1.0 2011-09-21 00:16:44 UTC 2015-10-09 22:33:18 UTC FDB022602 Prostaglandin D2 Prostaglandin D2 (or PGD2) is a prostaglandin that is actively produced in various organs such as the brain, spleen, thymus, bone marrow, uterus, ovary, oviduct, testis, prostate and epididymis, and is involved in many physiological events. PGD2 binds to the prostaglandin D2 receptor (PTGDR) which is a G-protein-coupled receptor. Its activity is mainly mediated by G-S proteins that stimulate adenylate cyclase resulting in an elevation of intracellular cAMP and Ca2+. PGD2 promotes sleep; regulates body temperature, olfactory function, hormone release, and nociception in the central nervous system; prevents platelet aggregation; and induces vasodilation and bronchoconstriction. PGD2 is also released from mast cells as an allergic and inflammatory mediator. Prostaglandin H2 is an unstable intermediate formed from PGG2 by the action of cyclooxygenase (COX) in the arachidonate cascade. In mammalian systems, it is efficiently converted into more stable arachidonate metabolites, such as PGD2, PGE2, PGF2a by the action of three groups of enzymes, PGD synthases (PGDS), PGE synthases and PGF synthases, respectively. PGDS catalyzes the isomerization of PGH2 to PGD2. Two types of PGD2 synthase are known. Lipocalin-type PGD synthase is present in cerebrospinal fluid, seminal plasma and may play an important role in male reproduction. Another PGD synthase, hematopoietic PGD synthase is present in the spleen, fallopian tube, endometrial gland cells, extravillous trophoblasts and villous trophoblasts, and perhaps plays an important role in female reproduction. Recent studies demonstrate that PGD2 is probably involved in multiple aspects of inflammation through its dual receptor systems, DP and CRTH2. (PMID: 12148545) 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,15S)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate (5Z,13E,15S)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid (5Z,13E,15S)-9a,15-dihydroxy-11-oxoprosta-5,13-dien-1-oate (5Z,13E,15S)-9a,15-dihydroxy-11-oxoprosta-5,13-dien-1-oic acid (5Z,13e,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoate (5Z,13e,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid (5Z,13e,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate (5Z,13e,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid (5Z,13e,15S)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoate (5Z,13e,15S)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoic acid (5z,13e)-(15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate (5z,13e)-(15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid (5Z,13E)-(15S)-9,15-dihydroxy-11-oxoprosta-5,13-dienoate (5Z,13E)-(15S)-9,15-dihydroxy-11-oxoprosta-5,13-dienoic acid (5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoate (5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid (5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate (5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid (5Z,13e)-(15S)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoate (5Z,13e)-(15S)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoic acid (5Z,9-alpha,13E,15S)-9,15-dihydroxy-11-oxo-Prosta-5,13-dien-1-oate (5Z,9-alpha,13E,15S)-9,15-dihydroxy-11-oxo-Prosta-5,13-dien-1-oic acid (5Z,9alpha,13E,15S)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oate (5Z,9alpha,13E,15S)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oic acid 11-Dehydroprostaglandin F2-a 11-Dehydroprostaglandin F2-alpha 11-Dehydroprostaglandin F2-α 11-Dehydroprostaglandin F2alpha 9S,15S-dihydroxy-11-oxo-5Z,13E-prostadienoate 9S,15S-dihydroxy-11-oxo-5Z,13E-prostadienoic acid PGD2 prostaglandin d2 C20H32O5 352.4651 352.224974134 7-[(1R,2R,5S)-5-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid 7-[(1R,2R,5S)-5-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid 41598-07-6 [H]C(=C[C@@]1([H])C(=O)C[C@]([H])(O)[C@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CCCCC 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/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t15-,16+,17+,18-/m0/s1 BHMBVRSPMRCCGG-MLHJIOFPSA-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 alcohols and derivatives Cyclic ketones Cyclopentanols Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Unsaturated fatty acids Alcohol Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclic ketone Cyclopentanol 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 3.12 ALOGPS logs -3.61 ALOGPS solubility 8.60e-02 g/l ALOGPS logp 3.23 ChemAxon pka_strongest_acidic 4.4 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 7-[(1R,2R,5S)-5-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid ChemAxon average_mass 352.4651 ChemAxon mono_mass 352.224974134 ChemAxon smiles [H]C(=C[C@@]1([H])C(=O)C[C@]([H])(O)[C@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CCCCC 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/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t15-,16+,17+,18-/m0/s1 ChemAxon inchikey BHMBVRSPMRCCGG-MLHJIOFPSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 99.44 ChemAxon polarizability 40.52 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 HMDB01403 15555 PG2 #<Reference:0x000055ce324f09b0> #<Reference:0x000055ce324f07f8> #<Reference:0x000055ce324f0640> #<Reference:0x000055ce324f0488> #<Reference:0x000055ce324f02d0> #<Reference:0x000055ce324f0118> #<Reference:0x000055ce324eff38> #<Reference:0x000055ce324efd80> #<Reference:0x000055ce324efbc8> #<Reference:0x000055ce324efa10> #<Reference:0x000055ce324ef858> #<Reference:0x000055ce324ef6a0> #<Reference:0x000055ce324ef4e8> #<Reference:0x000055ce324ef330> #<Reference:0x000055ce324ef178> #<Reference:0x000055ce324eefc0> #<Reference:0x000055ce324eee08> #<Reference:0x000055ce324eec50> #<Reference:0x000055ce324eea98> #<Reference:0x000055ce324ee8e0> #<Reference:0x000055ce324ee728> 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 Hematopoietic prostaglandin D synthase O60760 HPGDS Prostaglandin-H2 D-isomerase P41222 PTGDS