Record Information
Version2.0
Creation Date2012-05-31 09:57:00 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00086
Identification
Name:Glycerophosphocholine
Description: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)
Structure
Thumb
Synonyms:
  • 2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-Ethanaminium inner salt
  • sn-3-GPC
  • sn-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
Chemical Formula:C8H21NO6P
Weight:Average: 258.2292
Monoisotopic: 258.110648921
InChI Key:SUHOQUVVVLNYQR-MRVPVSSYSA-O
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
CAS number:28319-77-9
IUPAC Name:[(2R)-2,3-dihydroxypropoxy][2-(trimethylazaniumyl)ethoxy]phosphinic acid
Traditional IUPAC Name:glycerylphosphorylcholine
SMILES:C[N+](C)(C)CCO[P@](O)(=O)OC[C@H](O)CO
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassGlycerophospholipids
Direct ParentGlycerophosphocholines
Alternative Parents
Substituents
  • Glycero-3-phosphocholine
  • Phosphocholine
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • 1,2-diol
  • Secondary alcohol
  • Organic nitrogen compound
  • Alcohol
  • Organic salt
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:0
Melting point:142.5 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.04 mg/mLALOGPS
logP-2.5ALOGPS
logP-5.7ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity69.8 m3·mol-1ChemAxon
Polarizability25.11 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Biosynthesis of unsaturated fatty acids ec01040
  • Glycerophospholipid metabolism ec00564
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
References
References:
  • 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. Pubmed: 22080510
  • 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. Pubmed: 21097882
  • 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
Synthesis Reference:Evans, Christopher Thomas; McCague, Raymond; Tyrrell, Nicholas David. Preparation of phospholipid-intermediate glycerophosphocholine by a crystallization process. PCT Int. Appl. (1993), 8 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16870
HMDB IDHMDB00086
Pubchem Compound ID439285
Kegg IDC00670
ChemSpider ID64931
Wikipedia IDAlpha-GPC
BioCyc IDL-1-GLYCERO-PHOSPHORYLCHOLINE
EcoCyc IDL-1-GLYCERO-PHOSPHORYLCHOLINE
Ligand ExpoCH5

Enzymes

General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Uniprot ID:
P07000
Molecular weight:
38978
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
glpQ
Uniprot ID:
P09394
Molecular weight:
40843
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:
tesA
Uniprot ID:
P0ADA1
Molecular weight:
23622
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:
ugpC
Uniprot ID:
P10907
Molecular weight:
39524
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
ugpQ
Uniprot ID:
P10908
Molecular weight:
27409
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpA
Uniprot ID:
P10905
Molecular weight:
33264
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpE
Uniprot ID:
P10906
Molecular weight:
31499
General function:
Involved in transporter activity
Specific function:
sn-glycerol-3-phosphate and glycerophosphoryl diester- binding protein interacts with the binding protein-dependent transport system ugpACE
Gene Name:
ugpB
Uniprot ID:
P0AG80
Molecular weight:
48448

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:
ugpC
Uniprot ID:
P10907
Molecular weight:
39524
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpA
Uniprot ID:
P10905
Molecular weight:
33264
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpE
Uniprot ID:
P10906
Molecular weight:
31499
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
sn-glycerol-3-phosphate and glycerophosphoryl diester- binding protein interacts with the binding protein-dependent transport system ugpACE
Gene Name:
ugpB
Uniprot ID:
P0AG80
Molecular weight:
48448
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368