1.02011-09-21 01:29:09 UTC2015-07-21 06:59:13 UTCFDB027740PG(16:1(9Z)/18:2(9Z,12Z))PG(16:1(9Z)/18:2(9Z,12Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(16:1(9Z)/18:2(9Z,12Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the linoleic acid moiety is derived from seed oils. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases.
While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. [HMDB]1-(9Z-Hexadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-O-(1'-glycerol)1-(9Z-hexadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1'-glycerol)1-Palmitoleoyl-2-linoleoyl-sn-glycero-3-oglycerol1-palmitoleoyl-2-linoleoyl-sn-glycero-3-phosphoglycerolAtidylglycerol(16:1/18:2)Atidylglycerol(16:1N7/18:2N6)Atidylglycerol(16:1W7/18:2W6)GPG(16:1/18:2)GPG(16:1n7/18:2n6)GPG(16:1w7/18:2w6)PG(16:1/18:2)PG(16:1n7/18:2n6)PG(16:1w7/18:2w6)Phosphatidylglycerol(16:1/18:2)Phosphatidylglycerol(16:1n7/18:2n6)Phosphatidylglycerol(16:1w7/18:2w6)C40H73O10P744.9754744.494135068[(2S)-2,3-dihydroxypropoxy][(2R)-3-(hexadec-9-enoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy(2R)-3-(hexadec-9-enoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxyphosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC=CCCCCCC)OC(=O)CCCCCCCC=CCC=CCCCCCInChI=1S/C40H73O10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13-14,16-18,37-38,41-42H,3-10,12,15,19-36H2,1-2H3,(H,45,46)/t37-,38+/m0/s1PTJBFPPEYDFAAQ-QPPIDDCLSA-N belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.PhosphatidylglycerolsOrganic compoundsLipids and lipid-like moleculesGlycerophospholipidsGlycerophosphoglycerolsAliphatic acyclic compounds1,2-diolsCarbonyl compoundsCarboxylic acid estersDialkyl phosphatesDicarboxylic acids and derivativesFatty acid estersHydrocarbon derivativesOrganic oxidesPrimary alcoholsSecondary alcohols1,2-diacylglycerophosphoglycerol1,2-diolAlcoholAliphatic acyclic compoundAlkyl phosphateCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterDialkyl phosphateDicarboxylic acid or derivativesFatty acid esterFatty acylHydrocarbon derivativeOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganooxygen compoundPhosphoric acid esterPrimary alcoholSecondary alcoholSolidlogp7.67logs-6.82solubility1.14e-04 g/llogp10.74pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2S)-2,3-dihydroxypropoxy][(2R)-3-(hexadec-9-enoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphinic acidaverage_mass744.9754mono_mass744.494135068smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC=CCCCCCC)OC(=O)CCCCCCCC=CCC=CCCCCCformulaC40H73O10PinchiInChI=1S/C40H73O10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13-14,16-18,37-38,41-42H,3-10,12,15,19-36H2,1-2H3,(H,45,46)/t37-,38+/m0/s1inchikeyPTJBFPPEYDFAAQ-QPPIDDCLSA-Npolar_surface_area148.82refractivity207.86polarizability89.74rotatable_bond_count39acceptor_count6donor_count3physiological_charge-1formal_charge0HMDB10590AnatidaeType 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 scrofa9823Acyl-CoA:lysophosphatidylglycerol acyltransferase 1Q92604LPGAT1