1.02011-09-21 00:20:34 UTC2015-07-21 06:57:24 UTCFDB0228518-isoprostaglandin PGF2b8-isoprostaglandin PGF2beta is an 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. (PMID: 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]8-iso-PGF2b8-iso-PGF2beta8-isoprostaglandin PGF2beta9R,11R,15S-trihydroxy-5Z,13E-prostadienoate9R,11R,15S-trihydroxy-5Z,13E-prostadienoic acid9R,11R,15S-trihydroxy-5Z,13E-prostadienoic acid-cyclo[8S,12R]C20H34O5354.481354.2406241987-[(1S,2R,3R,5R)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid7-[(1S,2R,3R,5R)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid177020-26-7[H]C(=C[C@@]1([H])[C@]([H])(O)C[C@@]([H])(O)[C@@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CCCCCInChI=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/s1PXGPLTODNUVGFL-NTZUZEMLSA-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 compoundsOrganic compoundsLipids and lipid-like moleculesFatty AcylsEicosanoidsAliphatic homomonocyclic compoundsCarbonyl compoundsCarboxylic acidsCyclic alcohols and derivativesCyclopentanolsHydrocarbon derivativesHydroxy fatty acidsLong-chain fatty acidsMonocarboxylic acids and derivativesOrganic oxidesUnsaturated fatty acidsAlcoholAliphatic homomonocyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeCyclic alcoholCyclopentanolFatty acidHydrocarbon derivativeHydroxy fatty acidLong-chain fatty acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundProstaglandin skeletonSecondary alcoholUnsaturated fatty acidSolidlogp3.11logs-3.48solubility1.17e-01 g/llogp2.61pka_strongest_acidic4.36pka_strongest_basic-1.6iupac7-[(1S,2R,3R,5R)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acidaverage_mass354.481mono_mass354.240624198smiles[H]C(=C[C@@]1([H])[C@]([H])(O)C[C@@]([H])(O)[C@@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CCCCCformulaC20H34O5inchiInChI=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/s1inchikeyPXGPLTODNUVGFL-NTZUZEMLSA-Npolar_surface_area97.99refractivity100.47polarizability41.49rotatable_bond_count12acceptor_count5donor_count4physiological_charge-1formal_charge0HMDB02115#<Reference:0x00005556755cdd68>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823