1.0 2011-09-21 00:32:37 UTC 2015-07-21 06:57:47 UTC FDB023627 12(S)-Leukotriene B4 12(S)-Leukotriene B4 is an agonist of G-protein-coupled receptors for leukotriene B4 (LTB4), BLT1 and BLT2. 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. (PMID: 7649996, 17623009, 2866160, 15866883) 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] [S-[R*,R*-(E,Z,E,Z)]]-5,12-dihydroxy-6,8,10,14-Eicosatetraenoate [S-[R*,R*-(E,Z,E,Z)]]-5,12-dihydroxy-6,8,10,14-Eicosatetraenoic acid 12S-LTB4 2-epi-LTB4 5(S),12(S)-Dihydroxyeicosatetraenoate 5(S),12(S)-Dihydroxyeicosatetraenoic acid 5S,12S-Dihydroxy-6Z,8e,10e,14Z-eicosatetraenoate 5S,12S-Dihydroxy-6Z,8e,10e,14Z-eicosatetraenoic acid 5S,12S-dihydroxy-6Z,8E,10E,14Z-eicsatetraenoate 5S,12S-dihydroxy-6Z,8E,10E,14Z-eicsatetraenoic acid C20H32O4 336.4657 336.230059512 (5S,12S)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid (5S,12S)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid 83709-73-3 [H]C(C=CC=C[C@@]([H])(O)CC=CCCCCC)=C[C@@]([H])(O)CCCC(O)=O InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/t18-,19+/m0/s1 VNYSSYRCGWBHLG-RBUKOAKNSA-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 Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Hydroxyeicosatetraenoic acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroxy fatty acid Hydroxyeicosatetraenoic acid Leukotriene Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Solid logp 5.46 ALOGPS logs -4.34 ALOGPS solubility 1.52e-02 g/l ALOGPS logp 4.13 ChemAxon pka_strongest_acidic 4.65 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (5S,12S)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid ChemAxon average_mass 336.4657 ChemAxon mono_mass 336.230059512 ChemAxon smiles [H]C(C=CC=C[C@@]([H])(O)CC=CCCCCC)=C[C@@]([H])(O)CCCC(O)=O ChemAxon formula C20H32O4 ChemAxon inchi InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/t18-,19+/m0/s1 ChemAxon inchikey VNYSSYRCGWBHLG-RBUKOAKNSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 102.98 ChemAxon polarizability 41.4 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB05089 #<Reference:0x000055ce317d4dd0> #<Reference:0x000055ce317d4c18> #<Reference:0x000055ce317d4a60> #<Reference:0x000055ce317d48a8> #<Reference:0x000055ce317d46f0> 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