1.0 2011-09-21 00:28:26 UTC 2015-07-21 06:57:39 UTC FDB023346 6-Ketoprostaglandin E1 6-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 PGE1 6-Keto-PGE1 6-keto-Prostaglandin e1 6-ketoprostaglandin E1 6-KPGE1 6-Oxo-PGE1 6-oxo-prostaglandin E1 6-Oxoprostaglandin E1 6,9-dioxo-11R,15S-dihydroxy-13E-prostenoate 6,9-dioxo-11R,15S-dihydroxy-13E-prostenoic acid C20H32O6 368.4645 368.219888756 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-6-oxoheptanoic acid 6-Keto-PGE1 67786-53-2 CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CC(=O)CCCCC(O)=O InChI=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/s1 ROUDCKODIMKLNO-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 compounds Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic homomonocyclic compounds Carboxylic acids Cyclic alcohols and derivatives Cyclic ketones Cyclopentanols Fatty alcohols Hydrocarbon derivatives Hydroxy fatty acids Keto fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Alcohol Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclic ketone Cyclopentanol Fatty alcohol Hydrocarbon derivative Hydroxy fatty acid Keto fatty acid Ketone Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Prostaglandin skeleton Secondary alcohol Prostaglandins Prostaglandins prostaglandins E Solid logp 2.02 ALOGPS logs -3.32 ALOGPS solubility 1.76e-01 g/l ALOGPS logp 2.41 ChemAxon pka_strongest_acidic 4.1 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-6-oxoheptanoic acid ChemAxon average_mass 368.4645 ChemAxon mono_mass 368.219888756 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CC(=O)CCCCC(O)=O ChemAxon formula C20H32O6 ChemAxon inchi InChI=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/s1 ChemAxon inchikey ROUDCKODIMKLNO-CTBSXBMHSA-N ChemAxon polar_surface_area 111.9 ChemAxon refractivity 98.96 ChemAxon polarizability 42.05 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 Specdb::CMs 2144 Specdb::CMs 2180 Specdb::CMs 25624 Specdb::CMs 31517 Specdb::CMs 31518 Specdb::CMs 38742 Specdb::CMs 175284 Specdb::MsMs 322771 Specdb::MsMs 322772 Specdb::MsMs 322773 Specdb::MsMs 370768 Specdb::MsMs 370769 Specdb::MsMs 370770 Specdb::MsMs 2269186 Specdb::MsMs 2269187 Specdb::MsMs 2269188 Specdb::MsMs 3073233 Specdb::MsMs 3073234 Specdb::MsMs 3073235 HMDB04241 28269 #<Reference:0x000055ce3248fe08> #<Reference:0x000055ce3248fc50> #<Reference:0x000055ce3248fa98> #<Reference:0x000055ce3248f8e0> #<Reference:0x000055ce3248f548> #<Reference:0x000055ce3248f2f0> #<Reference:0x000055ce3248f0c0> 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