L-1-glycero-3-phosphocholine (CHEM042280)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:57:13 UTC
Update Date2016-11-09 01:22:38 UTC
Accession NumberCHEM042280
Identification
Common NameL-1-glycero-3-phosphocholine
ClassSmall Molecule
DescriptionA component of phosphatidylcholines (lecithins), in which the two hydroxy groups of glycerol are esterified with fatty acids. (From Stedman, 26th ed) It counteracts the effects of urea on enzymes and other macromolecules.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-2,3-Dihydroxypropyl 2-(trimethylammonio)ethyl phosphateChEBI
Alfoscerate de cholineChEBI
Alfoscerato de colinaChEBI
alpha-GlycerophosphorylcholineChEBI
Choline alphoscerateChEBI
Choline glycerophosphateChEBI
Cholini alfoscerasChEBI
Cholini glycerophosphasChEBI
Glicerofosfato de colinaChEBI
Glycerol phosphorylcholineChEBI
Glycerol-3-phosphatidylcholineChEBI
Glycerol-3-phosphocholineChEBI
Glycerophosphate de cholineChEBI
GlycerophosphorylcholineChEBI
GPChoChEBI
L-alpha-GlycerophosphocholineChEBI
L-alpha-GlycerophosphorylcholineChEBI
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner saltChEBI
sn-3-GPCChEBI
sn-Glycero-3-phosphocholineChEBI
sn-Glycerol 3-phosphocholineChEBI
GliatilinKegg
(2R)-2,3-Dihydroxypropyl 2-(trimethylammonio)ethyl phosphoric acidGenerator
Alfosceric acid de cholineGenerator
a-GlycerophosphorylcholineGenerator
Α-glycerophosphorylcholineGenerator
Choline alphosceric acidGenerator
Choline glycerophosphoric acidGenerator
Glycerophosphoric acid de cholineGenerator
L-a-GlycerophosphocholineGenerator
L-Α-glycerophosphocholineGenerator
L-a-GlycerophosphorylcholineGenerator
L-Α-glycerophosphorylcholineGenerator
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphoric acid inner saltGenerator
Choline alfosceric acidHMDB
Glycerol 3 phosphocholineHMDB
GlycerylphosphorylcholineHMDB
Alphoscerate, cholineHMDB
L alpha GlycerylphosphorylcholineHMDB
3-Phosphocholine, glycerolHMDB
Glycerol 3-phosphocholineHMDB
L-alpha-GlycerylphosphorylcholineHMDB
Alfoscerate, cholineHMDB
Glycerophosphate, cholineHMDB
2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium inner saltHMDB
a-GlycerylphosphorylcholineHMDB
alpha-GlycerylphosphorylcholineHMDB
Choline alfoscerateHMDB
GlycerophosphatidylcholineHMDB
GPCHMDB
Hydrogen glycerophosphate cholineHMDB
CeretonHMDB
CholicerinHMDB
CholitilineHMDB
DelecitHMDB
Glycerol 3-phosphorylcholineHMDB
Glycerophosphoric acid choline esterHMDB
Glyceryl 3-phosphorylcholineHMDB
GlycerylphosphocholineHMDB
L-alpha-GPCHMDB
L-Α-GPCHMDB
L-Α-glycerylphosphorylcholineHMDB
O-(sn-Glycero-3-phosphoryl)-cholineHMDB
sn-Glycero-3-phosphorylcholineHMDB
Α-glycerylphosphorylcholineHMDB
GlycerophosphocholineChEBI
Chemical FormulaC8H20NO6P
Average Molecular Mass257.223 g/mol
Monoisotopic Mass257.103 g/mol
CAS Registry NumberNot Available
IUPAC Name(2-{[(2R)-2,3-dihydroxypropyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2,3-dihydroxypropyl phosphono]oxy}ethyl)trimethylazanium
SMILES[H][C@@](O)(CO)COP([O-])(=O)OCC[N+](C)(C)C
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/t8-/m1/s1
InChI KeySUHOQUVVVLNYQR-MRVPVSSYSA-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 Descriptors
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
Polarizability24.77 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 (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-9310000000-e2633e56c86952054710Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1690000000-53ffc11b39ba8f89f803Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d4d2c5d7e0856e948624Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-848201d8ac3bd454c67aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-01w1-9300000000-987e5431e2d611fa5032Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2490000000-efb55f1ddbed9f1a8754Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-df7b0a6ce3c788063f53Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0960000000-7df186ffc569be161b39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-9140000000-3347b58fbc5fe0b0a201Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7r-9210000000-60118aed826a14bb4cb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-b6ac875e42841f04bcfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-9adc870a20cd016e3aa2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kor-2920000000-b31eb4ca99ba45d9f931Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-dec05a487d7ae73f1d27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-bd45c4f9a61bbdbbd2d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3960000000-2d618fc6f1a9c434909cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0960000000-782cafcc84f2e1b58561Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-5fbae562ef71fe1bd552Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-9800000000-00d2deed17b9ac0f5789Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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 IDDB04660
HMDB IDHMDB0000086
FooDB IDFDB030952
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDL-1-GLYCERO-PHOSPHORYLCHOLINE
METLIN ID370
PDB IDNot Available
Wikipedia LinkAlpha-GPC
Chemspider ID571409
ChEBI ID16870
PubChem Compound ID657272
Kegg Compound IDC00670
YMDB IDNot Available
ECMDB IDNot Available
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. Satlin A, Bodick N, Offen WW, Renshaw PF: Brain proton magnetic resonance spectroscopy (1H-MRS) in Alzheimer's disease: changes after treatment with xanomeline, an M1 selective cholinergic agonist. Am J Psychiatry. 1997 Oct;154(10):1459-61.
