1.0 2016-09-30 22:32:52 UTC 2020-06-04 20:04:17 UTC BMDB0000564 BMDB00564 PC(16:0/16:0) PC(16:0/16:0), also known as DPPC or 16:0-16:0-PC, belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. Thus, PC(16:0/16:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/16:0) exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. PC(16:0/16:0) exists in all eukaryotes, ranging from yeast to humans. In cattle, PC(16:0/16:0) is involved in the metabolic pathway called phospholipid biosynthesis pathway. 1,2-Bis(hexadecanoyl)-sn-glycero-3-phosphocholine 1,2-Dipalmitoyl-L-lecithin 1,2-Dipalmitoyl-sn-glycero-3-phosphatidylcholine 1,2-Dipalmitoyl-sn-glycero-3-phosphocholine 1,2-Dipalmitoylphosphatidylcholine 1-16:0-2-16:0-Phosphatidylcholine 16:0-16:0-PC Colfosceril palmitate Colfoscerili palmitas Dipalmitoyl phosphatidylcholine Dipalmitoyl-GPC Dipalmitoylphosphatidylcholine GPC(16:0/16:0) GPCho 16:0/16:0 GPCho(16:0/16:0) Palmitate de colfosceril Palmitato de colfoscerilo PC 16:0/16:0 PC(32:0) Phosphatidylcholine 16:0/16:0 Phosphatidylcholine(16:0/16:0) Phosphatidylcholine(32:0) Colfosceril palmitic acid Palmitic acid de colfosceril 1,2-dipalmitoyl-rac-glycero-3-phosphocholine Lecithin PC(16:0/16:0) 1,2-dihexadecanoyl-rac-glycero-3-phosphocholine GPCho(32:0) (R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide hydroxide inner salt (R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide inner salt 1,2-Bis(palmitoyl)-sn-glycero-3-phosphocholine 1,2-Dihexadecanoyl-sn-glycerol-3-phosphorylcholine 1,2-Dipalmitoyl-3-sn-phosphatidylcholine 1,2-Dipalmitoyl-L-3-phosphatidylcholine 1,2-Dipalmitoyl-L-a-lecithin 1,2-Dipalmitoyl-L-a-phosphatidylcholine 1,2-Dipalmitoyl-L-alpha-lecithin 1,2-Dipalmitoyl-L-alpha-phosphatidylcholine 1,2-Dipalmitoyl-L-phosphatidylcholine 1,2-Dipalmitoyl-sn-3-glycerophosphocholine 1,2-Dipalmitoyl-sn-glycero-3-phosphorylcholine 1,2-Dipalmitoyl-sn-glycerol-3-phosphocholine 1,2-Dipalmitoyl-sn-glycerophosphocholine 1,2-Dipalmitoyl-sn-glycerophosphorylcholine 1,2-Dipalmitoyl-sn-glyceryl-3-phosphocholine 1,2-Dipalmitoyl-sn-phosphatidylcholine 1,2-dipalmitoylglycero-3-Phosphocholine 1,2-L-a-Dipalmitoylphosphatidylcholine 1,2-L-alpha-Dipalmitoylphosphatidylcholine b,g-Dipalmitoyl L-a-phosphatidylcholine b,g-Dipalmitoyl L-alpha-phosphatidylcholine b,g-Dipalmitoyl-L-(a)-lecithin b,g-Dipalmitoyl-L-phosphatidylcholine Dihexadecanoyl-sn-glycero-3-phosphocholine Dipalmitoyl L-a-phosphatidylcholine Dipalmitoyl L-alpha-phosphatidylcholine Dipalmitoyl-L-3-glycerylphosphorylcholine Dipalmitoyl-L-a-lecithin Dipalmitoyl-L-a-phosphatidylcholine Dipalmitoyl-L-alpha-lecithin Dipalmitoyl-L-alpha-phosphatidylcholine Dipalmitoyl-sn-3-phosphatidylcholine DPPC L-1,2-Dipalmitoyl-a-lecithin L-1,2-Dipalmitoyl-alpha-lecithin L-1,2-Dipalmitoylphosphatidylcholine L-a-1,2-Dipalmitoyl lecithin L-a-Dipalmitoylecithin L-a-Dipalmitoyllecithin L-a-Dipalmitoylphosphatidylcholine L-a-DPPC L-alpha-1,2-Dipalmitoyl lecithin L-alpha-Dipalmitoylecithin L-alpha-Dipalmitoyllecithin L-alpha-Dipalmitoylphosphatidylcholine L-alpha-DPPC L-b,g-Dipalmitoyl-a-lecithin L-b,g-Dipalmitoyl-a-phosphatidylcholine L-b,g-Dipalmitoyl-alpha-lecithin L-b,g-Dipalmitoyl-alpha-phosphatidylcholine L-b,g-Dipalmitoylphosphatidylcholine L-Dipalmitoyl lecithin L-DPPC PC Aa C32:0 sn-3-Dipalmitoyllecithin 1,2-Dipalmitoyl-GPC 1,2-Distearoyl-glycero-3-phosphocholine C40H80NO8P 734.0389 733.562155053 (2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium 63-89-8 [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1 KILNVBDSWZSGLL-KXQOOQHDSA-N belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphocholines