1.0 2011-09-21 00:29:29 UTC 2015-07-21 06:57:41 UTC FDB023408 12(R)-HPETE 12(R)-HPETE is a hydroperoxyeicosatetraenoic acid eicosanoid derived from arachidonic acid. The epidermal lipoxygenases 12R-LOX and eLOX3 act in sequence to convert arachidonic acid via 12(R)-HPETE to 12(R)-HETE and the corresponding epoxyalcohol, 8(R)-hydroxy-11(R),12(R)-epoxyeicosatrienoic acid. The epidermal lipoxygenases 12R-LOX and eLOX3 are the gene products of ALOX12B and ALOXE3. Mutations in ALOXE3 or ALOX12B have been found in families with autosomal-recessive congenital ichthyosis (ARCI). ARCI is a clinically and genetically heterogeneous group of severe hereditary keratinization disorders characterized by intense scaling of the whole integument, and differences in color and shape, often associated with erythema. Mutations in ALOXE3 and ALOX12B on chromosome 17p13, which code for two different epidermal lipoxygenases, were found in patients with ichthyosiform erythroderma. Genetic studies indicated that 12R-lipoxygenase (12R-LOX) or epidermal lipoxygenase-3 (eLOX3) was mutated in six families affected by non-bullous congenital ichthyosiform erythroderma (NCIE), one of the main clinical forms of ichthyosis. (PMID: 16116617, 15629692) [HMDB] (5Z,8Z,10e,14Z)-(12R)-12-Hydroperoxyeicosa-5,8,10,14-tetraenoate (5Z,8Z,10e,14Z)-(12R)-12-Hydroperoxyeicosa-5,8,10,14-tetraenoic acid (5Z,8Z,10e,14Z)-(12R)-12-Hydroperoxyicosa-5,8,10,14-tetraenoate (5Z,8Z,10e,14Z)-(12R)-12-Hydroperoxyicosa-5,8,10,14-tetraenoic acid 12R-HpETE 12R-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoate 12R-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid 12R-hydroperoxyeicosatetraenoate 12R-hydroperoxyeicosatetraenoic acid C20H32O4 336.4657 336.230059512 (12R)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid (12R)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid 126873-49-2 [H][C@](CC=CCCCCC)(OO)C=CC=CCC=CCCCC(O)=O InChI=1S/C20H32O4/c1-2-3-4-5-10-13-16-19(24-23)17-14-11-8-6-7-9-12-15-18-20(21)22/h7-11,13-14,17,19,23H,2-6,12,15-16,18H2,1H3,(H,21,22)/t19-/m1/s1 ZIOZYRSDNLNNNJ-LJQANCHMSA-N belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds. Hydroperoxyeicosatetraenoic acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic acyclic compounds Alkyl hydroperoxides Allylic hydroperoxides Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroperoxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Peroxols Unsaturated fatty acids Aliphatic acyclic compound Alkyl hydroperoxide Allylic hydroperoxide Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroperoxide Hydroperoxy fatty acid Hydroperoxyeicosatetraenoic acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Peroxol Unsaturated fatty acid Solid logp 5.90 ALOGPS logs -5.30 ALOGPS solubility 1.69e-03 g/l ALOGPS logp 5.81 ChemAxon pka_strongest_acidic 4.89 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (12R)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid ChemAxon average_mass 336.4657 ChemAxon mono_mass 336.230059512 ChemAxon smiles [H][C@](CC=CCCCCC)(OO)C=CC=CCC=CCCCC(O)=O ChemAxon formula C20H32O4 ChemAxon inchi InChI=1S/C20H32O4/c1-2-3-4-5-10-13-16-19(24-23)17-14-11-8-6-7-9-12-15-18-20(21)22/h7-11,13-14,17,19,23H,2-6,12,15-16,18H2,1H3,(H,21,22)/t19-/m1/s1 ChemAxon inchikey ZIOZYRSDNLNNNJ-LJQANCHMSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 102.82 ChemAxon polarizability 41.14 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 HMDB04692 34145 #<Reference:0x00007f093c0334b8> #<Reference:0x00007f093c033300> 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