1.02011-09-21 00:28:26 UTC2015-07-21 06:57:39 UTCFDB0233466-Ketoprostaglandin E16-Ketoprostaglandin E1(6-keto PGE1) is a biologically active and stable prostacyclin (PGI2) metabolite and a substrate for Adenylate cyclase type III. 6-keto PGE1 is a potent coronary vasodilator. 6-keto PGE1 could be elevated in plasma of patients with primary thrombocythaemia. 6-keto-PGE1 has approximately four times less potent antiplatelet activity than PGI2 on a molar basis in man. The cardiovascular and plasma renin activity (PRA) changes are less prominent for 6-keto-PGE1 than PGI2. Salt loading slightly increases urinary 6-keto PGE1.
6-keto-PGE1 elicits the same biological effects as PGI2 in human platelets and in rabbit aorta and mesenteric artery, being, however, less potent. 6-keto-PGE1 dose-dependently stimulates adenylate cyclase activity in membranes of human platelets and cultured myocytes from rabbit aorta and mesenteric artery. The extent of stimulation of the enzyme by 6-keto-PGE1 is the same as elicited by PGI2, while the apparent affinity is lower than that of prostacyclin, both in platelets and in vascular smooth muscle cells. At the level of platelet membranes, 6-keto-PGE1 interacts with the binding sites labelled by PGI2. However, in platelets as well as in mesenteric artery myocytes, 6-keto-PGE1 interacts with only one class of sites as demonstrated either by binding or by adenylate cyclase studies, whereas PGI2 in the same conditions recognizes two different classes. (PMID: 3186779, 3075239, 3472253, 3912001, 3881881, 6391491)
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]6-keto PGE16-Keto-PGE16-keto-Prostaglandin e16-ketoprostaglandin E16-KPGE16-Oxo-PGE16-oxo-prostaglandin E16-Oxoprostaglandin E16,9-dioxo-11R,15S-dihydroxy-13E-prostenoate6,9-dioxo-11R,15S-dihydroxy-13E-prostenoic acidC20H32O6368.4645368.2198887567-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-6-oxoheptanoic acid6-Keto-PGE167786-53-2CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CC(=O)CCCCC(O)=OInChI=1S/C20H32O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-18,21,23H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+/m0/s1ROUDCKODIMKLNO-CTBSXBMHSA-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 alcohols and derivativesCyclic ketonesCyclopentanolsFatty alcoholsHydrocarbon derivativesHydroxy fatty acidsKeto fatty acidsLong-chain fatty acidsMonocarboxylic acids and derivativesOrganic oxidesAlcoholAliphatic homomonocyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeCyclic alcoholCyclic ketoneCyclopentanolFatty alcoholHydrocarbon derivativeHydroxy fatty acidKeto fatty acidKetoneLong-chain fatty acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundProstaglandin skeletonSecondary alcoholProstaglandinsProstaglandinsprostaglandins ESolidlogp2.02logs-3.32solubility1.76e-01 g/llogp2.41pka_strongest_acidic4.1pka_strongest_basic-1.6iupac7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-6-oxoheptanoic acidaverage_mass368.4645mono_mass368.219888756smilesCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CC(=O)CCCCC(O)=OformulaC20H32O6inchiInChI=1S/C20H32O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-18,21,23H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+/m0/s1inchikeyROUDCKODIMKLNO-CTBSXBMHSA-Npolar_surface_area111.9refractivity98.96polarizability42.05rotatable_bond_count13acceptor_count6donor_count3physiological_charge-1formal_charge0Arachidonic Acid MetabolismSMP00075map00590Specdb::CMs2144Specdb::CMs2180Specdb::CMs25624Specdb::CMs31517Specdb::CMs31518Specdb::CMs38742Specdb::CMs175284Specdb::MsMs322771Specdb::MsMs322772Specdb::MsMs322773Specdb::MsMs370768Specdb::MsMs370769Specdb::MsMs370770Specdb::MsMs2269186Specdb::MsMs2269187Specdb::MsMs2269188Specdb::MsMs3073233Specdb::MsMs3073234Specdb::MsMs3073235HMDB0424128269#<Reference:0x0000555675070e10>#<Reference:0x0000555675070be0>#<Reference:0x0000555675070a28>#<Reference:0x0000555675070870>#<Reference:0x0000555675070668>#<Reference:0x00005556750704b0>#<Reference:0x0000555675070280>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