated eosinophils may elaborate greater quantities of LTC4, than normal eosinophils. These activated eosinophils thus are primed for enhanced LTC4 generation in response to subsequent stimuli. Some recognized priming stimuli are chemoattractants (e.g. eotaxin, PAF) that may participate in the recruitment of eosinophils to sites of allergic inflammation. The mechanisms by which chemoattractants and other activating cytokines (e.g. interleukin (IL)-5) or extracellular matrix components (e.g. fibronectin) enhance eosinophil eicosanoid formation are pertinent to the functions of these eicosanoids as paracrine mediators of allergic inflammation. Some eosinophil-derived eicosanoids may be active in down-regulating inflammation. It is increasingly likely that eicosanoids synthesized within cells, including eosinophils, may have intracellular (e.g. intracrine) roles in regulating cell functions, in addition to the more recognized activities of eicosanoids as paracrine mediators of inflammation. Acting extracellularly, the cysteinyl leukotrienes (CysLTs) LTC4 and its extracellular derivatives, LTD4 and LTE4 are key paracrine mediators pertinent to asthma and allergic diseases. Based on their receptor-mediated capabilities, they can elicit bronchoconstriction, mucus hypersecretion, bronchial hyperresponsiveness, increased microvascular permeability, and additional eosinophil infiltration. Eosinophils are a major source of CysLTs and have been identified as the principal LTC4 synthase expressing cells in bronchial mucosal biopsies of asthmatic subjects (PMID: 12895596). 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 c4, also known as ltc4 or 5s,6r-ltc(sub 4), is a member of the class of compounds known as oligopeptides. Oligopeptides are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Thus, leukotriene c4 is considered to be an eicosanoid lipid molecule. Leukotriene c4 is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Leukotriene c4 can be synthesized from icosa-7,9,11,14-tetraenoic acid. Leukotriene c4 is also a parent compound for other transformation products, including but not limited to, leukotriene C4 methyl ester, 11,12-dihydro-(12R)-hydroxyleukotriene C4, and 11,12-dihydro-12-oxoleukotriene C4. Leukotriene c4 can be found in a number of food items such as gram bean, maitake, caraway, and burbot, which makes leukotriene c4 a potential biomarker for the consumption of these food products. Leukotriene c4 can be found primarily in blood and cerebrospinal fluid (CSF), as well as throughout most human tissues. In humans, leukotriene c4 is involved in several metabolic pathways, some of which include trisalicylate-choline action pathway, antipyrine action pathway, nepafenac action pathway, and fenoprofen action pathway. Leukotriene c4 is also involved in a couple of metabolic disorders, which include leukotriene C4 synthesis deficiency and tiaprofenic acid action pathway. Moreover, leukotriene c4 is found to be associated with eczema. Leukotriene C4 (LTC4) is a leukotriene. LTC4 has been extensively studied in the context of allergy and asthma. In cells of myeloid origin such as mast cells, its biosynthesis is orchestrated by translocation to the nuclear envelope along with co-localization of cytosolic phospholipase A2 (cPLA2), Arachidonate 5-lipoxygenase (5-LO), 5-lipoxygenase-activating protein (FLAP) and LTC4 synthase (LTC4S), which couples glutathione to an LTA4 intermediate.The MRP1 transporter then secretes cytosolic LTC4 and cell surface proteases further metabolize it by sequential cleavage of the γ-glutamyl and glycine residues off its glutathione segment, generating the more stable products LTD4 and LTE4. All three leukotrienes then bind at different affinities to two G-protein coupled receptors: CYSLTR1 and CYSLTR2, triggering pulmonary vasoconstriction and bronchoconstriction .

同义名列表

28 个代谢物同义名

(5S,6R,7E,9E,11Z, 14Z)-6-[(2R)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-3- (carboxymethylamino)-3-oxopropyl]sulfanyl-5-hydroxyicosa-7,9,11, 14-tetraenoic acid; (5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-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]-N-L-gamma-glutamyl-L-cysteinyl]-glycine 5S,6R-LTC4; (R-(R*,s*-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-gamma-glutamyl-L-cysteinyl)-glycine; (R-(R*,s*-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-gamma-glutamyl-L-cysteinyl)glycine; (R-(R*,s*-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-γ-glutamyl-L-cysteinyl)glycine; (R-(R*,s*-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-g-glutamyl-L-cysteinyl)glycine; L-gamma-Glutamyl-S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]-2,4,6,9-pentadecatetraenyl]-L-cysteinyl-glycine; 5S-Hydroxy,6R-(S-glutathionyl),7E,9E,11Z,14Z-eicosatetraenoic acid; 5S-Hydroxy,6R-(S-glutathionyl),7E,9E,11Z,14Z-eicosatetraenoate; 11-trans Leukotriene C4; 5S,6R-LTC(Sub 4); Leukotriene C 1; Leukotriene C-4; Leukotriene C 4; Leukotriene C-1; Leukotriene C4; leukotriene-C4; Leukotrienes C; Leucotriene C4; Leukotriene C1; Leukotriene C; LTC (Sub 4); 5S,6R-LTC4; 5S,6R-LTC; LTC4; LTC; Leukotriene C4



