1.0 2011-09-21 00:26:48 UTC 2015-07-21 06:57:36 UTC FDB023242 15(S)-HETE 15(S)-HETE is a hydroxyeicosatetraenoic acid. Hydroxyeicosatetraenoic acids (HETEs) are formed by the 5-, 12- and 15-lipoxygenase (LO) pathways. 5- and 12-LO products are mainly proinflammatory in the skin whereas the main 15-LO product 15-HETE has antiinflammatory capacities. In vitro 15-HETE has been shown to inhibit LTB4 formation, 12-HETE formation and specifically inhibits the neutrophil chemotactic effect of LTB4. The inhibition of LTB4 formation is probably due to modulation of the 5-LO because no changes in PGE2 formation have been determined. In vivo, 15-HETE inhibits LTB4-induced erythema and edema, and reduces LTB4 in the synovial fluid of carragheenan-induced experimental arthritis in dogs. 15-HETE has also some immunomodulatory effects. It inhibits the mixed lymphocyte reaction, induces generation of murine cytotoxic suppressor T cells, and it decreases interferon production by murine lymphoma cells. Furthermore, IL-4 and IL-13 have recently been shown to be potent activators of the 15-LO in mononuclear cells. (PMID: 11104340) [HMDB] (15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoate (15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoic acid (15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoate (15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acid (15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosic acid (15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoate (15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoic acid (15S)-Hydroxy-(5Z,8Z,11Z,13e)-eicosatetraenoate (15S)-Hydroxy-(5Z,8Z,11Z,13e)-eicosatetraenoic acid (15S)-Hydroxyeicosa-(5Z,8Z,11Z,13e)-tetraenoate (15S)-Hydroxyeicosa-(5Z,8Z,11Z,13e)-tetraenoic acid (5Z,8Z,11Z,13e,15S)-15-Hydroxy-5,8,11,13-eicosatetraenoate (5Z,8Z,11Z,13e,15S)-15-Hydroxy-5,8,11,13-eicosatetraenoic acid (5Z,8Z,11Z,13e,15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoate (5Z,8Z,11Z,13e,15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoic acid (5Z,8Z,11Z,13E)-(15S)-15-Hydroxyicosa-5,8,11,13-tetraenoate (5Z,8Z,11Z,13E)-(15S)-15-Hydroxyicosa-5,8,11,13-tetraenoic acid (S)-15-HETE 15 Hete 15-HETE 15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate 15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid 15(S)-Hydroxyeicosatetraenoate 15(S)-Hydroxyeicosatetraenoic acid 15S-HETE 15S-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoate 15S-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid Icomucret C20H32O3 320.4663 320.23514489 (15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid (15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid 54845-95-3 [H][C@](O)(CCCCC)C=CC=CCC=CCC=CCCCC(O)=O InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/t19-/m0/s1 JSFATNQSLKRBCI-IBGZPJMESA-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 5.82 ALOGPS logs -5.22 ALOGPS solubility 1.95e-03 g/l ALOGPS logp 5.36 ChemAxon pka_strongest_acidic 4.82 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid ChemAxon average_mass 320.4663 ChemAxon mono_mass 320.23514489 ChemAxon smiles [H][C@](O)(CCCCC)C=CC=CCC=CCC=CCCCC(O)=O ChemAxon formula C20H32O3 ChemAxon inchi InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/t19-/m0/s1 ChemAxon inchikey JSFATNQSLKRBCI-IBGZPJMESA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 101.47 ChemAxon polarizability 38.76 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 HMDB03876 15558 #<Reference:0x000055ce31bd1410> 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