1.0 2011-09-21 01:48:27 UTC 2015-07-21 06:59:36 UTC FDB028991 PS(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) PS(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the docosahexaenoic acid moiety is derived from fish oils. 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-Palmitoleoyl-2-docosahexaenoyl-sn-glycero-3-oserine 1-palmitoleoyl-2-docosahexaenoyl-sn-glycero-3-phosphoserine Atidylserine(16:1/22:6) Atidylserine(16:1N7/22:6N3) Atidylserine(16:1W7/22:6W3) Atidylserine(38:7) Phosphatidylserine(16:1/22:6) Phosphatidylserine(16:1n7/22:6n3) Phosphatidylserine(16:1w7/22:6w3) PS(16:1/22:6) PS(16:1n7/22:6n3) PS(16:1w7/22:6w3) PS(38:7) PSer(16:1/22:6) PSer(16:1n7/22:6n3) PSer(16:1w7/22:6w3) pSer(38:7) C44H72NO10P 806.0169 805.489384041 (2S)-2-amino-3-({[(2R)-2-(docosa-4,7,10,13,16,19-hexaenoyloxy)-3-(hexadec-9-enoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid (2S)-2-amino-3-{[(2R)-2-(docosa-4,7,10,13,16,19-hexaenoyloxy)-3-(hexadec-9-enoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid [H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC=CCCCCCC)OC(=O)CCC=CCC=CCC=CCC=CCC=CCC=CCC)C(O)=O InChI=1S/C44H72NO10P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-43(47)55-40(38-53-56(50,51)54-39-41(45)44(48)49)37-52-42(46)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h5,7,11,13-14,16-18,20-21,24,26,30,32,40-41H,3-4,6,8-10,12,15,19,22-23,25,27-29,31,33-39,45H2,1-2H3,(H,48,49)(H,50,51)/t40-,41+/m1/s1 JFVIHLIFBOBUBC-ZFESHMOZSA-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. Phosphatidylserines Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphoserines Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acid esters Carboxylic acids Dialkyl phosphates Fatty acid esters Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Organic oxides Organopnictogen compounds Phosphoethanolamines Tricarboxylic acids and derivatives Aliphatic acyclic compound Alkyl phosphate Alpha-amino acid Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Diacyl-glycerol-3-phosphoserine Dialkyl phosphate Fatty acid ester Fatty acyl Hydrocarbon derivative L-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organonitrogen compound Organooxygen compound Organopnictogen compound Phosphoethanolamine Phosphoric acid ester Primary aliphatic amine Primary amine Tricarboxylic acid or derivatives Solid logp 4.85 ALOGPS logs -6.98 ALOGPS solubility 8.46e-05 g/l ALOGPS logp 9.63 ChemAxon pka_strongest_acidic 1.47 ChemAxon pka_strongest_basic 9.38 ChemAxon iupac (2S)-2-amino-3-({[(2R)-2-(docosa-4,7,10,13,16,19-hexaenoyloxy)-3-(hexadec-9-enoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid ChemAxon average_mass 806.0169 ChemAxon mono_mass 805.489384041 ChemAxon smiles [H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC=CCCCCCC)OC(=O)CCC=CCC=CCC=CCC=CCC=CCC=CCC)C(O)=O ChemAxon formula C44H72NO10P ChemAxon inchi InChI=1S/C44H72NO10P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-43(47)55-40(38-53-56(50,51)54-39-41(45)44(48)49)37-52-42(46)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h5,7,11,13-14,16-18,20-21,24,26,30,32,40-41H,3-4,6,8-10,12,15,19,22-23,25,27-29,31,33-39,45H2,1-2H3,(H,48,49)(H,50,51)/t40-,41+/m1/s1 ChemAxon inchikey JFVIHLIFBOBUBC-ZFESHMOZSA-N ChemAxon polar_surface_area 171.68 ChemAxon refractivity 232.26 ChemAxon polarizability 92.04 ChemAxon rotatable_bond_count 39 ChemAxon acceptor_count 7 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB12373 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 2-acylglycerol O-acyltransferase 2 Q3SYC2 MOGAT2 Lactadherin Q08431 MFGE8 Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2 O15357 INPPL1 Phosphatidylserine decarboxylase proenzyme Q9UG56 PISD Phosphatidylserine synthase 1 P48651 PTDSS1 Phosphatidylserine synthase 2 Q9BVG9 PTDSS2 Phospholipase A1 member A Q53H76 PLA1A Protein kinase C delta-binding protein Q969G5 PRKCDBP Scavenger receptor class B member 1 Q8WTV0 SCARB1