1.0 2011-09-21 00:24:44 UTC 2015-07-21 06:57:31 UTC FDB023105 Leukotriene D4 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) 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)-L-cysteinyl)-glycine Leukotriene D LTD LTD4 C25H40N2O6S 496.66 496.260707712 (5S,6R,7E,9E)-6-({2-amino-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl}sulfanyl)-5-hydroxyicosa-7,9,11,14-tetraenoic acid (5S,6R,7E,9E)-6-{[2-amino-2-(carboxymethyl-C-hydroxycarbonimidoyl)ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid 73836-78-9 [H][C@](O)(CCCC(O)=O)[C@]([H])(SCC(N)C(=O)NCC(O)=O)\C=C\C=C\C=CCC=CCCCCC 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 YEESKJGWJFYOOK-DRETYUQKSA-N belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated. Leukotrienes Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic acyclic compounds Alpha amino acid amides Amino acids Carbonyl compounds Carboxylic acids Cysteine and derivatives Dialkylthioethers Dicarboxylic acids and derivatives Dipeptides Hydrocarbon derivatives Hydroxy fatty acids Hydroxyeicosatetraenoic acids Long-chain fatty acids Monoalkylamines N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Secondary alcohols Secondary carboxylic acid amides Sulfenyl compounds Thia fatty acids Unsaturated fatty acids Alcohol Aliphatic acyclic compound Alpha peptide Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-dipeptide Amine Amino acid Amino acid or derivatives Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Cysteine or derivatives Dialkylthioether Dicarboxylic acid or derivatives Fatty acid Hydrocarbon derivative Hydroxy fatty acid Hydroxyeicosatetraenoic acid Leukotriene Long-chain fatty acid N-acyl-alpha amino acid or derivatives N-acyl-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 Unsaturated fatty acid Solid logp 1.15 ALOGPS logs -5.31 ALOGPS solubility 2.41e-03 g/l ALOGPS logp 1.47 ChemAxon pka_strongest_acidic 3.23 ChemAxon pka_strongest_basic 9.2 ChemAxon iupac (5S,6R,7E,9E)-6-({2-amino-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl}sulfanyl)-5-hydroxyicosa-7,9,11,14-tetraenoic acid ChemAxon average_mass 496.66 ChemAxon mono_mass 496.260707712 ChemAxon smiles [H][C@](O)(CCCC(O)=O)[C@]([H])(SCC(N)C(=O)NCC(O)=O)\C=C\C=C\C=CCC=CCCCCC ChemAxon formula C25H40N2O6S ChemAxon 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 ChemAxon inchikey YEESKJGWJFYOOK-DRETYUQKSA-N ChemAxon polar_surface_area 153.44 ChemAxon refractivity 140.94 ChemAxon polarizability 56.21 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 HMDB03080 #<Reference:0x000055ce30340428> #<Reference:0x000055ce30340158> #<Reference:0x000055ce3032ff60> #<Reference:0x000055ce3032fda8> #<Reference:0x000055ce3032fbf0> #<Reference:0x000055ce3032fa38> #<Reference:0x000055ce3032f858> #<Reference:0x000055ce3032f380> #<Reference:0x000055ce3032f088> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Gamma-glutamyltransferase 5 P36269 GGT5 Gamma-glutamyltransferase 6 Q6P531 GGT6 Gamma-glutamyltransferase 7 Q9UJ14 GGT7 Gamma-glutamyltranspeptidase 1 P19440 GGT1