数据库引用编号

31 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(11)

BioCyc(0)

PlantCyc(0)

代谢反应

215 个相关的代谢反应过程信息。

Reactome(159)

BioCyc(3)

WikiPathways(6)

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。

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 5 ALOX5, IL13, KAT5, MAPK14, PTGS2
Peripheral membrane protein 2 ALOX5, PTGS2
Endoplasmic reticulum membrane 2 MGST2, PTGS2
Nucleus 2 KAT5, MAPK14
cytosol 3 ALOX5, KAT5, MAPK14
nucleoplasm 3 ALOX5, KAT5, MAPK14
Cell membrane 3 ABCC1, CYSLTR2, TNF
Multi-pass membrane protein 5 ABCC1, ABCC2, ABCC3, CYSLTR2, MGST2
cell surface 2 ABCC2, TNF
glutamatergic synapse 1 MAPK14
neuronal cell body 1 TNF
Cytoplasm, cytosol 1 ALOX5
plasma membrane 9 ABCC1, ABCC2, ABCC3, CYSLTR1, CYSLTR2, IFNLR1, IGHE, MGST2, TNF
Membrane 6 ABCC1, ABCC2, ABCC3, CYSLTR1, IFNLR1, MGST2
apical plasma membrane 2 ABCC1, ABCC2
basolateral plasma membrane 2 ABCC1, ABCC3
caveola 1 PTGS2
extracellular exosome 1 ABCC1
endoplasmic reticulum 2 MGST2, PTGS2
extracellular space 10 ALOX5, IGHE, IL10, IL13, IL2, IL3, IL4, IL5, RNASE3, TNF
perinuclear region of cytoplasm 2 ALOX5, KAT5
intercellular canaliculus 1 ABCC2
mitochondrion 1 MAPK14
protein-containing complex 1 PTGS2
intracellular membrane-bounded organelle 2 KAT5, MGST2
Microsome membrane 2 MGST2, PTGS2
Single-pass type I membrane protein 2 IFNLR1, IGHE
Secreted 6 IL10, IL13, IL2, IL3, IL4, IL5
extracellular region 11 ALOX5, IGHE, IL10, IL13, IL2, IL3, IL4, IL5, MAPK14, RNASE3, TNF
transcription regulator complex 1 KAT5
Nucleus membrane 1 ALOX5
nuclear membrane 1 ALOX5
external side of plasma membrane 2 IL13, TNF
nucleolus 1 KAT5
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 ABCC2
Cytoplasm, perinuclear region 2 ALOX5, KAT5
Membrane raft 1 TNF
lateral plasma membrane 1 ABCC1
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
chromatin 1 KAT5
IgE immunoglobulin complex 1 IGHE
phagocytic cup 1 TNF
Chromosome 1 KAT5
Nucleus, nucleolus 1 KAT5
spindle pole 1 MAPK14
NuA4 histone acetyltransferase complex 1 KAT5
Basolateral cell membrane 1 ABCC3
[Isoform 2]: Cell membrane 1 IGHE
site of double-strand break 1 KAT5
Cytoplasm, cytoskeleton, spindle pole 1 KAT5
nuclear envelope 2 ALOX5, MGST2
Nucleus envelope 1 ALOX5
Chromosome, centromere, kinetochore 1 KAT5
basal plasma membrane 2 ABCC1, ABCC3
ficolin-1-rich granule lumen 2 ALOX5, MAPK14
secretory granule lumen 2 ALOX5, MAPK14
endoplasmic reticulum lumen 1 PTGS2
nuclear matrix 1 ALOX5
kinetochore 1 KAT5
mitotic spindle pole 1 KAT5
azurophil granule lumen 1 RNASE3
Nucleus matrix 1 ALOX5
nuclear envelope lumen 1 ALOX5
Basal cell membrane 1 ABCC3
histone acetyltransferase complex 1 KAT5
nucleosome 1 KAT5
Swr1 complex 1 KAT5
[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 intermembrane space 1 ALOX5
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
piccolo histone acetyltransferase complex 1 KAT5


