1.0 2011-09-21 01:23:18 UTC 2015-07-21 06:59:05 UTC FDB027364 15-HEPE 15-HEPE has been identified as a possible anti-inflammatory metabolite, and its elevated presence in the epidermis of animals fed oils rich in 20:5(n-3) or 18:3(n-6) may provide a mechanism for the beneficial effects of these oils on inflammatory conditions. 15-HEPE is a metabolite of eicosapentaenoic acid (EPA) which has anti-inflammatory properties and plays an important role in the resolution phase of inflammation. 15-HEPE is deposited in the epidermis, particularly in the metabolically active basal layer. This is considered advantageous in psoriasis therapy. (PMID: 17540633, 2106017) [HMDB] (15R)-15-hydroxyeicosa-5Z,8Z,11Z,13E,17Z-pentaenoate (15R)-15-hydroxyeicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acid (15S)-15-hydroxyeicosa-5Z,8Z,11Z,13E,17Z-pentaenoate (15S)-15-hydroxyeicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acid 15-Hydroxy-5,8,11,13,17-eicosapentaenoate 15-Hydroxy-5,8,11,13,17-eicosapentaenoic acid 15-Hydroxyeicosapentaenoate 15-Hydroxyeicosapentaenoic acid 15(R)-HEPE 15(S)-HEPE C20H30O3 318.4504 318.219494826 16-hydroxyicosa-5,8,11,13,17-pentaenoic acid 16-hydroxyicosa-5,8,11,13,17-pentaenoic acid 97850-14-1 CCC=CC(O)CC=CC=CCC=CCC=CCCCC(O)=O InChI=1S/C20H30O3/c1-2-3-16-19(21)17-14-12-10-8-6-4-5-7-9-11-13-15-18-20(22)23/h3-5,8-12,14,16,19,21H,2,6-7,13,15,17-18H2,1H3,(H,22,23) UDXLGBLAJBYLSZ-UHFFFAOYSA-N belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds. Hydroxyeicosapentaenoic 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 Hydroxyeicosapentaenoic acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Solid logp 5.55 ALOGPS logs -5.03 ALOGPS solubility 2.96e-03 g/l ALOGPS logp 4.99 ChemAxon pka_strongest_acidic 4.82 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 16-hydroxyicosa-5,8,11,13,17-pentaenoic acid ChemAxon average_mass 318.4504 ChemAxon mono_mass 318.219494826 ChemAxon smiles CCC=CC(O)CC=CC=CCC=CCC=CCCCC(O)=O ChemAxon formula C20H30O3 ChemAxon inchi InChI=1S/C20H30O3/c1-2-3-16-19(21)17-14-12-10-8-6-4-5-7-9-11-13-15-18-20(22)23/h3-5,8-12,14,16,19,21H,2,6-7,13,15,17-18H2,1H3,(H,22,23) ChemAxon inchikey UDXLGBLAJBYLSZ-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 102.59 ChemAxon polarizability 38.23 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB10209 #<Reference:0x000055ce30bf6068> #<Reference:0x000055ce30bf5d98> 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