ChemFOnt: Showing chemical card for Glycerophosphocholine (CFc000000059)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:21 UTC

Chemfont ID

CFc000000059

Molecule Identification

Common Name

Glycerophosphocholine

Definition

Glycerophosphorylcholine (GPC) is a choline derivative and one of the two major forms of choline storage (along with phosphocholine) in the cytosol. Glycerophosphorylcholine is also one of the four major organic osmolytes in renal medullary cells, changing their intracellular osmolyte concentration in parallel with extracellular tonicity during cellular osmoadaptation. As an osmolyte, Glycerophosphorylcholine counteracts the effects of urea on enzymes and other macromolecules. Kidneys (especially medullar cells), which are exposed under normal physiological conditions to widely fluctuating extracellular solute concentrations, respond to hypertonic stress by accumulating the organic osmolytes glycerophosphorylcholine (GPC), betaine, myo-inositol, sorbitol and free amino acids. Increased intracellular contents of these osmolytes are achieved by a combination of increased uptake (myo-inositol and betaine) and synthesis (sorbitol, GPC), decreased degradation (GPC) and reduced osmolyte release. GPC is formed in the breakdown of phosphatidylcholine (PtC). This pathway is active in many body tissues, including mammary tissue.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Choline alfosceric acid	Generator
Glycerophosphate, choline	MeSH
Alphoscerate, choline	MeSH
Choline glycerophosphate	MeSH
Glycerol 3 phosphocholine	MeSH
3-Phosphocholine, glycerol	MeSH
Glycerophosphorylcholine	MeSH
L alpha Glycerylphosphorylcholine	MeSH
Glycerol 3-phosphocholine	MeSH
Choline alphoscerate	MeSH
Alfoscerate, choline	MeSH
L-alpha-Glycerylphosphorylcholine	MeSH

Chemical Formula

C₈H₂₀NO₆P

Average Molecular Weight

257.2213

Monoisotopic Molecular Weight

257.102823889

IUPAC Name

{2-[(2,3-dihydroxypropyl phosphono)oxy]ethyl}trimethylazanium

Traditional Name

{2-[(2,3-dihydroxypropyl phosphono)oxy]ethyl}trimethylazanium

CAS Registry Number

28319-77-9

SMILES

C[N+](C)(C)CCOP([O-])(=O)OCC(O)CO

InChI Identifier

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

InChI Key

SUHOQUVVVLNYQR-UHFFFAOYSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Glycerophosphocholines

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 Framework

Aliphatic acyclic compounds

External Descriptors

a small molecule (L-1-GLYCERO-PHOSPHORYLCHOLINE )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Breast milk (PMID: 8839502)
Blood (PMID: 16043031)
Semen (PMID: 2827914)
Cerebrospinal Fluid (CSF) (PMID: 15465626)
Saliva (PMID: 20300169)

Organ

Excreta

Biofluid or Excreta

Feces (PMID: 27065191)
Urine (PMID: 32966057)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0000086)

Endogenous

Endogenous (HMDB: HMDB0000086)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Retinol Metabolism (PathBank: SMP0087353)
Choline Metabolism (PathBank: SMP0002393)
Lysolipid Incorporation into ER (PathBank: SMP0002425)
Lysolipid Incorporation into ER PC(10:0/10:0) (PathBank: SMP0002512)
Lysolipid Incorporation into ER PC(14:0/14:0) (PathBank: SMP0002513)
Lysolipid Incorporation into ER PC(16:0/16:0) (PathBank: SMP0002514)
Lysolipid Incorporation into ER PC(16:1(9Z)/16:1(9Z)) (PathBank: SMP0002515)
Lysolipid Incorporation into ER PC(16:1(11Z)/16:1(11Z)) (PathBank: SMP0002516)
Lysolipid Incorporation into ER PC(18:0/18:0) (PathBank: SMP0002517)
Lysolipid Incorporation into ER PC(18:1(9Z)/18:1(9Z)) (PathBank: SMP0002518)
Lysolipid Incorporation into ER PC(18:2(9Z,11Z)/18:2(9Z,11Z)) (PathBank: SMP0002519)
Lysolipid Incorporation into ER PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0002520)

Disease pathway

Vitamin A Deficiency (PathBank: SMP0120500)

Role

Industrial application

Pharmaceutical industry

Biomarker

Alzheimer's Disease (MarkerDB: MDB00000045)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.96 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-5.7	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.05 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	68.68 m³·mol⁻¹	ChemAxon
Polarizability	24.82 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021802

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alpha-GPC

METLIN ID

Not Available

PubChem Compound

11234

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Evans, Christopher Thomas; McCague, Raymond; Tyrrell, Nicholas David. Preparation of phospholipid-intermediate glycerophosphocholine by a crystallization process. PCT Int. Appl. (1993), 8 pp.

Showing chemical card for Glycerophosphocholine (CFc000000059)

MOL for CFc000000059 (Glycerophosphocholine)

3D MOL for CFc000000059 (Glycerophosphocholine)

3D SDF for CFc000000059 (Glycerophosphocholine)

3D-SDF for CFc000000059 (Glycerophosphocholine)

PDB for CFc000000059 (Glycerophosphocholine)

3D PDB for CFc000000059 (Glycerophosphocholine)

SMILES for CFc000000059 (Glycerophosphocholine)

INCHI for CFc000000059 (Glycerophosphocholine)

Structure for CFc000000059 (Glycerophosphocholine)

3D Structure for CFc000000059 (Glycerophosphocholine)