1.0 2011-09-21 00:28:25 UTC 2015-07-21 06:57:39 UTC FDB023345 15-Keto-prostaglandin F2a 15-Keto-prostaglandin F2a is the oxidized product of prostaglandin F2a by 15-hydroxyprostaglandin dehydrogenase, which is present in lung, kidney, placenta and other tissues and catalyzes the NAD- or NADP-dependent dehydrogenation of 15-dydroxyl group. 15-Keto-prostaglandin F2a is further metabolized by its delta13-reduction, beta-oxidation and omega oxidation. The ultimate metabolite is 5a,7a-dihydroxy-11-keto-tetranorprosta-1,16-dioic acid, and excreted in urine. Prostaglandin F2a (PGF2) is one of the earliest discovered and most common prostaglandins is actively biosynthesized in various organs of mammals and exhibits a variety of biological activities, including contraction of pulmonary arteries. PGF2 is mainly synthesized directly from PGH2 by PGH2 9,11-endoperoxide reductase. A small amount of PGF2 is also produced from PGE2 by PGE2 9-ketoreductase. A PGF2 epimer has been reported to exhibit various biological activities, and its levels are increased in bronchoalveolar lavage fluid, plasma, and urine in patients with mastocytosis and bronchial asthma. PGF2 is synthesized from PGD2 by PGD2 11-ketoreductase. (PMID: 16475787, 184496, 5951401, 12432938) 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] 15-Keto-PGF2a 15-Keto-PGF2alpha 15-keto-PGF2α 15-Keto-prostaglandin F2a 15-Keto-prostaglandin F2alpha 15-keto-Prostaglandin F2α 15-Ketoprostaglandin F2a 15-Ketoprostaglandin F2alpha 15-Ketoprostaglandin F2α 15-Oxo PGF-2alpha 15-oxo-prostaglandin F2alpha 9S,11R-Dihydroxy-15-oxo-5Z,13e-prostadienoate 9S,11R-Dihydroxy-15-oxo-5Z,13e-prostadienoic acid C20H32O5 352.4651 352.224974134 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooct-1-en-1-yl)cyclopentyl]hept-5-enoic acid 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooct-1-en-1-yl)cyclopentyl]hept-5-enoic acid 35850-13-6 [H][C@]1(O)C[C@@]([H])(O)[C@]([H])(C=CC(=O)CCCCC)[C@@]1([H])CC=CCCCC(O)=O InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t16-,17-,18+,19-/m1/s1 LOLJEILMPWPILA-AKHDSKFASA-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 Ketones Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Unsaturated fatty acids Acryloyl-group Alcohol Aliphatic homomonocyclic compound Alpha,beta-unsaturated ketone Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclopentanol Enone Fatty acid Hydrocarbon derivative Hydroxy fatty acid Ketone Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Prostaglandin skeleton Secondary alcohol Unsaturated fatty acid Solid logp 3.03 ALOGPS logs -3.58 ALOGPS solubility 9.33e-02 g/l ALOGPS logp 3.02 ChemAxon pka_strongest_acidic 4.36 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooct-1-en-1-yl)cyclopentyl]hept-5-enoic acid ChemAxon average_mass 352.4651 ChemAxon mono_mass 352.224974134 ChemAxon smiles [H][C@]1(O)C[C@@]([H])(O)[C@]([H])(C=CC(=O)CCCCC)[C@@]1([H])CC=CCCCC(O)=O ChemAxon formula C20H32O5 ChemAxon inchi InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t16-,17-,18+,19-/m1/s1 ChemAxon inchikey LOLJEILMPWPILA-AKHDSKFASA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 99.57 ChemAxon polarizability 40.11 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB04240 28442 #<Reference:0x000055ce30a7bb98> #<Reference:0x000055ce30a7b940> #<Reference:0x000055ce30a7b670> #<Reference:0x000055ce30a7b468> #<Reference:0x000055ce30a7b210> #<Reference:0x000055ce30a7b008> 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