sn-glycero-3-phosphocholine (ECMDB24248) (M2MDB006365)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2015-09-08 17:50:23 -0600
Update Date2015-09-14 16:46:01 -0600
Secondary Accession Numbers
  • ECMDB24248
Identification
Name:sn-glycero-3-phosphocholine
Descriptionsn-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)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium inner saltHMDB
a-GlycerophosphorylcholineHMDB
a-GlycerylphosphorylcholineHMDB
alpha-GlycerophosphorylcholineHMDB
alpha-GlycerylphosphorylcholineHMDB
Choline alfoscerateHMDB, MeSH
Choline glycerophosphateHMDB
Glycerol 3-phosphocholineHMDB, MeSH
Glycerol phosphorylcholineHMDB
Glycerol-3-phosphatidylcholineHMDB
GlycerophosphatidylcholineHMDB
GlycerophosphorylcholineHMDB, MeSH
GPCHMDB
GPChoHMDB
Hydrogen glycerophosphate cholineHMDB
L-alpha-GlycerophosphocholineHMDB
L-alpha-GlycerophosphorylcholineHMDB
L-alpha-GlycerylphosphorylcholineHMDB, MeSH
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner saltHMDB
sn-glycero-3-PhosphocholineHMDB
Alfoscerate, cholineMeSH, HMDB
Choline alphoscerateMeSH, HMDB
Glycerophosphate, cholineMeSH, HMDB
Alphoscerate, cholineMeSH, HMDB
L alpha GlycerylphosphorylcholineMeSH, HMDB
3-Phosphocholine, glycerolMeSH, HMDB
Glycerol 3 phosphocholineMeSH, HMDB
GlycerylphosphorylcholineMeSH, HMDB
CeretonHMDB
CholicerinHMDB
CholitilineHMDB
DelecitHMDB
GliatilinHMDB
Glycerol 3-phosphorylcholineHMDB
GlycerophosphocholineHMDB
Glycerophosphoric acid choline esterHMDB
Glyceryl 3-phosphorylcholineHMDB
GlycerylphosphocholineHMDB
L-alpha-GPCHMDB
L-α-GPCHMDB
L-α-GlycerophosphocholineHMDB
L-α-GlycerophosphorylcholineHMDB
L-α-GlycerylphosphorylcholineHMDB
O-(sn-glycero-3-Phosphoryl)-cholineHMDB
sn-glycero-3-PhosphorylcholineHMDB
α-GlycerophosphorylcholineHMDB
α-GlycerylphosphorylcholineHMDB
Chemical Formula:C8H20NO6P
Weight:Average: 257.2213
Monoisotopic: 257.102823889
InChI Key:SUHOQUVVVLNYQR-UHFFFAOYSA-N
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
CAS number:Not Available
IUPAC Name:(2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Name:Alpha-GPC
SMILES:C[N+](C)(C)CCOP([O-])(=O)OCC(O)CO
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
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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:Cytoplasm
Reactions:
sn-glycero-3-phosphocholine + Water > Hydrogen ion + Benzyl alcohol + Glycerol 3-phosphate
SMPDB Pathways:
glycerol metabolism IIPW000915 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-7910000000-79a0f6ec434740d09410View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ds-9324000000-3f77ad31e891fc64627eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-9140000000-dfaa66ba1da98fca7ee7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7r-9210000000-dd605c88980d8b4928bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-5b8e226d6d1b7bba9ba2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-4e2ca054587803166774View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kor-2920000000-8d45ca644a1b5ea88a2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-65a218b9f08d2ce2ed9cView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0000086
Pubchem Compound ID71920
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDAlpha-GPC
BioCyc IDNot Available

Enzymes

Protein Details
1. Glycerophosphoryl diester phosphodiesterase
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.
Protein Details
2. Glycerophosphoryl diester phosphodiesterase_
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.