2.02015-09-08 17:50:23 -06002015-09-14 16:46:01 -0600ECMDB24248M2MDB006365sn-glycero-3-phosphocholinesn-Glycero-3-phosphocholine (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)C8H20NO6P257.2213257.102823889(2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazaniumAlpha-GPCC[N+](C)(C)CCOP([O-])(=O)OCC(O)COInChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3SUHOQUVVVLNYQR-UHFFFAOYSA-Nlogp-2.56logs-1.54solubility8.96e+00 g/llogp-5.7pka_strongest_acidic1.86pka_strongest_basic-3iupac(2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazaniumaverage_mass257.2213mono_mass257.102823889smilesC[N+](C)(C)CCOP([O-])(=O)OCC(O)COformulaC8H20NO6PinchiInChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3inchikeySUHOQUVVVLNYQR-UHFFFAOYSA-Npolar_surface_area99.05refractivity68.68polarizability24.42rotatable_bond_count8acceptor_count4donor_count2physiological_charge0formal_charge0glycerol metabolism IIGlycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through sn-glycero-3-phosphocholine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.PW000915MetabolicSpecdb::CMs2794Specdb::CMs37287Specdb::MsMs297766Specdb::MsMs297767Specdb::MsMs297768Specdb::MsMs339382Specdb::MsMs339383Specdb::MsMs339384Glycerophosphoryl diester phosphodiesteraseP09394GLPQ_ECOLIglpQhttp://ecmdb.ca/proteins/P09394.xmlGlycerophosphoryl diester phosphodiesterase_P10908UGPQ_ECOLIugpQhttp://ecmdb.ca/proteins/P10908.xmlsn-glycero-3-phosphocholine + Water > Hydrogen ion + Benzyl alcohol + Glycerol 3-phosphatePW_R003444