1.02011-09-21 00:19:29 UTC2015-07-21 06:57:21 UTCFDB0227776,15-Diketo,13,14-dihydro-PGF1a6,15-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-PGF1a6,15-diketo,13,14-dihydro-PGF1alpha6,15-dioxo-9S,11R-dihydroxy-13E-prostenoate6,15-dioxo-9S,11R-dihydroxy-13E-prostenoic acid6,15Dk,13,14dh-pgf1aC20H32O6368.4645368.2198887567-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid63446-59-3CCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](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/h10-11,16-19,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t16-,17-,18-,19+/m1/s1VKPWUQVGTPVEMU-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 compoundsOrganic compoundsLipids and lipid-like moleculesFatty AcylsEicosanoidsAliphatic homomonocyclic compoundsAcryloyl compoundsCarboxylic acidsCyclic alcohols and derivativesCyclopentanolsEnonesHydrocarbon derivativesHydroxy fatty acidsKeto fatty acidsKetonesLong-chain fatty acidsMonocarboxylic acids and derivativesOrganic oxidesAcryloyl-groupAlcoholAliphatic homomonocyclic compoundAlpha,beta-unsaturated ketoneCarbonyl groupCarboxylic acidCarboxylic acid derivativeCyclic alcoholCyclopentanolEnoneHydrocarbon derivativeHydroxy fatty acidKeto fatty acidKetoneLong-chain fatty acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundProstaglandin skeletonSecondary alcoholProstaglandinsprostaglandins FalphaSolidlogp2.04logs-3.35solubility1.65e-01 g/llogp2.21pka_strongest_acidic4.14pka_strongest_basic-2.9iupac7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acidaverage_mass368.4645mono_mass368.219888756smilesCCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](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/h10-11,16-19,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t16-,17-,18-,19+/m1/s1inchikeyVKPWUQVGTPVEMU-QVPQFPIISA-Npolar_surface_area111.9refractivity99.1polarizability41.09rotatable_bond_count13acceptor_count6donor_count3physiological_charge-1formal_charge0Specdb::CMs10512Specdb::CMs38209Specdb::CMs174729Specdb::MsMs84639Specdb::MsMs84640Specdb::MsMs84641Specdb::MsMs146535Specdb::MsMs146536Specdb::MsMs146537Specdb::MsMs2693997Specdb::MsMs2693998Specdb::MsMs2693999Specdb::MsMs2985437Specdb::MsMs2985438Specdb::MsMs2985439HMDB01979#<Reference:0x000055567561bf68>#<Reference:0x000055567561bd38>#<Reference:0x000055567561ba90>#<Reference:0x000055567561b838>#<Reference:0x000055567561b5e0>#<Reference:0x000055567561b3b0>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