文献列表

  • Yuanfeng Shen, Entezar Mehrabi Nasab, Fatemeh Hassanpour, Seyyed Shamsadin Athari. The Effects of Combined Therapeutic Protocol on Allergic Rhinitis Symptoms and Molecular Determinants. Iranian journal of allergy, asthma, and immunology. 2022 Apr; 21(2):141-150. doi: 10.18502/ijaai.v21i2.9222. [PMID: 35490268]
  • 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]
  • Remo Poto, Isabella Quinti, Gianni Marone, Maurizio Taglialatela, Amato de Paulis, Vincenzo Casolaro, Gilda Varricchi. IgG Autoantibodies Against IgE from Atopic Dermatitis Can Induce the Release of Cytokines and Proinflammatory Mediators from Basophils and Mast Cells. Frontiers in immunology. 2022; 13(?):880412. doi: 10.3389/fimmu.2022.880412. [PMID: 35711458]
  • Tatsuro Nakamura. The roles of lipid mediators in type I hypersensitivity. Journal of pharmacological sciences. 2021 Sep; 147(1):126-131. doi: 10.1016/j.jphs.2021.06.001. [PMID: 34294363]
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  • Junmei He, Zhongjie Han, Qurat Ul Ain Farooq, Chunhua Li. Study on functional sites in human multidrug resistance protein 1 (hMRP1). Proteins. 2021 06; 89(6):659-670. doi: 10.1002/prot.26049. [PMID: 33469960]
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  • Xiao Tang, David Fuchs, Shuai Tan, Mette Trauelsen, Thue W Schwartz, Craig E Wheelock, Nailin Li, Jesper Z Haeggström. Activation of metabolite receptor GPR91 promotes platelet aggregation and transcellular biosynthesis of leukotriene C4. Journal of thrombosis and haemostasis : JTH. 2020 04; 18(4):976-984. doi: 10.1111/jth.14734. [PMID: 31930602]
  • Wei Fang, ChenHui Li, QingQing Wu, ZhaoMin Yao, Jie Wu, Peng Huang, DianLei Wang, ZeGeng Li. Metabolic profiling of chronic obstructive pulmonary disease model rats and the interventional effects of HuaTanJiangQi decoction using UHPLC-Q-TOF/MSE. Journal of pharmaceutical and biomedical analysis. 2020 Feb; 180(?):113078. doi: 10.1016/j.jpba.2019.113078. [PMID: 31911286]
  • Beatriz Sastre, María Luz García-García, Cristina Calvo, Inmaculada Casas, José Manuel Rodrigo-Muñoz, José Antonio Cañas, Inés Mora, Victoria Del Pozo. Immune recovery following bronchiolitis is linked to a drop in cytokine and LTC4 levels. Pediatric research. 2020 02; 87(3):581-587. doi: 10.1038/s41390-019-0606-2. [PMID: 31600771]
  • Zhiyong Wu, Chunli Chen, Qiaomei Zhang, Jiaxin Bao, Qianqian Fan, Rui Li, Muhammad Ishfaq, Jichang Li. Arachidonic acid metabolism is elevated in Mycoplasma gallisepticum and Escherichia coli co-infection and induces LTC4 in serum as the biomarker for detecting poultry respiratory disease. Virulence. 2020 01; 11(1):730-738. doi: 10.1080/21505594.2020.1772653. [PMID: 32441188]
  • 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]
  • A A Szczepańska, M Łupicka, A J Korzekwa. Do arachidonic acid metabolites affect apoptosis in bovine endometrial cells with silenced PPAR genes?. Prostaglandins & other lipid mediators. 2019 08; 143(?):106336. doi: 10.1016/j.prostaglandins.2019.106336. [PMID: 31112752]
  • Ryota Uchida, Tomonori Egawa, Yoshio Fujita, Kazuyuki Furuta, Hiroaki Taguchi, Satoshi Tanaka, Keigo Nishida. Identification of the minimal region of peptide derived from ADP-ribosylation factor1 (ARF1) that inhibits IgE-mediated mast cell activation. Molecular immunology. 2019 01; 105(?):32-37. doi: 10.1016/j.molimm.2018.11.002. [PMID: 30472514]
  • Yoshihide Kanaoka, K Frank Austen. Roles of cysteinyl leukotrienes and their receptors in immune cell-related functions. Advances in immunology. 2019; 142(?):65-84. doi: 10.1016/bs.ai.2019.04.002. [PMID: 31296303]
  • Menachem Rubinstein, Efrat Dvash. Leukotrienes and kidney diseases. Current opinion in nephrology and hypertension. 2018 01; 27(1):42-48. doi: 10.1097/mnh.0000000000000381. [PMID: 29059080]
  • Natália R T Amorim, Tatiana Luna-Gomes, Marcos Gama-Almeida, Glaucia Souza-Almeida, Claudio Canetti, Bruno L Diaz, Peter F Weller, Patricia Torres Bozza, Clarissa M Maya-Monteiro, Christianne Bandeira-Melo. Leptin Elicits LTC4 Synthesis by Eosinophils Mediated by Sequential Two-Step Autocrine Activation of CCR3 and PGD2 Receptors. Frontiers in immunology. 2018; 9(?):2139. doi: 10.3389/fimmu.2018.02139. [PMID: 30298073]
  • Anuradha Rajamanickam, Saravanan Munisankar, Yukthi Bhootra, Chandra Kumar Dolla, Thomas B Nutman, Subash Babu. Elevated Systemic Levels of Eosinophil, Neutrophil, and Mast Cell Granular Proteins in Strongyloides Stercoralis Infection that Diminish following Treatment. Frontiers in immunology. 2018; 9(?):207. doi: 10.3389/fimmu.2018.00207. [PMID: 29479356]
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