1.0 2011-09-21 00:37:48 UTC 2015-07-21 06:57:57 UTC FDB023973 8-iso-13,14-dihydro-15-keto-PGF2a 8-iso-13,14-dihydro-15-keto-PGF2a is an isoprostane. Isoprostanes are a family of prostaglandin (PG) isomers generated by free radical-catalysed peroxidation and then rearrangement of arachidonic acid. In addition, isoprostanes can be produced by cyclo-oxygenase (COX) dependent pathways. Several cell types have been shown to release increased levels of the F2 isoprostane, 8-iso PGF2alpha, when stimulated with inflammatory mediators or subjected to oxidative stress in vitro. Furthermore, 8-iso PGF2alpha levels are elevated in rats in vivo when prooxidant conditions are induced experimentally. Similarly, elevated isoprostane production has been demonstrated in clinical conditions characterized by oxidant stress including diabetes, alcoholism, paraquat poisoning, myocardial reperfusion, critical illness, pre-eclampsia and smoking. Consequently, the measurement of 8-iso PGF2alpha in plasma and urine has been proposed as a relevant and convenient method to monitor oxidant stress in man. (PMID: 11309241) [HMDB] (5Z,8b,9a,11a)-9,11-dihydroxy-15-oxo-Prost-5-en-1-oate (5Z,8b,9a,11a)-9,11-dihydroxy-15-oxo-Prost-5-en-1-oic acid 9S,11R-dihydroxy-15-oxo-5Z-prostaenoate 9S,11R-dihydroxy-15-oxo-5Z-prostaenoic acid 9S,11R-dihydroxy-15-oxo-5Z-prostaenoic acid-cyclo[8S,12R] C20H34O5 354.481 354.240624198 7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid 7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid 191919-02-5 [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+/m0/s1 VKTIONYPMSCHQI-ZSYWTGECSA-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-[(1S,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+/m0/s1 ChemAxon inchikey VKTIONYPMSCHQI-ZSYWTGECSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 98.48 ChemAxon polarizability 41.76 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB06562 #<Reference:0x000055ce304931b8> 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