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Record Information
Version1.0
Creation Date2016-07-13 19:40:58 UTC
Update Date2016-07-20 20:48:55 UTC
LmdbLMDB00036
Secondary Accession NumbersNone
Metabolite Identification
Common NameGlycerophosphocholine
DescriptionGlycerophosphorylcholine (GPC) is a choline derivative and one of the two major forms of choline storage (along with phosphocholine) in the cytosol. Glycerophosphorylcholine is also one of the four major organic osmolytes in renal medullary cells, changing their intracellular osmolyte concentration in parallel with extracellular tonicity during cellular osmoadaptation. As an osmolyte, Glycerophosphorylcholine counteracts the effects of urea on enzymes and other macromolecules. Kidneys (especially medullar cells), which are exposed under normal physiological conditions to widely fluctuating extracellular solute concentrations, respond to hypertonic stress by accumulating the organic osmolytes glycerophosphorylcholine (GPC), betaine, myo-inositol, sorbitol and free amino acids. Increased intracellular contents of these osmolytes are achieved by a combination of increased uptake (myo-inositol and betaine) and synthesis (sorbitol, GPC), decreased degradation (GPC) and reduced osmolyte release. GPC is formed in the breakdown of phosphatidylcholine (PtC). This pathway is active in many body tissues, including mammary tissue.
Structure
Thumb
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
Choline glycerophosphateHMDB
Glycerol 3-phosphocholineHMDB
Glycerol phosphorylcholineHMDB
Glycerol-3-phosphatidylcholineHMDB
GlycerophosphatidylcholineHMDB
GlycerophosphorylcholineHMDB
GPCHMDB
GPChoHMDB
Hydrogen glycerophosphate cholineHMDB
L-alpha-GlycerophosphocholineHMDB
L-alpha-GlycerophosphorylcholineHMDB
L-alpha-GlycerylphosphorylcholineHMDB
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner saltHMDB
sn-glycero-3-PhosphocholineHMDB
Alfoscerate, cholineMeSH
Choline alphoscerateMeSH
Glycerophosphate, cholineMeSH
Alphoscerate, cholineMeSH
L alpha GlycerylphosphorylcholineMeSH
3-Phosphocholine, glycerolMeSH
Glycerol 3 phosphocholineMeSH
GlycerylphosphorylcholineMeSH
Chemical FormulaC8H20NO6P
Average Molecular Weight257.2213
Monoisotopic Molecular Weight257.102823889
IUPAC Name(2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
Traditional NameAlpha-GPC
CAS Registry Number28319-77-9
SMILES
C[N+](C)(C)CCOP([O-])(=O)OC[C@@H](O)CO
InChI Identifier
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/t8-/m0/s1
InChI KeySUHOQUVVVLNYQR-QMMMGPOBSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Jejunum
  • Kidney
  • Liver
  • Lung
  • Milk
  • Plasma
  • Serum
  • Vitreous Humour
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
JejunumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
KidneyDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LiverDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LungDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified395-1217 uMNot AvailableBovine details
MilkDetected and Quantified284-1460 uMNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
Vitreous HumourDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
DrugBank IDNot Available
HMDB IDHMDB0000086
FooDB IDFDB021802
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID35659
BioCyc IDGLYCERYLPHOSPHORYLCHOLINE
METLIN ID370
PDB IDNot Available
Wikipedia LinkAlpha-GPC
Chemspider ID64931
ChEBI ID16870
PubChem Compound ID71920
Kegg Compound IDC00670
YMDB IDYMDB00309
ECMDB IDECMDB24248
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available