1.0 2011-09-21 01:22:48 UTC 2015-07-21 06:59:05 UTC FDB027327 PIP2(22:4(7Z,10Z,13Z,16Z)/16:0) PIP2(22:4(7Z,10Z,13Z,16Z)/16:0) is a phosphatidylinositol bisphosphate. Phosphatidylinositol bisphosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a bisphosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol bisphosphates are generated from phosphatidylinositols which are 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. Phosphatidylinositols bisphosphates 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. PIP2(22:4(7Z,10Z,13Z,16Z)/16:0), in particular, consists of one chain of adrenic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The adrenic acid moiety is derived from animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. The most important phosphatidylinositol bisphosphate in both quantitative and biological terms is 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. Phosphatidylinositols phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol. [HMDB] 1-(7Z,10Z,13Z,16Z-Docosatetraenoyl)-2-hexadecanoyl-sn-glycero-3-O-(1'-myo-inositol-3',4'-bisate) 1-(7Z,10Z,13Z,16Z-docosatetraenoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-myo-inositol-3',4'-bisphosphate) 1-Adrenoyl-2-palmitoyl-sn-glycero-3-oinositol-bisate 1-adrenoyl-2-palmitoyl-sn-glycero-3-phosphoinositol-bisphosphate Atidylinositol diate(22:4N6/16:0) Atidylinositol diate(22:4W6/16:0) Phosphatidylinositol Diphosphate(22:4n6/16:0) Phosphatidylinositol Diphosphate(22:4w6/16:0) PIP2(22:4n6/16:0) PIP2(22:4w6/16:0) PIP2[3',4'](22:4(7Z,10Z,13Z,16Z)/16:0) C47H85O19P3 1047.0877 1046.489790074 {[(4S,6S)-4-({[(2R)-3-(docosa-7,10,13,16-tetraenoyloxy)-2-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2,3,5-trihydroxy-6-(phosphonooxy)cyclohexyl]oxy}phosphonic acid [(4S,6S)-4-{[(2R)-3-(docosa-7,10,13,16-tetraenoyloxy)-2-(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2,3,5-trihydroxy-6-(phosphonooxy)cyclohexyl]oxyphosphonic acid [H][C@@](COC(=O)CCCCCC=CCC=CCC=CCC=CCCCCC)(COP(O)(=O)O[C@@]1([H])C(O)C(O)C(OP(O)(O)=O)[C@@]([H])(OP(O)(O)=O)C1O)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C47H85O19P3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-40(48)61-37-39(63-41(49)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2)38-62-69(59,60)66-45-42(50)43(51)46(64-67(53,54)55)47(44(45)52)65-68(56,57)58/h11,13,17-18,20-21,24-25,39,42-47,50-52H,3-10,12,14-16,19,22-23,26-38H2,1-2H3,(H,59,60)(H2,53,54,55)(H2,56,57,58)/t39-,42?,43?,44?,45+,46?,47+/m1/s1 GHYCRALJEHNAAM-WPFJDRAISA-N belongs to the class of organic compounds known as phosphatidylinositol-4,5-bisphosphates. These are phosphatidylinositol bisphosphates in which the two phosphate groups are at C-4 and C-5 of the inositol moiety. Phosphatidylinositol-4,5-bisphosphates Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphoinositol phosphates Aliphatic homomonocyclic compounds Carbonyl compounds Carboxylic acid esters Cyclohexanols Dialkyl phosphates Dicarboxylic acids and derivatives Fatty acid esters Hydrocarbon derivatives Inositol phosphates Monoalkyl phosphates Organic oxides Phosphatidylinositols Polyols Alcohol Aliphatic homomonocyclic compound Alkyl phosphate Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic alcohol Cyclitol or derivatives Cyclohexanol Diacylglycerophosphoinositol Diacylglycerophosphoinositol-4,5-bisphosphate Dialkyl phosphate Dicarboxylic acid or derivatives Fatty acid ester Fatty acyl Glycerophosphoinositol