1.0 2011-09-21 00:15:53 UTC 2015-07-21 06:57:15 UTC FDB022560 Prostaglandin I2 Prostaglandin I2 or prostacyclin (or PGI2) is a member of the family of lipid molecules known as eicosanoids. It is produced in endothelial cells from prostaglandin H2 (PGH2) by the action of the enzyme prostacyclin synthase. It is a powerful vasodilator and inhibits platelet aggregation. Prostaglandin I2 is the main prostaglandin synthesized by the blood vessel wall. This suggests that it may play an important role in limiting platelet-mediated thrombosis. In particular, prostacyclin (PGI2) chiefly prevents formation of the platelet plug involved in primary hemostasis (a part of blood clot formation). The sodium salt (known as epoprostenol) has been used to treat primary pulmonary hypertension. Prostacyclin (PGI2) is released by healthy endothelial cells and performs its function through a paracrine signaling cascade that involves G protein-coupled receptors on nearby platelets and endothelial cells. The platelet Gs protein-coupled receptor (prostacyclin receptor) is activated when it binds to PGI2. This activation, in turn, signals adenylyl cyclase to produce cAMP. cAMP goes on to inhibit any undue platelet activation (in order to promote circulation) and also counteracts any increase in cytosolic calcium levels which would result from thromboxane A2 (TXA2) binding (leading to platelet activation and subsequent coagulation). PGI2 also binds to endothelial prostacyclin receptors and in the same manner raise cAMP levels in the cytosol. This cAMP then goes on to activate protein kinase A (PKA). PKA then continues the cascade by inhibiting myosin light-chain kinase which leads to smooth muscle relaxation and vasodilation. Notably, PGI2 and TXA2 work as antagonists. PGI2 is stable in basic buffers (pH=8), but it is rapidly hydrolyzed to 6-keto PGF1alpha in neutral or acidic solutions. The half-life is short both in vivo and in vitro, ranging from 30 seconds to a few minutes. PGI2 is administered by continuous infusion in humans for the treatment of idiopathic pulmonary hypertension. 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)-6,9a-epoxy-11a,15-dihydroxyprosta-5,13-dienoate (5Z,13E,15S)-6,9a-epoxy-11a,15-dihydroxyprosta-5,13-dienoic acid (5Z,13E)-(15S)-6,9-alpha-epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoate (5Z,13E)-(15S)-6,9-alpha-epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoic acid (5Z,13E)-(15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dienoate (5Z,13E)-(15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dienoic acid (5Z,13e)-(15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoate (5Z,13e)-(15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoic acid (5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoate (5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoic acid (5Z,13e)-(15S)-6,9α-epoxy-11α,15-dihydroxyprosta-5,13-dienoate (5Z,13e)-(15S)-6,9α-epoxy-11α,15-dihydroxyprosta-5,13-dienoic acid (5Z,9a,11a,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oate (5Z,9a,11a,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid (5Z,9alpha,11alpha,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oate (5Z,9alpha,11alpha,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid (5Z,9α,11α,13e,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oate (5Z,9α,11α,13e,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acid Epoprostenol Flolan PGI2 PGX prostacyclin prostacycline Prostaglandin I2 Prostaglandin X Vasocyclin C20H32O5 352.4651 352.224974134 5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid epoprostenol 35121-78-9 [H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(O2)=CCCCC(O)=O InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8?/t14-,16+,17+,18+,19-/m0/s1 KAQKFAOMNZTLHT-VVUHWYTRSA-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 heteropolycyclic compounds Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Fatty alcohols Heterocyclic fatty acids Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Medium-chain hydroxy acids and derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Secondary alcohols Tetrahydrofurans Alcohol Aliphatic heteropolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Fatty alcohol Heterocyclic fatty acid Hydrocarbon derivative Hydroxy fatty acid Medium-chain fatty acid Medium-chain hydroxy acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Prostaglandin skeleton Secondary alcohol Tetrahydrofuran Solid logp 3.83 ALOGPS logs -3.41 ALOGPS solubility 1.36e-01 g/l ALOGPS logp 2.42 ChemAxon pka_strongest_acidic 4.43 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid ChemAxon average_mass 352.4651 ChemAxon mono_mass 352.224974134 ChemAxon smiles [H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(O2)=CCCCC(O)=O ChemAxon formula C20H32O5 ChemAxon inchi InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8?/t14-,16+,17+,18+,19-/m0/s1 ChemAxon inchikey KAQKFAOMNZTLHT-VVUHWYTRSA-N ChemAxon polar_surface_area 86.99 ChemAxon refractivity 99.01 ChemAxon polarizability 41.59 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 Specdb::MsMs 262275 Specdb::MsMs 262276 Specdb::MsMs 262277 Specdb::MsMs 282207 Specdb::MsMs 282208 Specdb::MsMs 282209 HMDB01335 15552 #<Reference:0x000055ce32840bb0> #<Reference:0x000055ce328409d0> #<Reference:0x000055ce32840818> #<Reference:0x000055ce32840610> #<Reference:0x000055ce32840458> #<Reference:0x000055ce328402a0> #<Reference:0x000055ce328400e8> #<Reference:0x000055ce3283fd28> #<Reference:0x000055ce3283faf8> #<Reference:0x000055ce3283f918> #<Reference:0x000055ce3283f738> #<Reference:0x000055ce3283f580> #<Reference:0x000055ce3283f3c8> #<Reference:0x000055ce3283f008> #<Reference:0x000055ce3283ee28> #<Reference:0x000055ce3283ec48> #<Reference:0x000055ce3283ea90> #<Reference:0x000055ce3283e8d8> #<Reference:0x000055ce3283e720> #<Reference:0x000055ce3283e130> 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 Prostacyclin receptor P43119 PTGIR