1.0 2011-09-21 00:32:40 UTC 2015-07-21 06:57:47 UTC FDB023631 Prostaglandin D1 Prostaglandin D1 is a prostanoid that elicits contractile and relaxant on isolated human pial arteries with small potency. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 6091419, 16986207) 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] (13E,15S)-9alpha,15-dihydroxy-11-oxoprost-13-en-1-oate (13E,15S)-9alpha,15-dihydroxy-11-oxoprost-13-en-1-oic acid 11-dehydro-Prostaglandin F1a 2-Hydroxy-5-(3S-hydroxy-1-octenyl)-3-oxocyclopentaneheptanoate 2-Hydroxy-5-(3S-hydroxy-1-octenyl)-3-oxocyclopentaneheptanoic acid 5-hydroxy-2-(3-hydroxy-1-octenyl)-3-oxo-Cyclopentaneheptanoate 5-hydroxy-2-(3-hydroxy-1-octenyl)-3-oxo-Cyclopentaneheptanoic acid 5-Hydroxy-2-(3-hydroxy-1-octenyl)-3-oxocyclopentaneheptanoate 5-Hydroxy-2-(3-hydroxy-1-octenyl)-3-oxocyclopentaneheptanoic acid 9a,15-Dihydroxy-11-ketoprost-13-enoate 9a,15-Dihydroxy-11-ketoprost-13-enoic acid 9S,15S-dihydroxy-11-oxo-13E-prostaenoate 9S,15S-dihydroxy-11-oxo-13E-prostaenoic acid PGD1 C20H34O5 354.481 354.240624198 7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]heptanoic acid prostaglandin D1 17968-82-0 CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](CCCCCCC(O)=O)[C@@H](O)CC1=O InChI=1S/C20H34O5/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/h12-13,15-18,21-22H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,18-/m0/s1 CIMMACURCPXICP-PNQRDDRVSA-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 Fatty alcohols Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Alcohol Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclic ketone Cyclopentanol Fatty alcohol 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 Prostaglandins Prostaglandins prostaglandins D Solid logp 3.12 ALOGPS logs -3.67 ALOGPS solubility 7.55e-02 g/l ALOGPS logp 3.59 ChemAxon pka_strongest_acidic 4.45 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]heptanoic acid ChemAxon average_mass 354.481 ChemAxon mono_mass 354.240624198 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](CCCCCCC(O)=O)[C@@H](O)CC1=O ChemAxon formula C20H34O5 ChemAxon inchi InChI=1S/C20H34O5/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/h12-13,15-18,21-22H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,18-/m0/s1 ChemAxon inchikey CIMMACURCPXICP-PNQRDDRVSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 98.32 ChemAxon polarizability 42.16 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21583 Specdb::CMs 38865 Specdb::CMs 153808 Specdb::MsMs 313990 Specdb::MsMs 313991 Specdb::MsMs 313992 Specdb::MsMs 359620 Specdb::MsMs 359621 Specdb::MsMs 359622 Specdb::MsMs 2459488 Specdb::MsMs 2459489 Specdb::MsMs 2459490 Specdb::MsMs 2475701 Specdb::MsMs 2475702 Specdb::MsMs 2475703 HMDB05102 27696 #<Reference:0x000055ce31fe9818> #<Reference:0x000055ce31fe9660> #<Reference:0x000055ce31fe94a8> 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