1.02011-09-21 01:49:31 UTC2015-07-21 06:59:37 UTCFDB029061PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines 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. PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)), in particular, consists of one chain of docosahexaenoic acid at the C-1 position and one chain of oleic acid at the C-2 position. The docosahexaenoic acid moiety is derived from fish oils, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids.
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. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. [HMDB]1-Docosahexaenoyl-2-oleoyl-sn-glycero-3-oserine1-docosahexaenoyl-2-oleoyl-sn-glycero-3-phosphoserineAtidylserine(22:6/18:1)Atidylserine(22:6N3/18:1N9)Atidylserine(22:6W3/18:1W9)Phosphatidylserine(22:6/18:1)Phosphatidylserine(22:6n3/18:1n9)Phosphatidylserine(22:6w3/18:1w9)PS(22:6/18:1)PS(22:6n3/18:1n9)PS(22:6w3/18:1w9)PSer(22:6/18:1)PSer(22:6n3/18:1n9)PSer(22:6w3/18:1w9)C46H76NO10P834.0701833.520684169(2S)-2-amino-3-({[(2R)-3-(docosa-4,7,10,13,16,19-hexaenoyloxy)-2-(octadec-9-enoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid(2S)-2-amino-3-{[(2R)-3-(docosa-4,7,10,13,16,19-hexaenoyloxy)-2-(octadec-9-enoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCC=CCC=CCC=CCC=CCC=CCC=CCC)OC(=O)CCCCCCCC=CCCCCCCCC)C(O)=OInChI=1S/C46H76NO10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-25-27-29-31-33-35-37-44(48)54-39-42(40-55-58(52,53)56-41-43(47)46(50)51)57-45(49)38-36-34-32-30-28-26-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17-19,21-23,25,27,31,33,42-43H,3-4,6,8-10,12,14-16,20,24,26,28-30,32,34-41,47H2,1-2H3,(H,50,51)(H,52,53)/t42-,43+/m1/s1RLZWFRUSWOIHNV-QAZBPYKKSA-N belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.PhosphatidylserinesOrganic compoundsLipids and lipid-like moleculesGlycerophospholipidsGlycerophosphoserinesAliphatic acyclic compoundsAmino acidsCarbonyl compoundsCarboxylic acid estersCarboxylic acidsDialkyl phosphatesFatty acid estersHydrocarbon derivativesL-alpha-amino acidsMonoalkylaminesOrganic oxidesOrganopnictogen compoundsPhosphoethanolaminesTricarboxylic acids and derivativesAliphatic acyclic compoundAlkyl phosphateAlpha-amino acidAlpha-amino acid or derivativesAmineAmino acidAmino acid or derivativesCarbonyl groupCarboxylic acidCarboxylic acid derivativeCarboxylic acid esterDiacyl-glycerol-3-phosphoserineDialkyl phosphateFatty acid esterFatty acylHydrocarbon derivativeL-alpha-amino acidOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhosphoethanolaminePhosphoric acid esterPrimary aliphatic aminePrimary amineTricarboxylic acid or derivativesSolidlogp5.13logs-7.09solubility6.74e-05 g/llogp10.52pka_strongest_acidic1.47pka_strongest_basic9.38iupac(2S)-2-amino-3-({[(2R)-3-(docosa-4,7,10,13,16,19-hexaenoyloxy)-2-(octadec-9-enoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acidaverage_mass834.0701mono_mass833.520684169smiles[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCC=CCC=CCC=CCC=CCC=CCC=CCC)OC(=O)CCCCCCCC=CCCCCCCCC)C(O)=OformulaC46H76NO10PinchiInChI=1S/C46H76NO10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-25-27-29-31-33-35-37-44(48)54-39-42(40-55-58(52,53)56-41-43(47)46(50)51)57-45(49)38-36-34-32-30-28-26-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17-19,21-23,25,27,31,33,42-43H,3-4,6,8-10,12,14-16,20,24,26,28-30,32,34-41,47H2,1-2H3,(H,50,51)(H,52,53)/t42-,43+/m1/s1inchikeyRLZWFRUSWOIHNV-QAZBPYKKSA-Npolar_surface_area171.68refractivity241.46polarizability96.58rotatable_bond_count41acceptor_count7donor_count3physiological_charge-1formal_charge0HMDB12445AnatidaeType 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 scrofa98232-acylglycerol O-acyltransferase 2Q3SYC2MOGAT2LactadherinQ08431MFGE8Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2O15357INPPL1Phosphatidylserine decarboxylase proenzymeQ9UG56PISDPhosphatidylserine synthase 1P48651PTDSS1Phosphatidylserine synthase 2Q9BVG9PTDSS2Phospholipase A1 member AQ53H76PLA1AProtein kinase C delta-binding proteinQ969G5PRKCDBPScavenger receptor class B member 1Q8WTV0SCARB1