1.0 2011-09-21 00:24:20 UTC 2015-07-21 06:57:30 UTC FDB023077 6-Keto-prostaglandin F1a 6-keto-Prostaglandin F1a is the physiologically active and stable metabolite of prostacyclin. (A prostaglandin found in nearly all mammalian tissue that is a powerful vasodilator and inhibits platelet aggregation; it is biosynthesized enzymatically from prostaglandin endoperoxides in human vascular tissue; the sodium salt has been also used to treat primary pulmonary hypertension (Hypertension, Pulmonary). A delayed and prolonged increase in 6-keto-PGF1 alpha is reported in animals with septic shock, i.e., those with fecal peritonitis or cecal ligation. 6-keto-Prostaglandin F1a plasma levels has been found increased in patients with epidemic hemorrhagic fever, in patients with acute obstructive suppurative cholangitis, in patients with gynecologic cancer and has significant correlation with the level of high density lipoprotein cholesterol in plasma. (PMID 1976492, 2298410, 2379443, 2111556) 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-PGF1a 6-Keto-PGF1alpha 6-keto-PGF1α 6-Keto-prostaglandin F1a 6-Keto-prostaglandin F1alpha 6-keto-Prostaglandin F1α 6-Ketoprostaglandin F1 alpha 6-Ketoprostaglandin F1a 6-Ketoprostaglandin F1alpha 6-Ketoprostaglandin F1α 6-oxo-9S,11R,15S-trihydroxy-13E-prostenoate 6-oxo-9S,11R,15S-trihydroxy-13E-prostenoic acid 6-Oxo-PGF1a 6-Oxo-PGF1alpha 6-oxo-PGF1α 6-oxo-prostaglandin F1alpha 6-Oxoprostaglandin F1a 6-Oxoprostaglandin F1alpha 6-Oxoprostaglandin F1α C20H34O6 370.4804 370.23553882 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid 6 keto PGF1 α 58962-34-8 CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(O)=O InChI=1S/C20H34O6/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/h10-11,14,16-19,21,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+,19-/m0/s1 KFGOFTHODYBSGM-ZUNNJUQCSA-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 Cyclopentanols Fatty alcohols Hydrocarbon derivatives Hydroxy fatty acids Keto fatty acids Ketones Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Alcohol Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol 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 Falpha Solid logp 1.75 ALOGPS logs -2.91 ALOGPS solubility 4.59e-01 g/l ALOGPS logp 1.79 ChemAxon pka_strongest_acidic 4.14 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid ChemAxon average_mass 370.4804 ChemAxon mono_mass 370.23553882 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(O)=O ChemAxon formula C20H34O6 ChemAxon inchi InChI=1S/C20H34O6/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/h10-11,14,16-19,21,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+,19-/m0/s1 ChemAxon inchikey KFGOFTHODYBSGM-ZUNNJUQCSA-N ChemAxon polar_surface_area 115.06 ChemAxon refractivity 100 ChemAxon polarizability 42.48 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 Specdb::CMs 2145 Specdb::CMs 26578 Specdb::CMs 31428 Specdb::CMs 38489 Specdb::CMs 146545 Specdb::MsMs 105576 Specdb::MsMs 105577 Specdb::MsMs 105578 Specdb::MsMs 172095 Specdb::MsMs 172096 Specdb::MsMs 172097 Specdb::MsMs 2676403 Specdb::MsMs 2676404 Specdb::MsMs 2676405 Specdb::MsMs 3029411 Specdb::MsMs 3029412 Specdb::MsMs 3029413 HMDB02886 28158 #<Reference:0x000055ce307b0eb8> #<Reference:0x000055ce307b0d00> #<Reference:0x000055ce307b0aa8> #<Reference:0x000055ce307b0878> #<Reference:0x000055ce307b0620> #<Reference:0x000055ce307b0378> #<Reference:0x000055ce307b00f8> #<Reference:0x000055ce307afef0> #<Reference:0x000055ce307afd10> #<Reference:0x000055ce307afae0> #<Reference:0x000055ce307af860> #<Reference:0x000055ce307af5e0> 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