2.0 2012-05-31 09:57:00 -0600 2015-09-13 12:56:06 -0600 ECMDB00086 M2MDB000032 Glycerophosphocholine Glycerophosphorylcholine (GPC) is a choline derivative and one of the two major forms of choline storage (along with phosphocholine) in the cytosol. Glycerophosphorylcholine is also osmolyte. GPC is an intermediate of glycerophospholipid metabolism. It is converted from both 2-acyl-sn-glycero-3-phosphocholine and 1-acyl-sn-glycero-3-phosphocholine by lysophospholipase L2 (EC:3.1.1.5). It is converted to choline and sn-glycerol 3-phosphate by glycerophosphodiester phosphodiesterase (EC:3.1.4.46). (KEGG) 2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-Ethanaminium inner salt <i>sn</i>-3-GPC <i>sn</i>-glycero-3-phosphocholine A-Glycerophosphorylcholine A-Glycerylphosphorylcholine Alpha-Glycerophosphorylcholine Alpha-Glycerylphosphorylcholine Choline Alfoscerate Choline Alfosceric acid Choline glycerophosphate Choline glycerophosphoric acid Glycero-phosphocholine Glycerol 3-phosphocholine Glycerol phosphorylcholine Glycerol-3-phosphatidylcholine Glycerophosphatidylcholine Glycerophosphocholine Glycerophosphorylcholine GPC GPCho Hydrogen glycerophosphate Choline Hydrogen glycerophosphoric acid choline L-1-Glycero-phosphorylcholine L-a-Glycerophosphocholine L-a-Glycerophosphorylcholine L-a-Glycerylphosphorylcholine L-alpha-Glycerophosphocholine L-alpha-Glycerophosphorylcholine L-alpha-Glycerylphosphorylcholine L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner salt L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphoric acid inner salt L-α-Glycerophosphocholine L-α-Glycerophosphorylcholine L-α-Glycerylphosphorylcholine Sn-3-GPC Sn-Glycero-3-phosphocholine α-Glycerophosphorylcholine α-Glycerylphosphorylcholine C8H21NO6P 258.2292 258.110648921 [(2R)-2,3-dihydroxypropoxy][2-(trimethylazaniumyl)ethoxy]phosphinic acid glycerylphosphorylcholine 28319-77-9 C[N+](C)(C)CCO[P@](O)(=O)OC[C@H](O)CO InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/p+1/t8-/m1/s1 SUHOQUVVVLNYQR-MRVPVSSYSA-O Solid Cytosol Extra-organism Periplasm logp -2.46 ALOGPS logs -1.86 ALOGPS solubility 4.04e+00 g/l ALOGPS melting_point 142.5 oC logp -5.7 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2R)-2,3-dihydroxypropoxy][2-(trimethylazaniumyl)ethoxy]phosphinic acid ChemAxon average_mass 258.2292 ChemAxon mono_mass 258.110648921 ChemAxon smiles C[N+](C)(C)CCO[P@](O)(=O)OC[C@H](O)CO ChemAxon formula C8H21NO6P ChemAxon inchi InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/p+1/t8-/m1/s1 ChemAxon inchikey SUHOQUVVVLNYQR-MRVPVSSYSA-O ChemAxon polar_surface_area 96.22 ChemAxon refractivity 69.8 ChemAxon polarizability 25.11 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 1 ChemAxon Glycerophospholipid metabolism ec00564 Biosynthesis of unsaturated fatty acids ec01040 phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::CMs 2508 Specdb::MsMs 1250299 Specdb::MsMs 1250300 Specdb::MsMs 1250301 HMDB00086 439285 64931 C00670 16870 L-1-GLYCERO-PHOSPHORYLCHOLINE CH5 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Evans, Christopher Thomas; McCague, Raymond; Tyrrell, Nicholas David. Preparation of phospholipid-intermediate glycerophosphocholine by a crystallization process. PCT Int. Appl. (1993), 8 pp. http://hmdb.ca/system/metabolites/msds/000/000/061/original/HMDB00086.pdf?1358461515 Lysophospholipase L2 P07000 PLDB_ECOLI pldB http://ecmdb.ca/proteins/P07000.xml Glycerophosphoryl diester phosphodiesterase P09394 GLPQ_ECOLI glpQ http://ecmdb.ca/proteins/P09394.xml Acyl-CoA thioesterase I P0ADA1 TESA_ECOLI tesA http://ecmdb.ca/proteins/P0ADA1.xml sn-glycerol-3-phosphate import ATP-binding protein UgpC P10907 UGPC_ECOLI ugpC http://ecmdb.ca/proteins/P10907.xml Glycerophosphoryl diester phosphodiesterase_ P10908 UGPQ_ECOLI ugpQ http://ecmdb.ca/proteins/P10908.xml sn-glycerol-3-phosphate transport system permease protein ugpA P10905 UGPA_ECOLI ugpA http://ecmdb.ca/proteins/P10905.xml sn-glycerol-3-phosphate transport system permease protein ugpE P10906 UGPE_ECOLI ugpE http://ecmdb.ca/proteins/P10906.xml sn-glycerol-3-phosphate-binding periplasmic protein ugpB P0AG80 UGPB_ECOLI ugpB http://ecmdb.ca/proteins/P0AG80.xml sn-glycerol-3-phosphate import ATP-binding protein UgpC P10907 UGPC_ECOLI ugpC http://ecmdb.ca/proteins/P10907.xml sn-glycerol-3-phosphate transport system permease protein ugpA P10905 UGPA_ECOLI ugpA http://ecmdb.ca/proteins/P10905.xml sn-glycerol-3-phosphate transport system permease protein ugpE P10906 UGPE_ECOLI ugpE http://ecmdb.ca/proteins/P10906.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml sn-glycerol-3-phosphate-binding periplasmic protein ugpB P0AG80 UGPB_ECOLI ugpB http://ecmdb.ca/proteins/P0AG80.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Adenosine triphosphate + Water + Glycerophosphocholine > ADP + Glycerophosphocholine + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Glycerophosphocholine > ADP + Glycerophosphocholine + Hydrogen ion + Phosphate Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion Glycerophosphocholine + Water <> Choline + Glycerol 3-phosphate R01030 2-Acylglycerophosphocholine + Water a carboxylate + Glycerophosphocholine + Hydrogen ion LYSOPHOSPHOLIPASE-RXN 2-lysophosphatidylcholine + Water > Glycerophosphocholine + a carboxylate 1-Acyl-sn-glycero-3-phosphocholine + Water <> Glycerophosphocholine + Carboxylate R07291 Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion 1-Acyl-sn-glycero-3-phosphocholine + Water <> Glycerophosphocholine + Carboxylate Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion 1-Acyl-sn-glycero-3-phosphocholine + Water <> Glycerophosphocholine + Carboxylate