1.0 2011-09-21 00:22:21 UTC 2015-07-21 06:57:26 UTC FDB022956 Leukotriene B4 ethanolamide Leukotriene B4 ethanolamide is a synthetic agonist of leukotriene B4 (LTB4), that interacts with both leukotriene B4 receptors and Vanilloid TRPV1 receptors. Leukotriene B4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/ 15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted into human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before w-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. (PMID 17623009, 16207832) 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] LTB4 ethanol amide N-(2-hydroxyethyl)-5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraen-1-amide C22H37NO4 379.5335 379.272258677 (5S,12R)-5,12-dihydroxy-N-(2-hydroxyethyl)icosa-6,8,10,14-tetraenimidic acid (5S,12R)-5,12-dihydroxy-N-(2-hydroxyethyl)icosa-6,8,10,14-tetraenimidic acid 877459-63-7 [H]C(C=CC=C[C@]([H])(O)CC=CCCCCC)=C[C@@]([H])(O)CCCC(=O)NCCO InChI=1S/C22H37NO4/c1-2-3-4-5-6-9-13-20(25)14-10-7-8-11-15-21(26)16-12-17-22(27)23-18-19-24/h6-11,14-15,20-21,24-26H,2-5,12-13,16-19H2,1H3,(H,23,27)/t20-,21-/m1/s1 DQLVVNIINUTUIU-NHCUHLMSSA-N belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine. N-acylethanolamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives N-acyl amines Organic oxides Organopnictogen compounds Primary alcohols Secondary alcohols Secondary carboxylic acid amides Alcohol Aliphatic acyclic compound Carbonyl group Carboxamide group Carboxylic acid derivative Fatty acyl Fatty amide Hydrocarbon derivative N-acyl-amine N-acylethanolamine Organic oxide Organic oxygen compound Organooxygen compound Organopnictogen compound Primary alcohol Secondary alcohol Secondary carboxylic acid amide Liquid logp 4.24 ALOGPS logs -4.66 ALOGPS solubility 8.36e-03 g/l ALOGPS logp 3.67 ChemAxon pka_strongest_acidic 6.26 ChemAxon pka_strongest_basic 4.21 ChemAxon iupac (5S,12R)-5,12-dihydroxy-N-(2-hydroxyethyl)icosa-6,8,10,14-tetraenimidic acid ChemAxon average_mass 379.5335 ChemAxon mono_mass 379.272258677 ChemAxon smiles [H]C(C=CC=C[C@]([H])(O)CC=CCCCCC)=C[C@@]([H])(O)CCCC(=O)NCCO ChemAxon formula C22H37NO4 ChemAxon inchi InChI=1S/C22H37NO4/c1-2-3-4-5-6-9-13-20(25)14-10-7-8-11-15-21(26)16-12-17-22(27)23-18-19-24/h6-11,14-15,20-21,24-26H,2-5,12-13,16-19H2,1H3,(H,23,27)/t20-,21-/m1/s1 ChemAxon inchikey DQLVVNIINUTUIU-NHCUHLMSSA-N ChemAxon polar_surface_area 93.28 ChemAxon refractivity 116.52 ChemAxon polarizability 47.54 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB02304 #<Reference:0x000055ce324e8850> #<Reference:0x000055ce324e8670> #<Reference:0x000055ce324e8490> 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