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Identification
NameGlycerylphosphorylcholine
Accession NumberDB04660
Typesmall molecule
Groupsexperimental
Description

A 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. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
2-{[(2R)-2,3-dihydroxypropoxy](hydroxy)phosphoryloxy}-N,N,N-trimethylethanaminiumNot AvailableNot Available
Choline AlfoscerateNot AvailableNot Available
glycero-3-phosphocholineNot AvailableNot Available
L-alpha-GlycerophosphocholineNot AvailableNot Available
L-alpha-GlycerophosphorylcholineNot AvailableNot Available
L-alpha-GlycerylphosphorylcholineNot AvailableNot Available
SN-glycero-3-phosphocholineNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number563-24-6
WeightAverage: 258.2292
Monoisotopic: 258.110648921
Chemical FormulaC8H21NO6P
InChI KeySUHOQUVVVLNYQR-MRVPVSSYSA-O
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/p+1/t8-/m1/s1
IUPAC Name
[(2R)-2,3-dihydroxypropoxy][2-(trimethylazaniumyl)ethoxy]phosphinic acid
SMILES
C[N+](C)(C)CCO[P@](O)(=O)OC[C@H](O)CO
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassGlycerophospholipids
SubclassGlycerophosphocholines
Direct parentOther Glycerophosphocholines
Alternative parentsPhosphocholines; Monosaccharide Phosphates; Trioses; Organophosphate Esters; Organic Phosphoric Acids; 1,2-Diols; Secondary Alcohols; Primary Alcohols; Polyamines
Substituentsphosphocholine; monosaccharide phosphate; choline; monosaccharide; saccharide; triose monosaccharide; phosphoric acid ester; organic phosphate; secondary alcohol; 1,2-diol; primary alcohol; polyamine; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the other glycerophosphocholines. These are glycerophosphocholines whose structure is based on either of the following skeletons
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.9988
Blood Brain Barrier + 0.567
Caco-2 permeable - 0.5577
P-glycoprotein substrate Substrate 0.6093
P-glycoprotein inhibitor I Non-inhibitor 0.8609
P-glycoprotein inhibitor II Non-inhibitor 0.9342
Renal organic cation transporter Non-inhibitor 0.8826
CYP450 2C9 substrate Non-substrate 0.8492
CYP450 2D6 substrate Non-substrate 0.7639
CYP450 3A4 substrate Substrate 0.517
CYP450 1A2 substrate Non-inhibitor 0.8694
CYP450 2C9 substrate Non-inhibitor 0.8303
CYP450 2D6 substrate Non-inhibitor 0.9125
CYP450 2C19 substrate Non-inhibitor 0.8033
CYP450 3A4 substrate Non-inhibitor 0.8768
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9893
Ames test Non AMES toxic 0.7255
Carcinogenicity Non-carcinogens 0.6032
Biodegradation Ready biodegradable 0.7601
Rat acute toxicity 2.5370 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.5625
hERG inhibition (predictor II) Non-inhibitor 0.7148
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility4.04e+00 g/lALOGPS
logP-2.5ALOGPS
logP-5.7ChemAxon
logS-1.9ALOGPS
pKa (strongest acidic)1.86ChemAxon
pKa (strongest basic)-3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area96.22ChemAxon
rotatable bond count8ChemAxon
refractivity69.8ChemAxon
polarizability25.11ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Carlo Scolastico, Giovanni Tronconi, “Diacyl derivatives of glycerylphosphorylcholine, their preparation, and antihyperlipidemic compositions.” U.S. Patent US4699901, issued October 13, 1987.

US4699901
General Reference
  1. Ferraro L, Tanganelli S, Marani L, Bianchi C, Beani L, Siniscalchi A: Evidence for an in vivo and in vitro modulation of endogenous cortical GABA release by alpha-glycerylphosphorylcholine. Neurochem Res. 1996 May;21(5):547-52. Pubmed
External Links
ResourceLink
KEGG CompoundC00670
PubChem Compound439285
PubChem Substance46508680
ChEBI16870
ChEMBL
HETCH5
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Ganglioside GM2 activator

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Ganglioside GM2 activator P17900 Details
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Drug created on September 11, 2007 11:49 / Updated on September 16, 2013 17:25