1.02011-09-21 01:18:30 UTC2015-07-21 06:58:58 UTCFDB027006PI(18:0/20:4(8Z,11Z,14Z,17Z))PI(18:0/20:4(8Z,11Z,14Z,17Z)) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols 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 18 and 20 carbons are the most common. PI(18:0/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the eicsoatetraenoic acid moiety is derived from fish oils. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.
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. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. [HMDB]1-Octadecanoyl-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-O-(1'-myo-inositol)1-octadecanoyl-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phospho-(1'-myo-inositol)1-Stearoyl-2-eicsoatetraenoyl-sn-glycero-3-oinositol1-stearoyl-2-eicsoatetraenoyl-sn-glycero-3-phosphoinositolAtidylinositol(18:0/20:4N3)Atidylinositol(18:0/20:4W3)Phosphatidylinositol(18:0/20:4n3)Phosphatidylinositol(18:0/20:4w3)PI(18:0/20:4n3)PI(18:0/20:4w3)PIno(18:0/20:4n3)PIno(18:0/20:4w3)C47H83O13P887.1279886.557129254[(2R)-2-(icosa-8,11,14,17-tetraenoyloxy)-3-(octadecanoyloxy)propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid(2R)-2-(icosa-8,11,14,17-tetraenoyloxy)-3-(octadecanoyloxy)propoxy[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)O[C@@]1([H])C(O)C(O)C(O)[C@@]([H])(O)C1O)OC(=O)CCCCCCC=CCC=CCC=CCC=CCCInChI=1S/C47H83O13P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(49)59-39(38-58-61(55,56)60-47-45(53)43(51)42(50)44(52)46(47)54)37-57-40(48)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,22,24,39,42-47,50-54H,3-4,6,8-10,12,14-16,18,20-21,23,25-38H2,1-2H3,(H,55,56)/t39-,42?,43-,44?,45?,46?,47-/m1/s1OJESNYFIPWSOPO-OXRHWTJRSA-N belongs to the class of organic compounds known as phosphatidylinositols. These are glycerophosphoinositols where the glycerol is esterified with two fatty acids.PhosphatidylinositolsOrganic compoundsLipids and lipid-like moleculesGlycerophospholipidsGlycerophosphoinositolsAliphatic homomonocyclic compoundsCarbonyl compoundsCarboxylic acid estersCyclohexanolsDialkyl phosphatesDicarboxylic acids and derivativesFatty acid estersHydrocarbon derivativesInositol phosphatesOrganic oxidesPolyolsAlcoholAliphatic homomonocyclic compoundAlkyl phosphateCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterCyclic alcoholCyclitol or derivativesCyclohexanolDiacylglycerophosphoinositolDialkyl phosphateDicarboxylic acid or derivativesFatty acid esterFatty acylHydrocarbon derivativeInositol phosphateOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganooxygen compoundPhosphoric acid esterPolyolSecondary alcoholSolidlogp7.40logs-6.32solubility4.20e-04 g/llogp10.21pka_strongest_acidic1.83pka_strongest_basic-3.6iupac[(2R)-2-(icosa-8,11,14,17-tetraenoyloxy)-3-(octadecanoyloxy)propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acidaverage_mass887.1279mono_mass886.557129254smiles[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)O[C@@]1([H])C(O)C(O)C(O)[C@@]([H])(O)C1O)OC(=O)CCCCCCC=CCC=CCC=CCC=CCCformulaC47H83O13PinchiInChI=1S/C47H83O13P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(49)59-39(38-58-61(55,56)60-47-45(53)43(51)42(50)44(52)46(47)54)37-57-40(48)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,22,24,39,42-47,50-54H,3-4,6,8-10,12,14-16,18,20-21,23,25-38H2,1-2H3,(H,55,56)/t39-,42?,43-,44?,45?,46?,47-/m1/s1inchikeyOJESNYFIPWSOPO-OXRHWTJRSA-Npolar_surface_area209.51refractivity242.64polarizability103.62rotatable_bond_count40acceptor_count9donor_count6physiological_charge-1formal_charge0HMDB09816AnatidaeType 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 scrofa9823GPI ethanolamine phosphate transferase 1O95427PIGNGPI ethanolamine phosphate transferase 2Q5H8A4PIGGGPI ethanolamine phosphate transferase 3Q8TEQ8PIGOGPI mannosyltransferase 1Q9H3S5PIGMGPI mannosyltransferase 2Q9NUD9PIGVGPI mannosyltransferase 3Q92521PIGBGPI mannosyltransferase 4Q86VD9PIGZGPI transamidase component PIG-SQ96S52PIGSGPI transamidase component PIG-TQ969N2PIGTN-acetylglucosaminyl-phosphatidylinositol de-N-acetylaseQ9Y2B2PIGLPhosphatidylinositol 3,4,5-trisphosphate 3-phosphatase TPTE2Q6XPS3TPTE2Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 1Q92835INPP5DPhosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2O15357INPPL1Phosphatidylinositol glycan anchor biosynthesis class U proteinQ9H490PIGUPhosphatidylinositol N-acetylglucosaminyltransferase subunit AP37287PIGAPhosphatidylinositol N-acetylglucosaminyltransferase subunit CQ92535PIGCPhosphatidylinositol N-acetylglucosaminyltransferase subunit HQ14442PIGHPhosphatidylinositol N-acetylglucosaminyltransferase subunit QQ9BRB3PIGQPhosphatidylinositol N-acetylglucosaminyltransferase subunit YQ3MUY2PIGYPhosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha isoformP42336PIK3CAPhosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta isoformP42338PIK3CBPhosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta isoformO00329PIK3CDPhosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma isoformP48736PIK3CGPhosphatidylinositol-glycan biosynthesis class F proteinQ07326PIGFPhosphatidylinositol-glycan biosynthesis class W proteinQ7Z7B1PIGWPhosphatidylinositol-glycan biosynthesis class X proteinQ8TBF5PIGXPhosphatidylserine decarboxylase proenzymeQ9UG56PISDPhosphatidylserine synthase 1P48651PTDSS1Phosphatidylserine synthase 2Q9BVG9PTDSS2Phospholipase A1 member AQ53H76PLA1API-PLC X domain-containing protein 1Q9NUJ7PLCXD1PI-PLC X domain-containing protein 2Q0VAA5PLCXD2PI-PLC X domain-containing protein 3Q63HM9PLCXD3