1.0 2011-09-21 00:29:22 UTC 2017-04-03 04:53:11 UTC FDB023401 16(R)-HETE 16(R)-HETE is a metabolite of arachidonic acid, metabolized by the enzyme Cytochrome P450, family 2, subfamily C [EC:1.14.13.80 1.14.13.48 1.14.13.49]. 16(R)-HETE is an endogenous lipidic inhibitor of human neutrophil inhibitor of adhesion and aggregation activity. Human polymorphonuclear leukocytes (PMNs) produce 16(R)-HETE that modulates their function. HETEs have different biological properties based on sites of production and can be stored in tissue lipids and released in response to hormonal stimuli. Eicosanoids generated during the actions of growth factors and vasoconstrictors can modulate disease processes by affecting vascular homeostasis, inflammation, cellular growth, apoptosis and oxidant stress. In lung, the presence of these eicosanoids in the pulmonary vasculature and airways, including effects on pulmonary vascular and bronchial smooth muscle tone and airway epithelial ion transport. (PMID: 16258232, 14626496, 12681244, 11123211, 14552765, 11126912) [HMDB] (16R,5Z,8Z,11Z,14Z)-16-Hydroxy-5,8,11,14-eicosatetraenoate (16R,5Z,8Z,11Z,14Z)-16-Hydroxy-5,8,11,14-eicosatetraenoic acid (5Z,8Z,11Z,14Z,16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoate (5Z,8Z,11Z,14Z,16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoic acid (5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoate (5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoic acid (5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyicosa-5,8,11,14-tetraenoate (5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyicosa-5,8,11,14-tetraenoic acid (all-cis)-16(R)-Hydroxy-5,8,11,14-eicosatetraenoate (all-cis)-16(R)-Hydroxy-5,8,11,14-eicosatetraenoic acid (all-Z)-16(R)-Hydroxy-5,8,11,14-eicosatetraenoate (all-Z)-16(R)-Hydroxy-5,8,11,14-eicosatetraenoic acid 16-HETE 16(R)-Hydroxy-all-cis-5,8,11,14-eicosatetraenoate 16(R)-Hydroxy-all-cis-5,8,11,14-eicosatetraenoic acid 16(R)-Hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate 16(R)-Hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid 16R-HETE 16R-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoate 16R-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid C20H32O3 320.4663 320.23514489 (16R)-16-hydroxyicosa-5,8,11,14-tetraenoic acid (16R)-16-hydroxyicosa-5,8,11,14-tetraenoic acid 128914-46-5 [H][C@@](O)(CCCC)C=CCC=CCC=CCC=CCCCC(O)=O InChI=1S/C20H32O3/c1-2-3-16-19(21)17-14-12-10-8-6-4-5-7-9-11-13-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/t19-/m1/s1 JEKNPVYFNMZRJG-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 5.77 ALOGPS logs -5.21 ALOGPS solubility 1.98e-03 g/l ALOGPS logp 5.36 ChemAxon pka_strongest_acidic 4.82 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (16R)-16-hydroxyicosa-5,8,11,14-tetraenoic acid ChemAxon average_mass 320.4663 ChemAxon mono_mass 320.23514489 ChemAxon smiles [H][C@@](O)(CCCC)C=CCC=CCC=CCC=CCCCC(O)=O ChemAxon formula C20H32O3 ChemAxon inchi InChI=1S/C20H32O3/c1-2-3-16-19(21)17-14-12-10-8-6-4-5-7-9-11-13-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/t19-/m1/s1 ChemAxon inchikey JEKNPVYFNMZRJG-LJQANCHMSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 101.47 ChemAxon polarizability 39.68 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 HMDB04680 34162 #<Reference:0x000055ce30b75558> #<Reference:0x000055ce30b75328> #<Reference:0x000055ce30b75120> #<Reference:0x000055ce30b74ef0> #<Reference:0x000055ce30b74ce8> #<Reference:0x000055ce30b74b08> 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 Cytochrome P450 2D6 Q6NWU0 CYP2D6 Cytochrome P450, family 1, subfamily A, polypeptide 1 A0N0X8 CYP1A1