1.0 2011-09-21 00:32:38 UTC 2015-07-21 06:57:47 UTC FDB023628 11-trans-Leukotriene C4 11-trans-Leukotriene C4 (11-trans-LTC4) is leukotriene derivative formed by the metabolism of LTA4 and is found in human endothelial cells. Leukotrienes (LT) are a family of naturally occurring lipids that are oxygenated metabolites of arachidonic acid. Biosynthesis of the leukotrienes involves the action of a lipoxygenase on arachidonate to yield a hydroperoxy intermediate which is then dehydrated to the allylic epoxide, LTA4. LTA4 can be hydrolyzed to the dihydroxy acid, LTB4 or it can be conjugated with glutathione (GSH) to produce the parent slow reacting substance, LTC4. The leukotrienes are mediators of inflammation, hypersensitivy reactions, and respiratory disorders. On a cellular level, LTC4 and its metabolites, LTD4 and LTE4, are potent constrictors of vascular bronchial smooth muscle. LTC4 and LTD4 also induce plasma leakage from the microvasculature. LTB4 is a potent polymorphonuclear leukocyte (PMNL) chemotaxin and induces neutrophils to degranulate, generate superoxide, and adhere to vascular endothelium. Several investigations of leukotriene synthesis by blood vessels and cultured vascular cells have been undertaken. Vascular preparations have been shown to produce LTB4 and LTC4 and to metabolize LTC4 to LTD4 and LTE4. In addition, mast cells, macrophages, and PMNL, all of which may contaminate whole vessel preparations, are known to synthesize both peptide-containing and dihydroxy acid leukotrienes. Consequently, it is unclear what cells are contributing to vascular leukotriene synthesis. No evidence of isolated vascular cell leukotriene synthesis is currently available. Indeed, this report and others have been unable to detect endothelial cell conversion of arachidonic acid to the leukotrienes. The fact that vascular endothelium lacks the full complement of leukotriene biosynthetic enzymes does not preclude an active role for this tissue in leukotriene metabolism. In some cases, tissues which are not known to synthesize leukotrienes from arachidonate are able to catalyze one or more of the intermediate steps of the pathway. In the present investigation, the leukotriene metabolism of porcine aortic endothelium has been studied. Evidence is presented which indicates that endothelial cells are unable to convert arachidonic acid to LTC4 but, nevertheless, contain LTC4 synthetase. Additional experiments suggest that a neutrophil- endothelial cell interaction augments vascular LTC4 synthesis by the intercellular transfer of LTA4 from PMNL to endothelial cells. (PMID 3023351) 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,E,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,E,Z)]]-N-[S-[1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl]-N-L-gamma-glutamyl-L-cysteinyl]-Glycine 11-trans-LTC4 5S-hydroxy-6R-(S-glutathionyl)-7E,9E,11E14Z-eicosatetraenoate 5S-hydroxy-6R-(S-glutathionyl)-7E,9E,11E14Z-eicosatetraenoic acid Leukotriene C2 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 74841-69-3 [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 HMDB05095 #<Reference:0x000055ce31763a18> #<Reference:0x000055ce31763810> 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