1.0 2011-09-21 00:29:25 UTC 2015-07-21 06:57:41 UTC FDB023404 13,14-Dihydro-15-keto PGF2a 13,14-dihydro-15-keto PGF2a E1 is an isoprostane. The isoprostanes embody a vast family of novel prostaglandin-like lipids that are produced by nonenzymatic peroxidation of arachidonic acid (AA) in response to free radicals and reactive oxygen species. Although free AA is required for the formation of prostaglandins by cyclooxygenases, the isoprostanes can be generated nonenzymatically from esterified AA in membrane phospholipids before being released by a phospholipase(s). Another dissimilarity is that isoprostanes feature side chains that are almost exclusively orientated cis relative to the cyclopentane ring and are therefore distinct from the prostaglandins, which always have side chains in the trans configuration. Nevertheless, isoprostanes are isomeric with prostaglandins and have been given the prefix D-, E-, and F{alpha}- to denote the prostane ring shared with PGD2, PGE2, and PGF2{alpha} respectively. An additional level of complexity is that peroxidation of AA can occur at one of any of four carbon atoms producing regioisomers, the so-called 5-, 12-, 8-, and 15-series isoprostanes, each consisting of eight racemic diastereomers. Thus, a total of 64 isomers can be generated for each of the D-, E-, and F{alpha}-ring isoprostanes. (PMID: 15528403) Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. [HMDB] 13,14-dihydro-15-keto PGF2alpha 13,14-dihydro-15-keto-Pgf2a 13,14-Dihydro-15-keto-pgf2alpha 13,14-dihydro-15-keto-Pgf2α 13,14-dihydro-15-keto-Prostaglandin F2a 13,14-Dihydro-15-ketoprostaglandin F 13,14-dihydro-15-Ketoprostaglandin F2a 13,14-dihydro-15-Ketoprostaglandin F2alpha 13,14-dihydro-15-Ketoprostaglandin F2α 13,14-Dihydro-15-oxoprostaglandin F 15-keto-13,14-dihydro-Pgf2a 15-Keto-13,14-dihydro-pgf2alpha 15-keto-13,14-dihydro-Pgf2α 15-keto-13,14-Dihydroprostaglandin F2-a 15-keto-13,14-Dihydroprostaglandin F2-alpha 15-keto-13,14-Dihydroprostaglandin F2-α 15-keto-13,14-Dihydroprostaglandin F2a 15-Keto-13,14-dihydroprostaglandin F2alpha 15-keto-13,14-Dihydroprostaglandin F2α 9S,11S-Dihydroxy-15-oxo-5Z-prostenoate 9S,11S-Dihydroxy-15-oxo-5Z-prostenoic acid Dhk-pgf2a Dhk-pgf2alpha Dhk-pgf2α PGFM C20H34O5 354.481 354.240624198 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid 27376-76-7 [H][C@@]1(O)C[C@]([H])(O)[C@]([H])(CC=CCCCC(O)=O)[C@@]1([H])CCC(=O)CCCCC InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,16-19,22-23H,2-3,5-6,8-14H2,1H3,(H,24,25)/t16-,17-,18+,19-/m1/s1 VKTIONYPMSCHQI-AKHDSKFASA-N belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Prostaglandins and related compounds Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic homomonocyclic compounds Carboxylic acids Cyclic alcohols and derivatives Cyclopentanols Hydrocarbon derivatives Hydroxy fatty acids Ketones Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Unsaturated fatty acids Alcohol Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclopentanol Fatty acid Hydrocarbon derivative Hydroxy fatty acid Ketone Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Prostaglandin skeleton Secondary alcohol Unsaturated fatty acid Solid logp 3.12 ALOGPS logs -3.52 ALOGPS solubility 1.07e-01 g/l ALOGPS logp 3.02 ChemAxon pka_strongest_acidic 4.31 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid ChemAxon average_mass 354.481 ChemAxon mono_mass 354.240624198 ChemAxon smiles [H][C@@]1(O)C[C@]([H])(O)[C@]([H])(CC=CCCCC(O)=O)[C@@]1([H])CCC(=O)CCCCC ChemAxon formula C20H34O5 ChemAxon inchi InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,16-19,22-23H,2-3,5-6,8-14H2,1H3,(H,24,25)/t16-,17-,18+,19-/m1/s1 ChemAxon inchikey VKTIONYPMSCHQI-AKHDSKFASA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 98.48 ChemAxon polarizability 41.39 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB04685 #<Reference:0x000055ce332bb180> 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