1.0 2016-09-30 23:48:07 UTC 2020-06-04 19:51:03 UTC BMDB0007969 BMDB07969 PC(16:0/16:1(9Z)) PC(16:0/16:1(9Z)), also known as PC(16:0/16:1) or PC(32:1), 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(16:0/16:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/16:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/16:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:0/16:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:0/16:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/16:1(9Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:0/16:1(9Z)) can be biosynthesized from CDP-choline and DG(16:0/16:1(9Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:0/16:1(9Z)) and L-serine can be converted into choline and PS(16:0/16:1(9Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(16:0/16:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/16:1(9Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:0/16:1(9Z)) pathway. (2R)-2-[(9Z)-Hexadec-9-enoyloxy]-3-(palmitoyloxy)propyl 2-(trimethylammonio)ethyl phosphate (2R)-3-(Hexadecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphate (R-(Z))-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-((1-oxo-9-hexadecenyl)oxy)-3,5,9-trioxa-4-phosphapentacosan-1-aminium, hydroxide, inner salt, 4-oxide 1-C16:0-2-C16:1(Omega-7)-phosphatidylcholine 1-Hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphocholine 1-Hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine 1-Hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine zwitterion 1-Palmitoyl-2-palmitoleoyl-GPC 1-Palmitoyl-2-palmitoleoyl-GPC (16:0/16:1) GPC(16:0/16:1) PC(16:0/16:1) PC(16:0/16:1omega7) PC(32:1) Phosphatidylcholine(16:0/16:1) Phosphatidylcholine(16:0/16:1omega7) Phosphatidylcholine(32:1) sn-1-Palmitoyl-2-palmitoleoylphosphatidylcholine (2R)-2-[(9Z)-Hexadec-9-enoyloxy]-3-(palmitoyloxy)propyl 2-(trimethylammonio)ethyl phosphoric acid (2R)-3-(Hexadecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphoric acid Palmitoylpalmitoleoylphosphatidylcholine 1-(16,16,16-Trideuteriopalmitoyl)-2-palmitoleoyl-sn-glycero-3-phosphocholine 1-Palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine, (Z)-isomer (CD3-16.0)(16.1)PC 1-Palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine PPA-GPC GPCho(16:0/16:1) Lecithin GPCho(32:1) 1-Palmitoyl-2-palmitoleoyl-sn-glycero-phosphatidylcholine 1-Palmitoyl-2-palmitoleoylphosphatidylcholine GPC(16:0/16:1(9Z)) GPC(16:0/16:1n7) GPC(16:0/16:1W7) GPC(32:1) GPCho(16:0/16:1(9Z)) GPCho(16:0/16:1n7) GPCho(16:0/16:1W7) L-alpha-1-Palmitoyl-2-palmitoleoylphosphatidylcholine L-Α-1-palmitoyl-2-palmitoleoylphosphatidylcholine PC(16:0/16:1n7) PC(16:0/16:1W7) Phosphatidylcholine(16:0/16:1(9Z)) Phosphatidylcholine(16:0/16:1n7) Phosphatidylcholine(16:0/16:1W7) PC(16:0/16:1(9Z)) C40H78NO8P 732.023 731.546504989 (2-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium lecithin 53595-24-7 CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCC InChI=1S/C40H78NO8P/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/h17,19,38H,6-16,18,20-37H2,1-5H3/b19-17-/t38-/m1/s1 QIBZFHLFHCIUOT-NPBIGWJUSA-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 32:1 Solid logp 5.25 ALOGPS logs -7.47 ALOGPS logp 7.75 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 732.023 ChemAxon mono_mass 731.546504989 ChemAxon smiles CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCC ChemAxon formula C40H78NO8P ChemAxon inchi InChI=1S/C40H78NO8P/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/h17,19,38H,6-16,18,20-37H2,1-5H3/b19-17-/t38-/m1/s1 ChemAxon inchikey QIBZFHLFHCIUOT-NPBIGWJUSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 216.98 ChemAxon polarizability 89.46 ChemAxon rotatable_bond_count 39 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(16:0/16:1(9Z)) SMP0080515 Phosphatidylethanolamine Biosynthesis PE(16:0/16:1(9Z)) SMP0082318 Specdb::MsMs 563992 Specdb::MsMs 563993 Specdb::MsMs 563994 Specdb::MsMs 2384087 Specdb::MsMs 2384088 Specdb::MsMs 2384089 Specdb::MsMs 2432614 Specdb::MsMs 2432615 Specdb::MsMs 2432616 Specdb::MsMs 2919824 Specdb::MsMs 2919825 Specdb::MsMs 2919826 Specdb::MsMs 3058588 Specdb::MsMs 3058589 Specdb::MsMs 3058590 Specdb::MsMs 3108050 Specdb::MsMs 3108051 Specdb::MsMs 3108052 Specdb::NmrOneD 321891 Specdb::NmrOneD 321892 Specdb::NmrOneD 321893 Specdb::NmrOneD 321894 Specdb::NmrOneD 321895 Specdb::NmrOneD 321896 Specdb::NmrOneD 321897 Specdb::NmrOneD 321898 Specdb::NmrOneD 321899 Specdb::NmrOneD 321900 Specdb::NmrOneD 321901 Specdb::NmrOneD 321902 Specdb::NmrOneD 321903 Specdb::NmrOneD 321904 Specdb::NmrOneD 321905 Specdb::NmrOneD 321906 Specdb::NmrOneD 321907 Specdb::NmrOneD 321908 Specdb::NmrOneD 321909 Specdb::NmrOneD 321910 All Tissues 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 Milk 3.51 +/- 0.03 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 4.2 +/- 0.1 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 5.2 +/- 0.1 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 3.18 +/- 0.02 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 6443788 74000 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP02841 Phosphatidylserine synthase 1 Q2KHY9 PTDSS1 Enzyme