Choline alfoscerate (CHEM034748)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:10:57 UTC
Update Date2016-11-09 01:21:11 UTC
Accession NumberCHEM034748
Identification
Common NameCholine alfoscerate
ClassSmall Molecule
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 exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Glycerophosphocholine exists in all living species, ranging from bacteria to humans. Glycerophosphocholine participates in a number of enzymatic reactions, within cattle. In particular, Glycerophosphocholine can be biosynthesized from 11-cis-retinol and PC(24:1(15Z)/15:0); which is mediated by the enzyme lecithin retinol acyltransferase. In addition, Retinyl ester and glycerophosphocholine can be biosynthesized from vitamin a and PC(24:1(15Z)/15:0) through its interaction with the enzyme lecithin retinol acyltransferase. In cattle, glycerophosphocholine is involved in the metabolic pathway called the retinol metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 FormulaC8H20NO6P
Average Molecular Mass257.221 g/mol
Monoisotopic Mass257.103 g/mol
CAS Registry Number28319-77-9
IUPAC Name(2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
Traditional NameAlpha-GPC
SMILESC[N+](C)(C)CCOP([O-])(=O)OCC(O)CO
InChI IdentifierInChI=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
InChI KeySUHOQUVVVLNYQR-UHFFFAOYSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-7910000000-79a0f6ec434740d09410Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ds-9324000000-3f77ad31e891fc64627eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-9140000000-dfaa66ba1da98fca7ee7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7r-9210000000-dd605c88980d8b4928bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-5b8e226d6d1b7bba9ba2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-4e2ca054587803166774Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kor-2920000000-8d45ca644a1b5ea88a2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-65a218b9f08d2ce2ed9cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000086
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlpha-GPC
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID71920
Kegg Compound IDNot Available
YMDB IDYMDB00309
ECMDB IDECMDB24248
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Evans, Christopher Thomas; McCague, Raymond; Tyrrell, Nicholas David. Preparation of phospholipid-intermediate glycerophosphocholine by a crystallization process. PCT Int. Appl. (1993), 8 pp.
2. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.
3. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.
4. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.
5. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.
6. Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.
7. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.
8. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.
9. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386
10. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)