1.0 2011-09-21 00:17:36 UTC 2015-07-21 06:57:17 UTC FDB022663 20-Hydroxy-leukotriene B4 20-hydroxy- Leukotriene B4 (20-OH-LTB4) is an omega-hydroxylated metabolite of leukotriene B4 in human neutrophils. Elevated urinary concentrations of 20-OH-LTB4 and LTB4 are found in patients with Sjogren-Larsson syndrome (SLS, OMIM 270220), an autosomal recessively inherited neurocutaneous disorder caused by a deficiency of the microsomal enzyme fatty aldehyde dehydrogenase (FALDH), which as an essential role in LTB4 metabolism. Preterm birth seems to be one of the features of the syndrome. The reason for the preterm birth is unclear. It is hypothesized that it relates to the defective LTB4 degradation in SLS. The pathological urinary excretion of LTB4 and 20-OH-LTB4 is a biochemical marker for SLS. Surprisingly, 20-OH-LTB4 concentrations are normal in CSF. 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: 12709426, 9799565, 11408337, 17623009) 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] (5S,12R)-5,12,20-Trihydroxy-(6Z,8E,10E,14Z)-eicosatetraenoate (5S,12R)-5,12,20-Trihydroxy-(6Z,8E,10E,14Z)-eicosatetraenoic acid (5S,6Z,8E,10E,12R,14Z)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate (5S,6Z,8E,10E,12R,14Z)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid (6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyeicosa-6,8,10,14-tetraenoate (6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyeicosa-6,8,10,14-tetraenoic acid (6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoate (6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoic acid [S-[R*,S*-(E,Z,E,Z)]]-5,12,20-trihydroxy-6,8,10,14-Eicosatetraenoate [S-[R*,S*-(E,Z,E,Z)]]-5,12,20-trihydroxy-6,8,10,14-Eicosatetraenoic acid 20-hydroxy LTB4 20-Hydroxy-leukotriene B4 20-Hydroxy-LTB4 20-hydroxyleukotriene B4 20-OH-5S,12S-dihydroxy-6,10-trans-8,14-cis-eicosatetraenoate 20-OH-5S,12S-dihydroxy-6,10-trans-8,14-cis-eicosatetraenoic acid 20-OH-Leukotriene B4 20-OH-LTB4 5,12,20-THETE 5,12,20-TriHETE 5S,12R,20-trihydroxy-6Z,8E,10E,14Z-eicosatetraenoate 5S,12R,20-trihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid omega-Hydroxy-LTB4 w-Hydroxy-LTB4 C20H32O5 352.4651 352.224974134 (5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid (5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid 79516-82-8 [H]C(C=CC=C[C@]([H])(O)CC=CCCCCCO)=C[C@@]([H])(O)CCCC(O)=O InChI=1S/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/t18-,19-/m1/s1 PTJFJXLGRSTECQ-RTBURBONSA-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 Polyols Primary alcohols 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 Polyol Primary alcohol Secondary alcohol Unsaturated fatty acid Liquid logp 4.22 ALOGPS logs -4.03 ALOGPS solubility 3.30e-02 g/l ALOGPS logp 2.69 ChemAxon pka_strongest_acidic 4.65 ChemAxon pka_strongest_basic -1.2 ChemAxon iupac (5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid ChemAxon average_mass 352.4651 ChemAxon mono_mass 352.224974134 ChemAxon smiles [H]C(C=CC=C[C@]([H])(O)CC=CCCCCCO)=C[C@@]([H])(O)CCCC(O)=O ChemAxon formula C20H32O5 ChemAxon inchi InChI=1S/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/t18-,19-/m1/s1 ChemAxon inchikey PTJFJXLGRSTECQ-RTBURBONSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 104.91 ChemAxon polarizability 42.67 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 HMDB01509 #<Reference:0x000055ce30a7b440> #<Reference:0x000055ce30a7b1e8> #<Reference:0x000055ce30a7afe0> #<Reference:0x000055ce30a7add8> #<Reference:0x000055ce30a7aae0> #<Reference:0x000055ce30a7a8b0> 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