1.0 2011-09-21 00:15:06 UTC 2015-07-21 06:57:14 UTC FDB022509 15-Keto-13,14-dihydroprostaglandin A2 13,14-dihydro-15-keto PGA2 is produced via non-enzymatic dehydration of 13,14-dihydro-15-keto PGE2. PGE2 is the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). (PMID: 16978535, 7384561, 7384560) 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] (5Z)-9,15-dioxo-Prosta-5,10-dien-1-oate (5Z)-9,15-dioxo-Prosta-5,10-dien-1-oic acid 15-Keto-13,14-dihydro-pga2 9,15-dioxo-5Z,10-prostadienoate 9,15-dioxo-5Z,10-prostadienoic acid dhk-PGA2 C20H30O4 334.4498 334.214409448 7-[(1R,5S)-2-oxo-5-(3-oxooctyl)cyclopent-3-en-1-yl]hept-5-enoic acid 7-[(1R,5S)-2-oxo-5-(3-oxooctyl)cyclopent-3-en-1-yl]hept-5-enoic acid 74872-89-2 [H][C@]1(CCC(=O)CCCCC)C=CC(=O)[C@]1([H])CC=CCCCC(O)=O InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,13,15-16,18H,2-3,5-6,8-12,14H2,1H3,(H,23,24)/t16-,18+/m0/s1 FMKLAIBZMCURLI-FUHWJXTLSA-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 ketones Hydrocarbon derivatives Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Unsaturated fatty acids Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic ketone Fatty acid Hydrocarbon derivative Ketone Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Prostaglandin skeleton Unsaturated fatty acid Solid logp 4.13 ALOGPS logs -4.46 ALOGPS solubility 1.16e-02 g/l ALOGPS logp 4.79 ChemAxon pka_strongest_acidic 4.35 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 7-[(1R,5S)-2-oxo-5-(3-oxooctyl)cyclopent-3-en-1-yl]hept-5-enoic acid ChemAxon average_mass 334.4498 ChemAxon mono_mass 334.214409448 ChemAxon smiles [H][C@]1(CCC(=O)CCCCC)C=CC(=O)[C@]1([H])CC=CCCCC(O)=O ChemAxon formula C20H30O4 ChemAxon inchi InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,13,15-16,18H,2-3,5-6,8-12,14H2,1H3,(H,23,24)/t16-,18+/m0/s1 ChemAxon inchikey FMKLAIBZMCURLI-FUHWJXTLSA-N ChemAxon polar_surface_area 71.44 ChemAxon refractivity 97.1 ChemAxon polarizability 39.09 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB01244 #<Reference:0x000055ce3049b408> #<Reference:0x000055ce3049b250> #<Reference:0x000055ce3049b098> 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