2.0 2015-09-08 17:50:23 -0600 2015-09-14 16:46:01 -0600 ECMDB24248 M2MDB006365 sn-glycero-3-phosphocholine sn-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) C8H20NO6P 257.2213 257.102823889 (2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium Alpha-GPC C[N+](C)(C)CCOP([O-])(=O)OCC(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 SUHOQUVVVLNYQR-UHFFFAOYSA-N logp -2.56 ALOGPS logs -1.54 ALOGPS solubility 8.96e+00 g/l ALOGPS logp -5.7 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 257.2213 ChemAxon mono_mass 257.102823889 ChemAxon smiles C[N+](C)(C)CCOP([O-])(=O)OCC(O)CO ChemAxon formula C8H20NO6P 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 ChemAxon inchikey SUHOQUVVVLNYQR-UHFFFAOYSA-N ChemAxon polar_surface_area 99.05 ChemAxon refractivity 68.68 ChemAxon polarizability 24.42 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon glycerol metabolism II Glycerol 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. PW000915 Metabolic Specdb::CMs 2794 Specdb::CMs 37287 Specdb::MsMs 297766 Specdb::MsMs 297767 Specdb::MsMs 297768 Specdb::MsMs 339382 Specdb::MsMs 339383 Specdb::MsMs 339384 Glycerophosphoryl diester phosphodiesterase P09394 GLPQ_ECOLI glpQ http://ecmdb.ca/proteins/P09394.xml Glycerophosphoryl diester phosphodiesterase_ P10908 UGPQ_ECOLI ugpQ http://ecmdb.ca/proteins/P10908.xml sn-glycero-3-phosphocholine + Water > Hydrogen ion + Benzyl alcohol + Glycerol 3-phosphate PW_R003444