1.0 2011-09-21 00:14:44 UTC 2015-07-21 06:57:14 UTC FDB022484 Leukotriene C4 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, mucous 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 signaling pathways. [HMDB] (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 (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-gamma-glutamyl-L-cysteinyl]-Glycine 5S,6R-LTC4 5S-hydroxy,6R-(S-glutathionyl),7E,9E,11Z,14Z-eicosatetraenoate 5S-hydroxy,6R-(S-glutathionyl),7E,9E,11Z,14Z-eicosatetraenoic acid 5S,6R-Ltc 5S,6R-Ltc(sub 4) L-gamma-glutamyl-S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]-2,4,6,9-pentadecatetraenyl]-L-cysteinyl-glycine Leucotriene C4 Leukotriene C Leukotriene C1 Leukotriene C4 LTC LTC (sub 4) LTC4 C30H47N3O9S 625.774 625.303300807 (5S,6R)-6-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid (5S,6R)-6-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-(carboxymethyl-C-hydroxycarbonimidoyl)ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid 72025-60-6 [H][C@](N)(CCC(=O)N[C@@]([H])(CS[C@]([H])(C=CC=CC=CCC=CCCCCC)[C@@]([H])(O)CCCC(O)=O)C(=O)NCC(O)=O)C(O)=O 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)/t22-,23-,24-,25+/m0/s1 GWNVDXQDILPJIG-OJJQZRKESA-N belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Oligopeptides Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Alpha amino acid amides Amino acids Carbonyl compounds Carboxylic acids Cysteine and derivatives Dialkylthioethers Gamma-glutamyl peptides Glutamine and derivatives Hydrocarbon derivatives Hydroxy fatty acids Hydroxyeicosatetraenoic acids L-alpha-amino acids Leukotrienes Monoalkylamines N-acyl amines N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Secondary alcohols Secondary carboxylic acid amides Sulfenyl compounds Thia fatty acids Tricarboxylic acids and derivatives Alcohol Aliphatic acyclic compound Alpha-amino acid Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-oligopeptide Amine Amino acid Amino acid or derivatives Carbonyl group Carboxamide group Carboxylic acid Cysteine or derivatives Dialkylthioether Eicosanoid Fatty acyl Fatty amide Gamma-glutamyl alpha peptide Glutamine or derivatives Hydrocarbon derivative Hydroxy fatty acid Hydroxyeicosatetraenoic acid L-alpha-amino acid Leukotriene N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine N-substituted-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Secondary alcohol Secondary carboxylic acid amide Sulfenyl compound Thia fatty acid Thioether Tricarboxylic acid or derivatives Solid logp 0.57 ALOGPS logs -5.34 ALOGPS solubility 2.88e-03 g/l ALOGPS logp 1.54 ChemAxon pka_strongest_acidic 1.97 ChemAxon pka_strongest_basic 9.54 ChemAxon iupac (5S,6R)-6-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid ChemAxon average_mass 625.774 ChemAxon mono_mass 625.303300807 ChemAxon smiles [H][C@](N)(CCC(=O)N[C@@]([H])(CS[C@]([H])(C=CC=CC=CCC=CCCCCC)[C@@]([H])(O)CCCC(O)=O)C(=O)NCC(O)=O)C(O)=O ChemAxon formula C30H47N3O9S ChemAxon 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)/t22-,23-,24-,25+/m0/s1 ChemAxon inchikey GWNVDXQDILPJIG-OJJQZRKESA-N ChemAxon polar_surface_area 223.33 ChemAxon refractivity 169.55 ChemAxon polarizability 69.34 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 12 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 HMDB01198 16978 #<Reference:0x000055ce317a8de8> #<Reference:0x000055ce317a8be0> #<Reference:0x000055ce317a8a00> #<Reference:0x000055ce317a8848> #<Reference:0x000055ce317a8640> #<Reference:0x000055ce317a8488> #<Reference:0x000055ce317a82d0> #<Reference:0x000055ce317a80f0> #<Reference:0x000055ce317a7f10> #<Reference:0x000055ce317a7d58> #<Reference:0x000055ce317a7ba0> #<Reference:0x000055ce317a79e8> #<Reference:0x000055ce317a7808> #<Reference:0x000055ce317a7628> #<Reference:0x000055ce317a7470> #<Reference:0x000055ce317a7218> #<Reference:0x000055ce317a7060> #<Reference:0x000055ce317a6e80> #<Reference:0x000055ce317a6cc8> #<Reference:0x000055ce317a6ae8> #<Reference:0x000055ce317a6908> Gamma-glutamyltransferase 5 P36269 GGT5 Gamma-glutamyltransferase 6 Q6P531 GGT6 Gamma-glutamyltransferase 7 Q9UJ14 GGT7 Gamma-glutamyltranspeptidase 1 P19440 GGT1 Leukotriene C4 synthase Q16873 LTC4S