3. Walter A, Korth U, Hilgert M, Hartmann J, Weichel O, Hilgert M, Fassbender K, Schmitt A, Klein J: Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Neurobiol Aging. 2004 Nov-Dec;25(10):1299-303.
4. Theberge J, Al-Semaan Y, Jensen JE, Williamson PC, Neufeld RW, Menon RS, Schaefer B, Densmore M, Drost DJ: Comparative study of proton and phosphorus magnetic resonance spectroscopy in schizophrenia at 4 Tesla. Psychiatry Res. 2004 Nov 15;132(1):33-9.
5. Miller BL, Lin KM, Djenderedjian A, Tang C, Hill E, Fu P, Nuccio C, Jenden DJ: Changes in red blood cell choline and choline-bound lipids with oral lithium. Experientia. 1990 May 15;46(5):454-6.
6. Caetano SC, Fonseca M, Olvera RL, Nicoletti M, Hatch JP, Stanley JA, Hunter K, Lafer B, Pliszka SR, Soares JC: Proton spectroscopy study of the left dorsolateral prefrontal cortex in pediatric depressed patients. Neurosci Lett. 2005 Aug 26;384(3):321-6.
7. Nitsch R, Pittas A, Blusztajn JK, Slack BE, Growdon JH, Wurtman RJ: Alterations of phospholipid metabolites in postmortem brain from patients with Alzheimer's disease. Ann N Y Acad Sci. 1991;640:110-3.
8. Chap HJ, Moatti JP, Mieusset R, Nieto M, Laneelle G, Bennet PJ, Mansat A, Pontonnier F, Douste-Blazy L: Simple, rapid enzymatic determination of glycerophosphocholine in human seminal plasma. Clin Chem. 1988 Jan;34(1):106-9.
9. Blusztajn JK, Lopez Gonzalez-Coviella I, Logue M, Growdon JH, Wurtman RJ: Levels of phospholipid catabolic intermediates, glycerophosphocholine and glycerophosphoethanolamine, are elevated in brains of Alzheimer's disease but not of Down's syndrome patients. Brain Res. 1990 Dec 17;536(1-2):240-4.
10. Mandal PK, McClure RJ, Pettegrew JW: Interactions of Abeta(1-40) with glycerophosphocholine and intact erythrocyte membranes: fluorescence and circular dichroism studies. Neurochem Res. 2004 Dec;29(12):2273-9.
11. Pomfret EA, daCosta KA, Schurman LL, Zeisel SH: Measurement of choline and choline metabolite concentrations using high-pressure liquid chromatography and gas chromatography-mass spectrometry. Anal Biochem. 1989 Jul;180(1):85-90.
12. Nitsch RM, Blusztajn JK, Pittas AG, Slack BE, Growdon JH, Wurtman RJ: Evidence for a membrane defect in Alzheimer disease brain. Proc Natl Acad Sci U S A. 1992 Mar 1;89(5):1671-5.
13. Miller BL, Read S, Tang C, Jenden D: Differences in red blood cell choline and lipid-bound choline between patients with Alzheimer disease and control subjects. Neurobiol Aging. 1991 Jan-Feb;12(1):61-4.
14. Jensen JE, Drost DJ, Menon RS, Williamson PC: In vivo brain (31)P-MRS: measuring the phospholipid resonances at 4 Tesla from small voxels. NMR Biomed. 2002 Aug;15(5):338-47.
15. Zhang Q, Southall MD, Mezsick SM, Johnson C, Murphy RC, Konger RL, Travers JB: Epidermal peroxisome proliferator-activated receptor gamma as a target for ultraviolet B radiation. J Biol Chem. 2005 Jan 7;280(1):73-9. Epub 2004 Oct 29.
16. Fallbrook A, Turenne SD, Mamalias N, Kish SJ, Ross BM: Phosphatidylcholine and phosphatidylethanolamine metabolites may regulate brain phospholipid catabolism via inhibition of lysophospholipase activity. Brain Res. 1999 Jul 10;834(1-2):207-10.
17. Blank ML, Smith ZL, Fitzgerald V, Snyder F: The CoA-independent transacylase in PAF biosynthesis: tissue distribution and molecular species selectivity. Biochim Biophys Acta. 1995 Feb 9;1254(3):295-301.
18. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
19. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
20. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
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