1.0 2011-09-21 00:14:41 UTC 2015-07-21 06:57:14 UTC FDB022480 5(S)-Hydroperoxyeicosatetraenoic acid 5(S)-Hydroperoxyeicosatetraenoic acid is a lipid hydroperoxide precursor of leukotrienes. The first step of biosynthesis of leukotrienes is conversion of arachidonic acid into 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid [5(S)-HpETE] by 5- lipoxygenases (5-LOX). Lipid hydroperoxides undergo homolytic decomposition into bifunctional electrophiles, which react with DNA bases to form DNA adducts. These DNA modifications are proposed to be involved in the etiology of cancer, cardiovascular disease, and neurodegeneration. 5-LOX, the enzyme responsible for the formation of 5(S)-HpETE in vivo, is expressed primarily in leukocytes, including monocytes and macrophages. Studies have implicated the 5-LOX pathway as an important mediator in the pathology of atherosclerosis. (PMID: 15777099) Endogenously generated 5-hydroperoxyeicosatetraenoic acid is the preferred substrate for human leukocyte leukotriene A4 synthase activity. Thus, the arachidonic acid moiety is preferentially converted to LTA4 in a concerted reaction without dissociation of a 5-HPETE intermediate. (PMID: 3036580) [HMDB] (5S,6e,8Z,11Z,14Z)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoate (5S,6e,8Z,11Z,14Z)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acid (6e,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoate (6e,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acid (S)-5-HPETE 5-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate 5-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid 5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate 5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid 5(S)-Hydroperoxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoate 5(S)-Hydroperoxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acid 5(S)-Hydroxyperoxy-6e,8Z,11Z,14Z-eicosatetraenoate 5(S)-Hydroxyperoxy-6e,8Z,11Z,14Z-eicosatetraenoic acid 5(S)-Hydroxyperoxy-6e,8Z,11Z,14Z-icosatetraenoate 5(S)-Hydroxyperoxy-6e,8Z,11Z,14Z-icosatetraenoic acid 5S-HpETE C20H32O4 336.4657 336.230059512 (5S,6E)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid (5S,6E)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid 71774-08-8 [H][C@@](CCCC(O)=O)(OO)\C=C\C=CCC=CCC=CCCCCC InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6?,10-9?,13-12?,16-14+/t19-/m1/s1 JNUUNUQHXIOFDA-MSFIICATSA-N belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds. Hydroperoxyeicosatetraenoic acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic acyclic compounds Alkyl hydroperoxides Allylic hydroperoxides Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroperoxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Peroxols Unsaturated fatty acids Aliphatic acyclic compound Alkyl hydroperoxide Allylic hydroperoxide Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroperoxide Hydroperoxy fatty acid Hydroperoxyeicosatetraenoic acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Peroxol Unsaturated fatty acid Solid logp 5.92 ALOGPS logs -5.32 ALOGPS solubility 1.61e-03 g/l ALOGPS logp 5.81 ChemAxon pka_strongest_acidic 4.39 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (5S,6E)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid ChemAxon average_mass 336.4657 ChemAxon mono_mass 336.230059512 ChemAxon smiles [H][C@@](CCCC(O)=O)(OO)\C=C\C=CCC=CCC=CCCCCC ChemAxon formula C20H32O4 ChemAxon inchi InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6?,10-9?,13-12?,16-14+/t19-/m1/s1 ChemAxon inchikey JNUUNUQHXIOFDA-MSFIICATSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 102.82 ChemAxon polarizability 39.98 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB01193 15632 #<Reference:0x000055ce2d040a28> #<Reference:0x000055ce2d040870> 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 Epididymal secretory glutathione peroxidase O75715 GPX5 Glutathione peroxidase 1 P07203 GPX1 Glutathione peroxidase 2 P18283 GPX2 Glutathione peroxidase 3 P22352 GPX3 Glutathione peroxidase 6 P59796 GPX6 Glutathione peroxidase 7 Q96SL4 GPX7 Phospholipid hydroperoxide glutathione peroxidase, mitochondrial P36969 GPX4