Hydrocarbon derivative Inositol phosphate Monoalkyl phosphate Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Polyol Secondary alcohol Solid logp 5.97 ALOGPS logs -4.62 ALOGPS solubility 2.52e-02 g/l ALOGPS logp 9.97 ChemAxon pka_strongest_acidic 0.63 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac {[(4S,6S)-4-({[(2R)-3-(docosa-7,10,13,16-tetraenoyloxy)-2-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2,3,5-trihydroxy-6-(phosphonooxy)cyclohexyl]oxy}phosphonic acid ChemAxon average_mass 1047.0877 ChemAxon mono_mass 1046.489790074 ChemAxon smiles [H][C@@](COC(=O)CCCCCC=CCC=CCC=CCC=CCCCCC)(COP(O)(=O)O[C@@]1([H])C(O)C(O)C(OP(O)(O)=O)[C@@]([H])(OP(O)(O)=O)C1O)OC(=O)CCCCCCCCCCCCCCC ChemAxon formula C47H85O19P3 ChemAxon inchi InChI=1S/C47H85O19P3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-40(48)61-37-39(63-41(49)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2)38-62-69(59,60)66-45-42(50)43(51)46(64-67(53,54)55)47(44(45)52)65-68(56,57)58/h11,13,17-18,20-21,24-25,39,42-47,50-52H,3-10,12,14-16,19,22-23,26-38H2,1-2H3,(H,59,60)(H2,53,54,55)(H2,56,57,58)/t39-,42?,43?,44?,45+,46?,47+/m1/s1 ChemAxon inchikey GHYCRALJEHNAAM-WPFJDRAISA-N ChemAxon polar_surface_area 302.57 ChemAxon refractivity 264.39 ChemAxon polarizability 112.48 ChemAxon rotatable_bond_count 44 ChemAxon acceptor_count 13 ChemAxon donor_count 8 ChemAxon physiological_charge -5 ChemAxon formal_charge 0 ChemAxon HMDB10144 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 GPI ethanolamine phosphate transferase 1 O95427 PIGN GPI ethanolamine phosphate transferase 2 Q5H8A4 PIGG GPI ethanolamine phosphate transferase 3 Q8TEQ8 PIGO GPI mannosyltransferase 1 Q9H3S5 PIGM GPI mannosyltransferase 2 Q9NUD9 PIGV GPI mannosyltransferase 3 Q92521 PIGB GPI mannosyltransferase 4 Q86VD9 PIGZ GPI transamidase component PIG-S Q96S52 PIGS GPI transamidase component PIG-T Q969N2 PIGT N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase Q9Y2B2 PIGL Phosphatidylinositol 3,4,5-trisphosphate 3-phosphatase TPTE2 Q6XPS3 TPTE2 Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 1 Q92835 INPP5D Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2 O15357 INPPL1 Phosphatidylinositol glycan anchor biosynthesis class U protein Q9H490 PIGU Phosphatidylinositol N-acetylglucosaminyltransferase subunit A P37287 PIGA Phosphatidylinositol N-acetylglucosaminyltransferase subunit C Q92535 PIGC Phosphatidylinositol N-acetylglucosaminyltransferase subunit H Q14442 PIGH Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q Q9BRB3 PIGQ Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y Q3MUY2 PIGY Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha isoform P42336 PIK3CA Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta isoform P42338 PIK3CB Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta isoform O00329 PIK3CD Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PIK3CG Phosphatidylinositol-glycan biosynthesis class F protein Q07326 PIGF Phosphatidylinositol-glycan biosynthesis class W protein Q7Z7B1 PIGW Phosphatidylinositol-glycan biosynthesis class X protein Q8TBF5 PIGX Phosphatidylserine decarboxylase proenzyme Q9UG56 PISD Phosphatidylserine synthase 1 P48651 PTDSS1 Phosphatidylserine synthase 2 Q9BVG9 PTDSS2 Phospholipase A1 member A Q53H76 PLA1A PI-PLC X domain-containing protein 1 Q9NUJ7 PLCXD1 PI-PLC X domain-containing protein 2 Q0VAA5 PLCXD2 PI-PLC X domain-containing protein 3 Q63HM9 PLCXD3