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Identification
YMDB IDYMDB00309
NameGlycerophosphocholine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGlycerophosphocholine, also known as GPC or choline alfoscerate, belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position. Glycerophosphocholine is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • 2-[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-Ethanaminium inner salt
  • a-Glycerophosphorylcholine
  • a-Glycerylphosphorylcholine
  • alpha-Glycerophosphorylcholine
  • alpha-Glycerylphosphorylcholine
  • Choline Alfoscerate
  • Choline glycerophosphate
  • Glycerol 3-phosphocholine
  • Glycerol phosphorylcholine
  • Glycerol-3-phosphatidylcholine
  • Glycerophosphatidylcholine
  • Glycerophosphocholine
  • Glycerophosphorylcholine
  • GPC
  • GPCho
  • hydrogen glycerophosphate Choline
  • L-alpha-Glycerophosphocholine
  • L-alpha-Glycerophosphorylcholine
  • L-alpha-Glycerylphosphorylcholine
  • L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner salt
  • sn-Glycero-3-phosphocholine
  • Alfoscerate, choline
  • Choline alphoscerate
  • Glycerophosphate, choline
  • Alphoscerate, choline
  • L alpha Glycerylphosphorylcholine
  • 3-Phosphocholine, glycerol
  • Glycerol 3 phosphocholine
  • Glycerylphosphorylcholine
CAS number28319-77-9
WeightAverage: 257.2213
Monoisotopic: 257.102823889
InChI KeySUHOQUVVVLNYQR-QMMMGPOBSA-N
InChIInChI=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/t8-/m0/s1
IUPAC Name(2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC NameAlpha-GPC
Chemical FormulaC8H20NO6P
SMILES[H]OC([H])([H])[C@]([H])(O[H])C([H])([H])OP([O-])(=O)OC([H])([H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
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
  • Organic salt
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting point142.5 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility8.96 g/LALOGPS
logP-2.6ALOGPS
logP-5.7ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.05 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity68.68 m³·mol⁻¹ChemAxon
Polarizability24.42 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • extracellular
  • cell envelope
  • endoplasmic reticulum
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Choline metabolismPW002494 ThumbThumb?image type=greyscaleThumb?image type=simple
Ether lipid metabolismPW002492 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ERPW002532 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(10:0/10:0)PW002780 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Ether lipid metabolismec00565 Map00565
Glycerophospholipid metabolismec00564 Map00564
SMPDB Reactions
PC(16:0/16:0) + waterGlycerophosphocholine + hydron + Palmitic acid
PC(14:0/0:0) + waterGlycerophosphocholine + a carboxylate
PC(16:0/0:0) + waterGlycerophosphocholine + a carboxylate
LysoPC(10:0) + waterGlycerophosphocholine + a carboxylate
PC(16:1(9Z)/0:0) + waterGlycerophosphocholine + a carboxylate
KEGG Reactions
water + GlycerophosphocholineGlycerol 3-phosphate + Choline + hydron
hydron + Glycerophosphocholine + fatty acid ↔ 1-O-acylglycerophosphocholine + water
fatty acid + hydron + Glycerophosphocholinewater + phosphatidylcholine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
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.
External Links:
ResourceLink
CHEBI ID16870
HMDB IDHMDB00086
Pubchem Compound ID439285
Kegg IDC00670
ChemSpider ID64931
FOODB IDFDB021802
WikipediaGlycerophosphocholine
BioCyc IDGLYCERYLPHOSPHORYLCHOLINE

Enzymes

General function:
Involved in protein binding
Specific function:
Glycerophosphocholine glycerophosphodiesterase responsible for the hydrolysis of intracellular glycerophosphocholine into glycerol-phosphate and choline. The choline is used for phosphatidyl-choline synthesis. Required for utilization of glycerophosphocholine as phosphate source
Gene Name:
GDE1
Uniprot ID:
Q02979
Molecular weight:
138013.0
Reactions
A glycerophosphodiester + H(2)O → an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Probable glycerophosphocholine glycerophosphodiesterase which may be responsible for the hydrolysis of intracellular glycerophosphocholine into glycerol-phosphate and choline. The choline is used for phosphatidyl-choline synthesis
Gene Name:
Not Available
Uniprot ID:
Q08959
Molecular weight:
37069.39844
Reactions
A glycerophosphodiester + H(2)O → an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in metabolic process
Specific function:
Sequentially removes both fatty acyl groups from diacylglycerophospholipids and therefore has both phospholipase A and lysophospholipase activities. Substrate preference is phosphatidylserine > phosphatidylinositol. Does not cleave phosphatidylcholine, phosphatidylethanolamine, phosphatidic acid and phosphatidylinositol-bisphosphate
Gene Name:
PLB3
Uniprot ID:
Q08108
Molecular weight:
75076.20313
Reactions
2-lysophosphatidylcholine + H(2)O → glycerophosphocholine + a carboxylate.
General function:
Involved in metabolic process
Specific function:
Sequentially removes both fatty acyl groups from diacylglycerophospholipids and therefore has both phospholipase A and lysophospholipase activities. Substrate preference is phosphatidylserine > phosphatidylinositol >> phosphatidylcholine > phosphatidylethanolamine
Gene Name:
PLB1
Uniprot ID:
P39105
Molecular weight:
71666.60156
Reactions
2-lysophosphatidylcholine + H(2)O → glycerophosphocholine + a carboxylate.
General function:
Involved in metabolic process
Specific function:
Intracellular phospholipase B that catalyzes the double deacylation of phosphatidylcholine (PC) to glycerophosphocholine (GroPCho). Plays an important role in membrane lipid homeostasis. Responsible for the rapid PC turnover in response to inositol, elevated temperatures, or when choline is present in the growth medium
Gene Name:
NTE1
Uniprot ID:
Q04958
Molecular weight:
187131.0
Reactions
2-lysophosphatidylcholine + H(2)O → glycerophosphocholine + a carboxylate.
General function:
Involved in metabolic process
Specific function:
Sequentially removes both fatty acyl groups from diacylglycerophospholipids and therefore has both phospholipase A and lysophospholipase activities. Substrate preference is phosphatidylserine > phosphatidylinositol > phosphatidylcholine > phosphatidylethanolamine
Gene Name:
PLB2
Uniprot ID:
Q03674
Molecular weight:
75454.60156
Reactions
2-lysophosphatidylcholine + H(2)O → glycerophosphocholine + a carboxylate.