CAS 563-24-6|CAS 28319-77-9|(2-{[(S)-((2R)-2,3-dihydroxypropyl phosphonato)]oxy}ethyl)trimethylazanium|Glycerylphosphorylcholine|2-{[(2R)-2,3-dihydroxypropoxy](hydroxy)phosphoryloxy}-N,N,N-trimethyl...

General Information

Structure

Molecular Formula

C₈H₂₀NO₆P

Molecular Mass

257.221261

Exact Mass

257.102824

Charge

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

InChIKey

SUHOQUVVVLNYQR-MRVPVSSYSA-N

Canonic Smiles

OC[C@H](COP(=O)(OCC[N+](C)(C)C)[O-])O

Isomeric Smiles

C[N+](C)(C)CCOP(=O)([O-])OC[C@H](O)CO

Calculated Properties

JChem

LogD (pH = 7.4)

-3.70

LogD (pH = 5.5)

-3.70

Log P

-5.73

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

1.86

Polar Surface Area

99.05

Polarizability

24.77

Molar Refractivity

68.68

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC Traditional name

(2-{[(S)-((2R)-2,3-dihydroxypropyl phosphonato)]oxy}ethyl)trimethylazanium α-gpc Alpha-GPC

Synonyms

Glycerylphosphorylcholine2-{[(2R)-2,3-dihydroxypropoxy](hydroxy)phosphoryloxy}-N,N,N-trimethylethanaminiumL-alpha-GlycerylphosphorylcholineGPCL-alpha-GlycerophosphorylcholineCholine AlfoscerateSN-glycero-3-phosphocholineglycero-3-phosphocholineL-alpha-GlycerophosphocholineL-α-GPCO-(sn-glycero-3-Phosphoryl)cholineCholitilineDelecitCeretonSn-Glycerophosphocholine2-[[[(2R)-2,3-Dihydroxypropoxy]hydroxyphosphinyl]oxy]-N,N,N-trimethylethanaminium Inner SaltL-α-Glycerophosphorylcholinesn-Glycero-3-phosphorylcholineL-α-GlycerylphosphorylcholineGlycerylphosphocholineBrezalL-α-GlycerophosphocholineGlycerylphosphorylcholineCholicerinα-Glycerylphosphorylcholinesn-Glycero-3-phosphocholineα-Glycerophosphorylcholinecholine alfosceratesn-glycerol 3-phosphocholinealpha-Glycerophosphorylcholineglycerol-3-phosphocholine(2R)-2,3-dihydroxypropyl 2-(trimethylammonio)ethyl phosphateGlycerophosphocholineGPChosn-Glycero-3-phosphocholineGlycerol phosphorylcholineGlycerophosphorylcholineL-alpha-GlycerophosphorylcholineCholine alphosceratesn-glycero-3-phosphocholineGlicerofosfato de colinaCholine glycerophosphateL-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner saltL-alpha-GlycerophosphocholineGlycerophosphate de cholinesn-3-GPCGlycerol-3-phosphatidylcholineCholini glycerophosphas

IUPAC name

(2-{[(S)-((2R)-2,3-dihydroxypropyl phosphonato)]oxy}ethyl)trimethylazanium (2-{[(2R)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium

International Nonproprietary Name (INN)

alfoscerato de colinacholine alfosceratecholini alfoscerasalfoscerate de choline

Names and Identifiers

Registration numbers

PubChem CID

439285657272

CAS Number

563-24-628319-77-9

PubChem SID

465086801609676528145747

UniProt Database

P02786Q9P327Q2A069P18141P47713Q5RDS0B3NY03Q6UWR7Q90037Q9USJ4P07000P08669B2C4J0Q21407O77793

SureChEMBL Database

SCHEMBL63754

PubMed Citation Links

22191561241562632331455223387341235284932119543323013274211653962326825864204662295928322679745226777512324443224166560

KEGG ID

C00670

CHEMBL

CHEMBL1567463

MetaCyc Database

L-1-GLYCERO-PHOSPHORYLCHOLINE

IntEnz Database

EC 3.1.4.2EC 3.3.2.2EC 3.1.4.38EC 3.1.1.5

EnzymePortal Database

Q9P327Q9U969Q4PF83O13857B4JLX2Q6UWR7O88202Q05017B0XZV8Q5RB45Q86U10A2R350O42790B4N1W9Q2UDH2

Reactom Database

R-HSA-1482685R-HSA-1482612R-HSA-6814766R-HSA-8952251R-HSA-6814132R-HSA-6814254R-HSA-1483116R-HSA-8847912R-HSA-6814778R-HSA-1482629R-HSA-1482696

Rhea Database

RHEA:16061RHEA:41352RHEA:63772RHEA:19545RHEA:58460RHEA:63656RHEA:40975RHEA:40807RHEA:58476RHEA:22544RHEA:56236RHEA:56164RHEA:40827RHEA:40835RHEA:40887RHEA:44696

CHEBI ID

CHEBI:12847CHEBI:55397CHEBI:41458CHEBI:26697CHEBI:14343CHEBI:16870CHEBI:10646CHEBI:12841CHEBI:76433

Reaxys Registry

KEGG DRUG Database

ACToR Database

SABIO-RK Database

Patent number

GB2057872EP1992322WO2007124465

HMDB Database

HMDB0000086

VirtualMetabolicHuman Database

g3pc

IntAct Database

EBI-8874564

Wikipedia Title

Alpha-GPC

Drug Central Database

PDBeChem Database

DrugBank ID

Beilstein Number

Registration numbers

Properties

Physical Property

Melting Point

130-134°C

Solubility

Methanol

Apperance

White Solid

Safety Information

Storage Condition

Hygroscopic, -20°C Freezer, Under Inert Atmosphere

MSDS Link

Download link

Product Information

Certificate of Analysis

Download link

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB04660

Drug Groups

experimental

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]

Affected Organisms

Humans and other mammals

References

• 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]

TRC

G598700

sn-Glycero-3-phosphocholine (Choline Alfoscerate) is a phospholipid; precursor in choline biosynthesis. sn-Glycero-3-phosphocholine is an intermediate in catabolic pathway of phosphatidylcholine. sn-Glycero-3-phosphocholine is used as an Nootropic.

ChEBI

CHEBI:16870

A member of the class of phosphocholines that is the choline ester of sn-glycero-3-phosphate. It is one of the major osmolyte in the renal medullary cells.

Molecule Details

References

PubChem Literature

From Data Sources

• Olson, D., et al.: Science, 270, 1967 (1945)

• Schmidt, G., et al.: J. Biol. Chem., 161, 523 (1945)

• Frattola, L., et al.: Curr. Ther. Res., 49, 683 (1945)

References

Bioactivity

PubChem BioAssay

Bioactivity

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