1.02011-09-21 00:23:41 UTC2015-07-21 06:57:29 UTCFDB023040Prostaglandin A1Prostaglandin 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 acid15-hydroxy-9-oxoprosta-10,13-dienoate15-hydroxy-9-oxoprosta-10,13-dienoic acid15a-Hydroxy-9-ketoprosta-10,13-dienoate15a-Hydroxy-9-ketoprosta-10,13-dienoic acid15a-Hydroxy-9-oxo-10,13E-prostadienoate15a-Hydroxy-9-oxo-10,13E-prostadienoic acid2-(3-hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoate2-(3-hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoic acid2-(3-hydroxy-1-octenyl)-5-oxo-3-Cyclopentene-1-heptanoate2-(3-hydroxy-1-octenyl)-5-oxo-3-Cyclopentene-1-heptanoic acidPGA1Prostaglandin A1Prostaglandin E1-217C20H32O4336.4657336.2300595127-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]heptanoic acidprostaglandin A114152-28-4CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(O)=OInChI=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/s1BGKHCLZFGPIKKU-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 compoundsOrganic compoundsLipids and lipid-like moleculesFatty AcylsEicosanoidsAliphatic homomonocyclic compoundsCarboxylic acidsCyclic ketonesFatty alcoholsHydrocarbon derivativesHydroxy fatty acidsLong-chain fatty acidsMonocarboxylic acids and derivativesOrganic oxidesSecondary alcoholsAlcoholAliphatic homomonocyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeCyclic ketoneFatty alcoholHydrocarbon derivativeHydroxy fatty acidKetoneLong-chain fatty acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundProstaglandin skeletonSecondary alcoholProstaglandinsprostaglandins ASolidlogp4.21logs-4.35solubility1.49e-02 g/llogp4.74pka_strongest_acidic4.45pka_strongest_basic-1.6iupac7-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]heptanoic acidaverage_mass336.4657mono_mass336.230059512smilesCCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(O)=OformulaC20H32O4inchiInChI=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/s1inchikeyBGKHCLZFGPIKKU-LDDQNKHRSA-Npolar_surface_area74.6refractivity97.97polarizability40.11rotatable_bond_count13acceptor_count4donor_count2physiological_charge-1formal_charge0Specdb::CMs19226Specdb::CMs38455Specdb::CMs167888Specdb::MsMs308710Specdb::MsMs308711Specdb::MsMs308712Specdb::MsMs352969Specdb::MsMs352970Specdb::MsMs352971Specdb::MsMs2765180Specdb::MsMs2765181Specdb::MsMs2765182Specdb::MsMs2944048Specdb::MsMs2944049Specdb::MsMs2944050HMDB0265615545#<Reference:0x0000555675c6b7b0>#<Reference:0x0000555675c6b5d0>#<Reference:0x0000555675c6b3a0>#<Reference:0x0000555675c6b1e8>#<Reference:0x0000555675c6af68>#<Reference:0x0000555675c6ac70>#<Reference:0x0000555675c6aa68>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823