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Showing Compound Choline alfoscerate (FDB021802)

Record Information
Version1.0
Creation date2011-04-11 15:42:27 UTC
Update date2015-10-09 22:31:27 UTC
Primary IDFDB021802
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCholine alfoscerate
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. [HMDB]
CAS Number28319-77-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Choline alfosceric acidGenerator
Glycerophosphate, cholineMeSH
Alphoscerate, cholineMeSH
Choline glycerophosphateMeSH
Glycerol 3 phosphocholineMeSH
3-Phosphocholine, glycerolMeSH
GlycerophosphorylcholineMeSH
L alpha GlycerylphosphorylcholineMeSH
Glycerol 3-phosphocholineMeSH
Choline alphoscerateMeSH
Alfoscerate, cholineMeSH
L-alpha-GlycerylphosphorylcholineMeSH
(R)-Glycerylphosphorylcholinemanual
2-[[(2,3-Dihydroxypropoxy)hydroxyinyl]oxy]-N,N,N-trimethyl-ethanaminium inner saltHMDB
a-GlyceroOrylcholineHMDB
a-GlycerylorylcholineHMDB
alpha-GlyceroOrylcholineHMDB
alpha-GlycerylorylcholineHMDB
Choline alfosceratemanual
Choline alfoscerate, INNdb_source
Choline glyceroateHMDB
GlyceroAtidylcholineHMDB
Glycerol 3-ocholineHMDB
Glycerol orylcholineHMDB
Glycerol-3-atidylcholineHMDB
GlyceroOcholineHMDB
GlyceroOrylcholineHMDB
GPCHMDB
GPChoHMDB
Hydrogen glyceroate cholineHMDB
L-alpha-GlyceroOcholineHMDB
L-alpha-GlyceroOrylcholineHMDB
L-alpha-GlycerylorylcholineHMDB
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen ate inner saltHMDB
sn-glycero-3-OcholineHMDB
sn-Glycero-3-phosphocholinedb_source
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
Polarizability24.82 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H20NO6P
IUPAC name{2-[(2,3-dihydroxypropyl phosphono)oxy]ethyl}trimethylazanium
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
Isomeric SMILESC[N+](C)(C)CCOP([O-])(=O)OCC(O)CO
Average Molecular Weight257.2213
Monoisotopic Molecular Weight257.102823889
Classification
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 Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCholine alfoscerate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03la-9620000000-b364be629483f7a773d9Spectrum
Predicted GC-MSCholine alfoscerate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCholine alfoscerate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCholine alfoscerate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCholine alfoscerate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCholine alfoscerate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCholine alfoscerate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCholine alfoscerate, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MSNot Available
NMRNot Available
ChemSpider ID64931
ChEMBL IDNot Available
KEGG Compound IDC00670
Pubchem Compound ID71920
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00086
CRC / DFC (Dictionary of Food Compounds) IDDYC98-J:DYJ34-W
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35659
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Ectonucleotide pyrophosphatase/phosphodiesterase family member 6ENPP6Q6UWR7
60 kDa lysophospholipaseASPGQ86U10
Galactoside-binding soluble lectin 13LGALS13Q9UHV8
Eosinophil lysophospholipaseCLCQ05315
Neuropathy target esterasePNPLA6Q8IY17
Acyl-protein thioesterase 1LYPLA1O75608
Acyl-protein thioesterase 2LYPLA2O95372
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference