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

• ChemBase ID: 4220
• Molecular Formular: C8H20NO6P
• Molecular Mass: 257.221261
• Monoisotopic Mass: 257.102824
• SMILES: C[N+](C)(C)CCOP(=O)([O-])OC[C@H](O)CO
• Canonical SMILES: OC[C@H](COP(=O)(OCC[N+](C)(C)C)[O-])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/t8-/m1/s1
• InChIKey: SUHOQUVVVLNYQR-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(S)-((2R)-2,3-dihydroxypropyl phosphonato)]oxy}ethyl)trimethylazanium; (2-{[(2R)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(S)-((2R)-2,3-dihydroxypropyl phosphonato)]oxy}ethyl)trimethylazanium; α-gpc
• Synonyms: glycero-3-phosphocholine; Choline Alfoscerate; SN-glycero-3-phosphocholine; L-alpha-Glycerophosphocholine; L-alpha-Glycerophosphorylcholine; L-alpha-Glycerylphosphorylcholine; 2-{[(2R)-2,3-dihydroxypropoxy](hydroxy)phosphoryloxy}-N,N,N-trimethylethanaminium; GPC; Glycerylphosphorylcholine; 2-[[[(2R)-2,3-Dihydroxypropoxy]hydroxyphosphinyl]oxy]-N,N,N-trimethylethanaminium Inner Salt; Brezal; Cereton; Cholicerin; Cholitiline; Delecit; Glycerylphosphocholine; Glycerylphosphorylcholine; L-α-GPC; L-α-Glycerophosphocholine; L-α-Glycerophosphorylcholine; L-α-Glycerylphosphorylcholine; O-(sn-glycero-3-Phosphoryl)choline; Sn-Glycerophosphocholine; sn-Glycero-3-phosphorylcholine; α-Glycerophosphorylcholine; α-Glycerylphosphorylcholine; sn-Glycero-3-phosphocholine

Database IDs

• CAS Number: 28319-77-9; 563-24-6
• PubChem SID: 160967652; 46508680
• PubChem CID: 657272; 439285

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8553451
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.7048078
• LogD (pH = 7.4): -3.7047117
• Log P: -5.7283115
• Molar Refractivity: 68.6823 cm^3
• Polarizability: 23.408195 Å^3
• Polar Surface Area: 99.05 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.46
• LOG S: -1.86
• Solubility (Water): 4.04e+00 g/l

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 130-134°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

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]

Toronto Research Chemicals - 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.

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
• Schmidt, G., et al.: J. Biol. Chem., 161, 523 (1945)
• Frattola, L., et al.: Curr. Ther. Res., 49, 683 (1945)
• Olson, D., et al.: Science, 270, 1967 (1945)