1.0 2011-09-21 00:17:23 UTC 2015-07-21 06:57:17 UTC FDB022647 Prostaglandin F2b Prostaglandin F2b is a naturally occurring isoprostane. Isoprostanes are arachidonic acid metabolites produced by peroxidative attack of membrane lipids. These accumulate to substantial levels in many clinical conditions characterized in part by accumulation of free radicals and reactive oxygen species, including asthma, hypertension and ischemia-reperfusion injury. For this reason, they are frequently used as markers of oxidative stress; however, many are now finding that these molecules are not inert, but in fact evoke powerful biological responses in an increasing array of cell types. In many cases, these biological effects can account in part for the various features and manifestations of those clinical conditions. Thus, it may be possible that the isoprostanes are playing somewhat of a causal role in those disease states. Lipid-peroxidation forms primary- or secondary-end products like conjugated dienes, lipid hydroperoxides, gaseous alkanes, and prostaglandin F2-like products. They are created as major products by free-radical catalyzed peroxidation of esterified arachidonic acid (AA) in membrane phospholipids. They are also minor products of the activity of platelet cyclooxygenase-1 (COX-1) in response to stimuli such as collagen, thrombin, or arachidonate. The levels of Prostaglandin F2b and F2-isoprostanes in CSF and urine are elevated in Alzheimer's disease (AD) patients when compared to that of age-matched controls. (PMID: 15275956, 14504139) 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] (5Z,13E)-9,11,15-trihydroxy-prosta-5,13-dien-1-oate (5Z,13E)-9,11,15-trihydroxy-prosta-5,13-dien-1-oic acid 5-Heptenoate, 7-[3,5-dihydroxy-2(3-hydroxy-1-octenyl)cyclopentyl]-, stereoisomer 5-Heptenoic acid, 7-[3,5-dihydroxy-2(3-hydroxy-1-octenyl)cyclopentyl]-, stereoisomer 7-[3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-Heptenoic acid stereoisomer 7-[3a,5b-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoate 7-[3a,5b-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid 9b,11a-PGF2 9b,11a-PGF2a 9beta,11alpha-PGF2a 9beta,11alpha-PGF2alpha 9β,11α-pgf2a 9β,11α-pgf2α PGF2b PGF2beta PGF2β Prostaglandin F2-b Prostaglandin F2-beta Prostaglandin F2-β Prostaglandin F2beta Prostaglandin F2β C20H34O5 354.481 354.240624198 7-[(1R,2R,3R,5R)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid 7-[(1R,2R,3R,5R)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid 4510-16-1 [H]C(=C[C@@]1([H])[C@]([H])(O)C[C@@]([H])(O)[C@]1([H])CC=CCCCC(O)=O)[C@@]([H])(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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t15-,16+,17+,18+,19+/m0/s1 PXGPLTODNUVGFL-UURKPOQGSA-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 Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Cyclopentanols Hydrocarbon derivatives Hydroxy fatty acids 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 Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Prostaglandin skeleton Secondary alcohol Unsaturated fatty acid Solid logp 3.11 ALOGPS logs -3.48 ALOGPS solubility 1.17e-01 g/l ALOGPS logp 2.61 ChemAxon pka_strongest_acidic 4.36 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 7-[(1R,2R,3R,5R)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid ChemAxon average_mass 354.481 ChemAxon mono_mass 354.240624198 ChemAxon smiles [H]C(=C[C@@]1([H])[C@]([H])(O)C[C@@]([H])(O)[C@]1([H])CC=CCCCC(O)=O)[C@@]([H])(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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t15-,16+,17+,18+,19+/m0/s1 ChemAxon inchikey PXGPLTODNUVGFL-UURKPOQGSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 100.47 ChemAxon polarizability 41.01 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB01483 28922 #<Reference:0x000055ce30fceb90> #<Reference:0x000055ce30fce9b0> 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