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Identification
NameCholine alfoscerate
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
(2R)-2,3-dihydroxypropyl 2-(trimethylammonio)ethyl phosphate
alpha-Glycerophosphorylcholine
Choline alphoscerate
Choline glycerophosphate
Cholini glycerophosphas
Glicerofosfato de colina
Glycerol phosphorylcholine
Glycerol-3-phosphatidylcholine
glycerol-3-phosphocholine
Glycerophosphate de choline
Glycerophosphocholine
Glycerophosphorylcholine
GPCho
L-alpha-Glycerophosphocholine
L-alpha-Glycerophosphorylcholine
sn-3-GPC
sn-Glycero-3-phosphocholine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII60M22SGW66
CAS number28319-77-9
WeightAverage: 257.223
Monoisotopic: 257.102824366
Chemical FormulaC8H20NO6P
InChI KeySUHOQUVVVLNYQR-MRVPVSSYSA-N
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/t8-/m1/s1
IUPAC Name
(2-{[(2R)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
SMILES
[H][C@@](O)(CO)COP([O-])(=O)OCC[N+](C)(C)C
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
  • Choline
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • 1,2-diol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organic zwitterion
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption-0.9988
Blood Brain Barrier+0.567
Caco-2 permeable-0.5577
P-glycoprotein substrateSubstrate0.6093
P-glycoprotein inhibitor INon-inhibitor0.8609
P-glycoprotein inhibitor IINon-inhibitor0.9342
Renal organic cation transporterNon-inhibitor0.8826
CYP450 2C9 substrateNon-substrate0.8492
CYP450 2D6 substrateNon-substrate0.7639
CYP450 3A4 substrateSubstrate0.517
CYP450 1A2 substrateNon-inhibitor0.8694
CYP450 2C9 inhibitorNon-inhibitor0.8303
CYP450 2D6 inhibitorNon-inhibitor0.9125
CYP450 2C19 inhibitorNon-inhibitor0.8033
CYP450 3A4 inhibitorNon-inhibitor0.8768
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9893
Ames testNon AMES toxic0.7255
CarcinogenicityNon-carcinogens0.6032
BiodegradationReady biodegradable0.7601
Rat acute toxicity2.5370 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5625
hERG inhibition (predictor II)Non-inhibitor0.7148
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.96 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity68.68 m3·mol-1ChemAxon
Polarizability24.74 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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 References
  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:8726961 ]
External Links
ATC CodesN07AX02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Phospholipase activator activity
Specific Function:
The large binding pocket can accommodate several single chain phospholipids and fatty acids, GM2A also exhibits some calcium-independent phospholipase activity (By similarity). Binds gangliosides and stimulates ganglioside GM2 degradation. It stimulates only the breakdown of ganglioside GM2 and glycolipid GA2 by beta-hexosaminidase A. It extracts single GM2 molecules from membranes and presents...
Gene Name:
GM2A
Uniprot ID:
P17900
Molecular Weight:
20838.1 Da
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Drug created on September 11, 2007 11:49 / Updated on April 30, 2016 20:59