1.0 2011-09-21 00:32:29 UTC 2015-07-21 06:57:47 UTC FDB023618 8-iso-15-keto-PGF2a 8-iso-15-keto-PGF2alpha is an isoprostane. Isoprostanes are produced during peroxidation of membrane lipids by free radicals and reactive oxygen species, and are currently used as markers of many disease states and experimental conditions in which oxidative stress is a prominent feature. A small number of reports have described the ability of some isoprostanes to evoke important biological effects in smooth muscle and other cell types. There is a long (and growing) list of disease states and pathophysiological conditions which are associated with marked elevation in the levels of iso- prostanes. For example, measured levels of the plasma, urine, bronchoalveolar lavage fluid, and/or tissues of smokers, patients with asthma chronic obstructive pulmonary disease, interstitial lung disease, cystic fibrosis, or acute chest syndrome, during exposure to allergen, ozone or hyperoxia; and during ventilated ischemia. Likewise, cardiovascular conditions such as renal, myocardial, ischemia-reperfusion injury, atherosclerosis, and pre-eclampsia are also indicated by a marked elevation of plasma/urinary levels of isoprostanes. (PMID: 10930353) [HMDB] (5Z,8b,9a,11a,13E)-9,11-dihydroxy-15-oxo-Prosta-5,13-dien-1-oate (5Z,8b,9a,11a,13E)-9,11-dihydroxy-15-oxo-Prosta-5,13-dien-1-oic acid 8-iso-15-keto-PGF2alpha 9S,11R-dihydroxy-15-oxo-5Z,13E-prostadienoic acid-cyclo[8S,12R] C20H32O5 352.4651 352.224974134 7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooct-1-en-1-yl)cyclopentyl]hept-5-enoic acid 7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooct-1-en-1-yl)cyclopentyl]hept-5-enoic acid 191919-01-4 [H][C@]1(O)C[C@@]([H])(O)[C@]([H])(C=CC(=O)CCCCC)[C@]1([H])CC=CCCCC(O)=O InChI=1S/C20H32O5/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/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t16-,17+,18-,19+/m0/s1 LOLJEILMPWPILA-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 Acryloyl compounds Carboxylic acids Cyclic alcohols and derivatives Cyclopentanols Enones Hydrocarbon derivatives Hydroxy fatty acids Ketones Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Unsaturated fatty acids Acryloyl-group Alcohol Aliphatic homomonocyclic compound Alpha,beta-unsaturated ketone Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclopentanol Enone 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 3.03 ALOGPS logs -3.58 ALOGPS solubility 9.33e-02 g/l ALOGPS logp 3.02 ChemAxon pka_strongest_acidic 4.36 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac 7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooct-1-en-1-yl)cyclopentyl]hept-5-enoic acid ChemAxon average_mass 352.4651 ChemAxon mono_mass 352.224974134 ChemAxon smiles [H][C@]1(O)C[C@@]([H])(O)[C@]([H])(C=CC(=O)CCCCC)[C@]1([H])CC=CCCCC(O)=O ChemAxon formula C20H32O5 ChemAxon inchi InChI=1S/C20H32O5/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/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t16-,17+,18-,19+/m0/s1 ChemAxon inchikey LOLJEILMPWPILA-ZSYWTGECSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 99.57 ChemAxon polarizability 40.53 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB05077 #<Reference:0x000055ce318a0070> 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