1.0 2011-09-21 00:34:50 UTC 2018-05-29 01:53:08 UTC FDB023796 20-Hydroxyeicosatetraenoic acid Metabolite produced during NADPH dependent enzymatic oxidation of arachidonic acid. Potent vasoconstrictor [CCD] 20-Hydroxyeicosatetraenoic acid (20-HETE) is a metabolite of arachidonic acid. Cytochrome P450 enzymes of the 4A and 4F families catalyze the omega-hydroxylation of arachidonic acid and produce 20-HETE. 20-HETE is a potent constrictor or renal, cerebral and mesenteric arteries. The vasoconstrictor response to 20-HETE is associated with activation of protein kinase, Rho kinase and the mitogen activated protein (MAP) kinase pathway C. 20-HETE also increases intracellular Ca2+ by causing the depolarization of vascular smooth muscle membrane secondary to blocking the large-conductance Ca2+-activated K+-channels and by a direct effect on L-type Ca channels. Elevations in the production of 20-HETE mediate the myogenic response of skeletal, renal and cerebral arteries to elevations in transmural pressure. There is an important interaction between nitric oxide (NO) and the formation of 20-HETE production. NO inhibits the formation of 20-HETE formation in renal and cerebral arteries and that a fall in levels of 20-HETE contributes the cyclic GMP-independent dilator effect of NO to activate the large-conductance Ca2+-activated K+-channels and to dilate the cerebral arteries. (PMID: 16258232) [HMDB] (5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoate (5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoic acid (all-Z)-20-hydroxy-5,8,11,14-eicosatetraenoate (all-Z)-20-hydroxy-5,8,11,14-eicosatetraenoic acid 20-HETE 20-Hydroxy arachidonate 20-Hydroxy arachidonic acid 20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate 20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid 20-Hydroxy-5,8,11,14-eicosatetraenoate 20-Hydroxy-5,8,11,14-eicosatetraenoic acid 20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoate 20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 20-Hydroxyarachidonate 20-Hydroxyarachidonic acid 20-Hydroxyeicosatetraenoate 20-Hydroxyicosatetraenoate 20-Hydroxyicosatetraenoic acid C20H32O3 320.4663 320.23514489 20-hydroxyicosa-5,8,11,14-tetraenoic acid 20-hydroxyarachidonic acid 79551-86-3 OCCCCCC=CCC=CCC=CCC=CCCCC(O)=O InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23) NNDIXBJHNLFJJP-UHFFFAOYSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Monocarboxylic acids and derivatives Organic oxides Primary alcohols Straight chain fatty acids Unsaturated fatty acids Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Hydroxy fatty acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Primary alcohol Straight chain fatty acid Unsaturated fatty acid Solid logp 5.87 ALOGPS logs -5.43 ALOGPS solubility 1.19e-03 g/l ALOGPS logp 5.15 ChemAxon pka_strongest_acidic 4.82 ChemAxon pka_strongest_basic -2 ChemAxon iupac 20-hydroxyicosa-5,8,11,14-tetraenoic acid ChemAxon average_mass 320.4663 ChemAxon mono_mass 320.23514489 ChemAxon smiles OCCCCCC=CCC=CCC=CCC=CCCCC(O)=O ChemAxon formula C20H32O3 ChemAxon inchi InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23) ChemAxon inchikey NNDIXBJHNLFJJP-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 101.88 ChemAxon polarizability 39.01 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 Specdb::CMs 107831 Specdb::CMs 120273 Specdb::CMs 826139 Specdb::CMs 826140 Specdb::CMs 826141 Specdb::CMs 826142 Specdb::CMs 826143 Specdb::CMs 826144 Specdb::MsMs 3408163 Specdb::MsMs 3408164 Specdb::MsMs 3408165 Specdb::MsMs 3409254 Specdb::MsMs 3409255 Specdb::MsMs 3409256 HMDB05998 34306 #<Reference:0x000055ce32ce9680> 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