1.0 2011-09-21 00:19:29 UTC 2015-07-21 06:57:21 UTC FDB022777 6,15-Diketo,13,14-dihydro-PGF1a 6,15-diketo,13,14-dihydro-PGF1 alpha is a minor metabolite of prostacyclin (PGI2). Prostacyclin (PGI2) is one of the major vascular protectors against thrombosis and vasoconstriction, caused by thromboxane A(2). PGI2 inhibits platelet aggregation and vasoconstriction. PGI2 synthase (PGIS), a catalyst of PGI2 formation from prostaglandin H2, is widely distributed and predominantly found in vascular endothelial and smooth muscle cells. PGI2 plays an important cardioprotective role increasingly appreciated in recent years in light of adverse effects of COX-2 inhibitors in clinical trials. This cardioprotection is thought to be mediated, in part, by prostacyclin inhibition of platelet aggregation. Multiple lines of evidence suggest that prostacyclin additionally protects from cardiovascular disease by pleiotropic effects on vascular smooth muscle. PGI2 inhibits proliferation of cultured vascular SMCs by inhibiting cell cycle progression from G1 to S phase. Progression through G1 phase is regulated by the sequential activation of the G1 phase cyclin-dependent kinases (cdks). (PMID: 7000774, 6231483, 16303599, 16533160, 17073611, 17164138) [HMDB] 6,15-diketo-13,14-dihydro-PGF1a 6,15-diketo,13,14-dihydro-PGF1alpha 6,15-dioxo-9S,11R-dihydroxy-13E-prostenoate 6,15-dioxo-9S,11R-dihydroxy-13E-prostenoic acid 6,15Dk,13,14dh-pgf1a C20H32O6 368.4645 368.219888756 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid 63446-59-3 CCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](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/h10-11,16-19,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t16-,17-,18-,19+/m1/s1 VKPWUQVGTPVEMU-QVPQFPIISA-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 Acryloyl compounds Carboxylic acids Cyclic alcohols and derivatives Cyclopentanols Enones Hydrocarbon derivatives Hydroxy fatty acids Keto fatty acids Ketones Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Acryloyl-group Alcohol Aliphatic homomonocyclic compound Alpha,beta-unsaturated ketone Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclopentanol Enone 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 Falpha Solid logp 2.04 ALOGPS logs -3.35 ALOGPS solubility 1.65e-01 g/l ALOGPS logp 2.21 ChemAxon pka_strongest_acidic 4.14 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid ChemAxon average_mass 368.4645 ChemAxon mono_mass 368.219888756 ChemAxon smiles CCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](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/h10-11,16-19,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t16-,17-,18-,19+/m1/s1 ChemAxon inchikey VKPWUQVGTPVEMU-QVPQFPIISA-N ChemAxon polar_surface_area 111.9 ChemAxon refractivity 99.1 ChemAxon polarizability 41.09 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 10512 Specdb::CMs 38209 Specdb::CMs 174729 Specdb::MsMs 84639 Specdb::MsMs 84640 Specdb::MsMs 84641 Specdb::MsMs 146535 Specdb::MsMs 146536 Specdb::MsMs 146537 Specdb::MsMs 2693997 Specdb::MsMs 2693998 Specdb::MsMs 2693999 Specdb::MsMs 2985437 Specdb::MsMs 2985438 Specdb::MsMs 2985439 HMDB01979 #<Reference:0x000055ce304a5b38> #<Reference:0x000055ce304a5980> #<Reference:0x000055ce304a56d8> #<Reference:0x000055ce304a5520> #<Reference:0x000055ce304a5340> #<Reference:0x000055ce304a5188> 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