1.0 2011-09-21 00:24:58 UTC 2015-07-21 06:57:31 UTC FDB023119 15-Keto-prostaglandin E2 15-keto-PGE2 is one of the prostaglandin E2 metabolites. (PMID 7190512). It is a degradation product produced by 15-hydroxy prostaglandin dehydrogenase (PGDH or 15-PGDH) Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and 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). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype. (PMID: 16978535) 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,13E)-11-alpha-hydroxy-9,15-dioxoprost-5,13-dienoate (5Z,13E)-11-alpha-hydroxy-9,15-dioxoprost-5,13-dienoic acid (5Z,13e)-11a-Hydroxy-9,15-dioxoprost-13-enoate (5Z,13e)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid (5Z,13e)-11alpha-Hydroxy-9,15-dioxoprost-13-enoate (5Z,13e)-11alpha-Hydroxy-9,15-dioxoprost-13-enoic acid (5Z,13e)-11α-hydroxy-9,15-dioxoprost-13-enoate (5Z,13e)-11α-hydroxy-9,15-dioxoprost-13-enoic acid (5Z)-(13E)-11-alpha-hydroxy-9,15-dioxoprosta-5,13-dienoate (5Z)-(13E)-11-alpha-hydroxy-9,15-dioxoprosta-5,13-dienoic acid (5Z)-(15S)-11a-Hydroxy-9,15-dioxoprosta-13-enoate (5Z)-(15S)-11a-Hydroxy-9,15-dioxoprosta-13-enoic acid (5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprosta-13-enoate (5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprosta-13-enoic acid (5Z)-(15S)-11α-hydroxy-9,15-dioxoprosta-13-enoate (5Z)-(15S)-11α-hydroxy-9,15-dioxoprosta-13-enoic acid 15-Deoxy-15-oxo-prostaglandin e2 15-Keto-PGE2 15-keto-PGE2-alpha 15-Ketoprostaglandin E2 15-Oxo-PGE2 15-oxo-PGE2-alpha C20H30O5 350.4492 350.20932407 7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-(3-oxooct-1-en-1-yl)cyclopentyl]hept-5-enoic acid 7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-(3-oxooct-1-en-1-yl)cyclopentyl]hept-5-enoic acid 26441-05-4 [H][C@@]1(O)CC(=O)[C@]([H])(CC=CCCCC(O)=O)[C@@]1([H])C=CC(=O)CCCCC InChI=1S/C20H30O5/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/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t16-,17-,19-/m1/s1 YRTJDWROBKPZNV-ZHALLVOQSA-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 Cyclic ketones Cyclopentanols Enones Hydrocarbon derivatives Hydroxy fatty acids 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 Cyclic ketone 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 3.27 ALOGPS logs -3.78 ALOGPS solubility 5.83e-02 g/l ALOGPS logp 3.64 ChemAxon pka_strongest_acidic 4.3 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac 7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-(3-oxooct-1-en-1-yl)cyclopentyl]hept-5-enoic acid ChemAxon average_mass 350.4492 ChemAxon mono_mass 350.20932407 ChemAxon smiles [H][C@@]1(O)CC(=O)[C@]([H])(CC=CCCCC(O)=O)[C@@]1([H])C=CC(=O)CCCCC ChemAxon formula C20H30O5 ChemAxon inchi InChI=1S/C20H30O5/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/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t16-,17-,19-/m1/s1 ChemAxon inchikey YRTJDWROBKPZNV-ZHALLVOQSA-N ChemAxon polar_surface_area 91.67 ChemAxon refractivity 98.54 ChemAxon polarizability 39.68 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB03175 #<Reference:0x000055ce31d649f8> #<Reference:0x000055ce31d64840> #<Reference:0x000055ce31d64688> #<Reference:0x000055ce31d644d0> 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