1.0 2011-09-21 00:35:52 UTC 2018-05-28 18:37:32 UTC FDB023857 18-Hydroxyarachidonic acid (18R)-Hydroxyarachidonate is a substrate for CYP4F8 or leukotriene-B4 20-monooxygenase (EC 1.14.13.30). This enzyme hydroxylates arachdonic acid (20:4n-6) to (18R)-hydroxyarachidonate in the endoplasmic reticulum. This reaction is irreversible. CYP4F8 is a member of the cytochrome P450 superfamily of enzymes. The cytochrome P450 proteins are monooxygenases which catalyze many reactions involved in drug metabolism and synthesis of cholesterol, steroids and other lipids. This protein localizes to the endoplasmic reticulum and functions as a 19-hydroxylase of prostaglandins in seminal vesicles. In particular, CYP4F8 catalyzes the 2-hydroxylation of PGH1 and PGH2, which will lead to biosynthesis of the two main PGs of human seminal fluid, (19R)-hydroxy-PGE1 and (19R)-hydroxy-PGE2 (PMID: 10791960). 18-Hydroxyarachidonic acid is an intermediate in eicosanoid metabolism. [HMDB] (18R)-Hydroxyarachidonate (18R)-Hydroxyarachidonic acid 18-HETE 18-Hydroxyarachidonate 18-hydroxyarachidonic acid 18-Hydroxyeicosatetraenoate 18-Hydroxyeicosatetraenoic acid 18(R)-Hydroxyeicosatetraenoate 18(R)-Hydroxyeicosatetraenoic acid omega-Hydroxyarachidonic acid w-Hydroxyarachidonic acid C20H32O3 320.4663 320.23514489 (18R)-18-hydroxyicosa-5,8,11,14-tetraenoic acid (18R)-18-hydroxyicosa-5,8,11,14-tetraenoic acid 124411-81-0 [H][C@@](O)(CC)CCC=CCC=CCC=CCC=CCCCC(O)=O InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/t19-/m1/s1 PPCHNRUZQWLEMF-LJQANCHMSA-N belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds. Hydroxyeicosatetraenoic acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty 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 Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Solid logp 5.81 ALOGPS logs -5.20 ALOGPS solubility 2.00e-03 g/l ALOGPS logp 5.2 ChemAxon pka_strongest_acidic 4.82 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (18R)-18-hydroxyicosa-5,8,11,14-tetraenoic acid ChemAxon average_mass 320.4663 ChemAxon mono_mass 320.23514489 ChemAxon smiles [H][C@@](O)(CC)CCC=CCC=CCC=CCC=CCCCC(O)=O ChemAxon formula C20H32O3 ChemAxon inchi InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/t19-/m1/s1 ChemAxon inchikey PPCHNRUZQWLEMF-LJQANCHMSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 101.62 ChemAxon polarizability 38.15 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB06245 #<Reference:0x000055ce31e8eba8> 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