1.0 2011-09-21 00:23:41 UTC 2025-11-19 02:43:05 UTC FDB023040 Prostaglandin A1 Prostaglandin A1 (PGA1, a prostaglandin characterized by a cyclopentenone structure) has a fundamental structure common to punaglandin and clavulone, the antitumor eicosanoids discovered in marine organisms such as corals. It is well established that PGA1, which exert potent antiviral activity in several DNA and RNA virus models, induce heat shock protein (hsp)70 syntheses through cycloheximide sensitive activation of heat shock transcription factor. Antitumor prostaglandins are actively incorporated through cell membrane and control gene expression. P53 (protein 53, is a transcription factor that regulates the cell cycle and functions as a tumor suppressor) independent expression of p21 (also known as cyclin-dependent kinase inhibitor 1A or CDKN1A, is a human gene on chromosome 6 (location 6p21.2), that encodes a cyclin-dependent kinase) and gadd 45 (growth arrest and DNA-damage-inducible, alpha 45, a major breast cancer (BRCA1) target is the DNA damage-responsive gene GADD45) activation of peroxisome proliferative activated receptor gamma (PPARgamma) are involved in antitumor mechanism of these prostaglandins. At the low concentration, these prostaglandins exhibit physiological or pathological activity such as osteoblast calcification, promotion of colon cancer cell proliferation. One of the mechanisms of anti-cancer activity of prostaglandins, has been believed to be that these prostaglandins might have p53 like effect in cells lacking p53. (PMID: 7988663, 11104898) 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)-15-hydroxy-9-oxo-Prosta-10,13-dien-1-oate (13E,15S)-15-hydroxy-9-oxo-Prosta-10,13-dien-1-oic acid (13e)-(15S)-15-Hydroxy-9-oxoprosta-10,13-dienoate (13e)-(15S)-15-Hydroxy-9-oxoprosta-10,13-dienoic acid 15-hydroxy-9-oxoprosta-10,13-dienoate 15-hydroxy-9-oxoprosta-10,13-dienoic acid 15a-Hydroxy-9-ketoprosta-10,13-dienoate 15a-Hydroxy-9-ketoprosta-10,13-dienoic acid 15a-Hydroxy-9-oxo-10,13E-prostadienoate 15a-Hydroxy-9-oxo-10,13E-prostadienoic acid 2-(3-hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoate 2-(3-hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoic acid 2-(3-hydroxy-1-octenyl)-5-oxo-3-Cyclopentene-1-heptanoate 2-(3-hydroxy-1-octenyl)-5-oxo-3-Cyclopentene-1-heptanoic acid PGA1 Prostaglandin A1 Prostaglandin E1-217 C20H32O4 336.4657 336.230059512 7-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]heptanoic acid prostaglandin A1 14152-28-4 CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(O)=O InChI=1S/C20H32O4/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/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+/m0/s1 BGKHCLZFGPIKKU-LDDQNKHRSA-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 Fatty alcohols Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Alcohol Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic ketone 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 A Solid logp 4.21 ALOGPS logs -4.35 ALOGPS solubility 1.49e-02 g/l ALOGPS logp 4.74 ChemAxon pka_strongest_acidic 4.45 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 7-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]heptanoic acid ChemAxon average_mass 336.4657 ChemAxon mono_mass 336.230059512 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(O)=O ChemAxon formula C20H32O4 ChemAxon inchi InChI=1S/C20H32O4/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/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+/m0/s1 ChemAxon inchikey BGKHCLZFGPIKKU-LDDQNKHRSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 97.97 ChemAxon polarizability 40.11 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 19226 Specdb::CMs 38455 Specdb::CMs 167888 Specdb::MsMs 308710 Specdb::MsMs 308711 Specdb::MsMs 308712 Specdb::MsMs 352969 Specdb::MsMs 352970 Specdb::MsMs 352971 Specdb::MsMs 2765180 Specdb::MsMs 2765181 Specdb::MsMs 2765182 Specdb::MsMs 2944048 Specdb::MsMs 2944049 Specdb::MsMs 2944050 HMDB02656 15545 #<Reference:0x000055ce32fd4c28> #<Reference:0x000055ce32fd4a48> #<Reference:0x000055ce32fd47c8> #<Reference:0x000055ce32fd4610> #<Reference:0x000055ce32fd4408> #<Reference:0x000055ce32fd41d8> #<Reference:0x000055ce32fd4020> 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