1.0 2011-09-21 00:24:01 UTC 2015-07-21 06:57:29 UTC FDB023060 Prostaglandin A2 Produced by the seminal vessicals: Prostaglandins are a group of lipid compounds that are derived enzymatically from fattyacids. Technically a hormone, the prostanoid class of fatty acid derivatives is a subclass of eicosanoids. Prostaglandin A is cyclopentenone and endogenous metabolite derived from arachidonic acid. Exhibits potent cellular anti-proliferative activity in vivo and in vitro. Excess PGA2 causes an accumulation in both S and G2/M, and a marked decrease in G1. As well there is an increase in DNA content preceeding the G0/G1 peak (indicative of apoptic body formation) mediated by changes in expression levels of Bax and Bcl-2. 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 A2 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoate 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoic acid 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoate 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoic acid 15(S)-Prostaglandin A2 15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylate 15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylic acid 15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoate 15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoic acid Prostaglandin A2 C20H30O4 334.4498 334.214409448 7-{2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl}hept-5-enoic acid 7-{2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl}hept-5-enoic acid 13345-50-1 [H][C@](O)(CCCCC)C=CC1C=CC(=O)C1CC=CCCCC(O)=O InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/t16?,17-,18?/m0/s1 MYHXHCUNDDAEOZ-ADKAHSJRSA-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 ketones Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic ketone 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 4.08 ALOGPS logs -4.21 ALOGPS solubility 2.06e-02 g/l ALOGPS logp 4.38 ChemAxon pka_strongest_acidic 4.4 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 7-{2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl}hept-5-enoic acid ChemAxon average_mass 334.4498 ChemAxon mono_mass 334.214409448 ChemAxon smiles [H][C@](O)(CCCCC)C=CC1C=CC(=O)C1CC=CCCCC(O)=O ChemAxon formula C20H30O4 ChemAxon inchi InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/t16?,17-,18?/m0/s1 ChemAxon inchikey MYHXHCUNDDAEOZ-ADKAHSJRSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 99.09 ChemAxon polarizability 39.13 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 HMDB02752 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