Choline alfoscerate

Identification

Name
Choline alfoscerate
Accession Number
DB04660
Type
Small Molecule
Groups
Experimental, Investigational
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
Categories
UNII
60M22SGW66
CAS number
28319-77-9
Weight
Average: 257.223
Monoisotopic: 257.102824366
Chemical Formula
C8H20NO6P
InChI Key
SUHOQUVVVLNYQR-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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGanglioside GM2 activatorNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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
KEGG Drug
D07349
KEGG Compound
C00670
PubChem Compound
657272
PubChem Substance
46508680
ChemSpider
571409
ChEBI
16870
ChEMBL
CHEMBL1567463
HET
CH5
Wikipedia
Alpha-GPC
ATC Codes
N07AX02 — Choline alfoscerate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3RecruitingTreatmentType 2 Diabetes Mellitus1
4CompletedTreatmentCognitive Impairments / Strokes1
4RecruitingTreatmentAlzheimer's Disease (AD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Glycerophospholipids
Sub Class
Glycerophosphocholines
Direct Parent
Glycerophosphocholines
Alternative Parents
Phosphocholines / Dialkyl phosphates / Tetraalkylammonium salts / Secondary alcohols / 1,2-diols / Primary alcohols / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives
show 1 more
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
show 12 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
phosphocholines, sn-glycerol 3-phosphates (CHEBI:16870)

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 a...
Gene Name
GM2A
Uniprot ID
P17900
Uniprot Name
Ganglioside GM2 activator
Molecular Weight
20838.1 Da

Drug created on September 11, 2007 11:49 / Updated on November 02, 2018 06:03