1.0 2011-09-21 00:14:11 UTC 2015-07-21 06:57:12 UTC FDB022448 Prostaglandin F2a Prostaglandin F2a (PGF2) is one of the earliest discovered and most common prostaglandins. It is actively biosynthesized in various organs of mammals and exhibits a variety of biological activities, including contraction of pulmonary arteries. It is used in medicine to induce labor and as an abortifacient. PGF2a binds to the Prostaglandin F2 receptor (PTGFR) which is a member of the G-protein coupled receptor family. PGF2-alpha mediates luteolysis. Luteolysis is the structural and functional degradation of the corpus luteum (CL) that occurs at the end of the luteal phase of both the estrous and menstrual cycles in the absence of pregnancy. PGF2 may also be involved in modulating intraocular pressure and smooth muscle contraction in the uterus and gastrointestinal tract sphincters. 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) 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] (+)-Prostaglandin F2a (5Z,13E,15S)-9a,11a,15-trihydroxyprosta-5,13-dien-1-oate (5Z,13E,15S)-9a,11a,15-trihydroxyprosta-5,13-dien-1-oic acid (5Z,13E)-(15S)-9-alpha,11-alpha,15-trihydroxyprosta-5,13-dienoate (5Z,13E)-(15S)-9-alpha,11-alpha,15-trihydroxyprosta-5,13-dienoic acid (5Z,9a,11a,13E,15S)-9,11,15-trihydroxy-Prosta-5,13-dien-1-oate (5Z,9a,11a,13E,15S)-9,11,15-trihydroxy-Prosta-5,13-dien-1-oic acid (9alpha,11alpha,15)-trihydroxyprosta-(5Z,13E)-dien-1-oate (9alpha,11alpha,15)-trihydroxyprosta-(5Z,13E)-dien-1-oic acid 7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoate 7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid 9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-oate 9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-oic acid 9,11,15-trihydroxyprosta-5Z,13E-dien-1-oate 9,11,15-trihydroxyprosta-5Z,13E-dien-1-oic acid 9a,11a-PGF2 9a,11a-PGF2a 9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoate 9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoic acid Amoglandin Cyclosin Dinifertin Dinoprost Enzaprost Enzaprost F F2a Isoprostane Glandin N l-PGF2-alpha l-Prostaglandin F2-alpha Panacelan PGF2a Prostaglandin F2 Prostaglandin F2a Prostamate Prostarmon F Prostin F 2 alpha Protamodin C20H34O5 354.481 354.240624198 (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid 5-trans-PGF2α 551-11-1 CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,18-,19+/m0/s1 PXGPLTODNUVGFL-UAAPODJFSA-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 Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives 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 Cyclopentanol Fatty acid Hydrocarbon derivative Hydroxy fatty acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Prostaglandin skeleton Secondary alcohol Unsaturated fatty acid Prostaglandins Solid logp 3.11 ALOGPS logs -3.48 ALOGPS solubility 1.17e-01 g/l ALOGPS logp 2.61 ChemAxon pka_strongest_acidic 4.36 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid ChemAxon average_mass 354.481 ChemAxon mono_mass 354.240624198 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,18-,19+/m0/s1 ChemAxon inchikey PXGPLTODNUVGFL-UAAPODJFSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 100.47 ChemAxon polarizability 41.7 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 Specdb::CMs 10003 Specdb::CMs 37944 Specdb::CMs 137454 Specdb::CMs 145188 Specdb::MsMs 288106 Specdb::MsMs 288107 Specdb::MsMs 288108 Specdb::MsMs 327115 Specdb::MsMs 327116 Specdb::MsMs 327117 Specdb::MsMs 438315 Specdb::MsMs 3038663 Specdb::MsMs 3038664 Specdb::MsMs 3038665 Specdb::MsMs 3101477 Specdb::MsMs 3101478 Specdb::MsMs 3101479 HMDB01139 15553 #<Reference:0x000055ce31dc8fc0> #<Reference:0x000055ce31dc8e08> #<Reference:0x000055ce31dc8c50> #<Reference:0x000055ce31dc8a98> #<Reference:0x000055ce31dc88e0> #<Reference:0x000055ce31dc8728> #<Reference:0x000055ce31dc8570> #<Reference:0x000055ce31dc83b8> #<Reference:0x000055ce31dc8200> 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 Carbonyl reductase [NADPH] 1 P16152 CBR1 Carbonyl reductase [NADPH] 3 O75828 CBR3