1.02011-09-21 00:28:23 UTC2015-07-21 06:57:39 UTCFDB023342Prostaglandin B2Prostaglandin B2 (PGB2) is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207)
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]PGB2C20H30O4334.4498334.2144094487-{2-[(3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid7-{2-[(3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid13367-85-6[H][C@@](O)(CCCCC)C=CC1=C(CC=CCCCC(O)=O)C(=O)CC1InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12,14,17,21H,2-3,5-6,8-11,13,15H2,1H3,(H,23,24)/t17-/m1/s1PRFXRIUZNKLRHM-QGZVFWFLSA-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 compoundsCarboxylic acidsCyclic ketonesHydrocarbon derivativesHydroxy fatty acidsLong-chain fatty acidsMonocarboxylic acids and derivativesOrganic oxidesSecondary alcoholsUnsaturated fatty acidsAlcoholAliphatic homomonocyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeCyclic ketoneFatty acidHydrocarbon derivativeHydroxy fatty acidKetoneLong-chain fatty acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundProstaglandin skeletonSecondary alcoholUnsaturated fatty acidSolidlogp4.07logs-4.05solubility2.99e-02 g/llogp4.18pka_strongest_acidic4.25pka_strongest_basic-1.6iupac7-{2-[(3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acidaverage_mass334.4498mono_mass334.214409448smiles[H][C@@](O)(CCCCC)C=CC1=C(CC=CCCCC(O)=O)C(=O)CC1formulaC20H30O4inchiInChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12,14,17,21H,2-3,5-6,8-11,13,15H2,1H3,(H,23,24)/t17-/m1/s1inchikeyPRFXRIUZNKLRHM-QGZVFWFLSA-Npolar_surface_area74.6refractivity98.61polarizability39.8rotatable_bond_count12acceptor_count4donor_count2physiological_charge-1formal_charge0Arachidonic Acid MetabolismSMP00075map00590HMDB0423628099E2P#<Reference:0x0000555675dcaf20>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