Phosphatidylcholines Amines Carbonyl compounds Carboxylic acid esters Dialkyl phosphates Dicarboxylic acids and derivatives Fatty acid esters Hydrocarbon derivatives Organic oxides Organic salts Organopnictogen compounds Phosphocholines Tetraalkylammonium salts Aliphatic acyclic compound Alkyl phosphate Amine Carbonyl group Carboxylic acid derivative Carboxylic acid ester Diacylglycero-3-phosphocholine Dialkyl phosphate Dicarboxylic acid or derivatives Fatty acid ester Fatty acyl Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic salt Organonitrogen compound Organooxygen compound Organopnictogen compound Phosphocholine Phosphoric acid ester Quaternary ammonium salt Tetraalkylammonium salt Aliphatic acyclic compounds Diacylglycerophosphocholines phosphatidylcholine 32:0 Solid logp 5.29 ALOGPS logs -7.52 ALOGPS logp 8.11 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 734.0389 ChemAxon mono_mass 733.562155053 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC ChemAxon formula C40H80NO8P ChemAxon inchi InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1 ChemAxon inchikey KILNVBDSWZSGLL-KXQOOQHDSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 215.87 ChemAxon polarizability 92 ChemAxon rotatable_bond_count 40 ChemAxon acceptor_count 4 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Phosphatidylcholine Biosynthesis PC(16:0/16:0) SMP0080514 Phosphatidylethanolamine Biosynthesis PE(16:0/16:0) SMP0082317 Phospholipid Biosynthesis SMP0087228 Specdb::NmrTwoD 1366 Specdb::MsMs 666493 Specdb::MsMs 666494 Specdb::MsMs 666495 Specdb::MsMs 1471293 Specdb::MsMs 1473285 Specdb::MsMs 1473286 Specdb::MsMs 1473365 Specdb::MsMs 1473375 Specdb::MsMs 1473376 Specdb::MsMs 1473377 Specdb::MsMs 1475935 Specdb::MsMs 1475936 Specdb::MsMs 1475937 Specdb::MsMs 1475938 Specdb::MsMs 1475939 Specdb::MsMs 1475940 Specdb::MsMs 1475941 Specdb::MsMs 1475942 Specdb::MsMs 1475943 Specdb::MsMs 1475944 Specdb::MsMs 1475945 Specdb::MsMs 1475946 Specdb::MsMs 1475947 Specdb::MsMs 1475948 Specdb::MsMs 1475949 Specdb::NmrOneD 1421 Specdb::NmrOneD 273678 Specdb::NmrOneD 273679 Specdb::NmrOneD 273680 Specdb::NmrOneD 273681 Specdb::NmrOneD 273682 Specdb::NmrOneD 273683 Specdb::NmrOneD 273684 Specdb::NmrOneD 273685 Specdb::NmrOneD 273686 Specdb::NmrOneD 273687 Specdb::NmrOneD 273688 Specdb::NmrOneD 273689 Specdb::NmrOneD 273690 Specdb::NmrOneD 273691 Specdb::NmrOneD 273692 Specdb::NmrOneD 273693 Specdb::NmrOneD 273694 Specdb::NmrOneD 273695 Specdb::NmrOneD 273696 Specdb::NmrOneD 273697 Milk 10.4 +/- 0.4 uM Commercial 1% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 12.5 +/- 0.5 uM Commercial 2% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 15.1 +/- 0.3 uM Commercial 3.25% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 10.2 +/- 0.3 uM Commercial skim milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Ruminal Fluid 0.040 +/- 0.03 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS. Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. 452110 C00157 72999 398235 FDB022121 DB09114 1-2-DIPALMITOYLPHOSPHATIDYLCHOLINE 5548 Bouirig, H.; Eloy, D.; Jardon, P. Formation and reactivity of the singlet oxygen photosensitized by hypericin in the liposomes of dipalmitoylphosphatidylcholine. Evidence of delayed oxidation. Journal de Chimie Physique et de Physico-Chimie Biologique (1992), 89(6), 1391-411. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP00390 Cholinephosphotransferase 1 Q1LZE6 CHPT1 Enzyme BMDBP00420 Phosphatidylethanolamine N-methyltransferase Q7YRH6 PEMT Enzyme BMDBP03194 Phospholipase A2, membrane associated Q56JZ2 PLA2G2A Enzyme