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

• ChemBase编号: 4220
• 分子式: C8H20NO6P
• 平均质量: 257.221261
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2-{[(S)-((2R)-2,3-dihydroxypropyl phosphonato)]oxy}ethyl)trimethylazanium; (2-{[(2R)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC传统名: (2-{[(S)-((2R)-2,3-dihydroxypropyl phosphonato)]oxy}ethyl)trimethylazanium; α-gpc
• 别名: 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

登记号

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

理论计算性质

JChem

• Acid pKa: 1.8553451
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): -3.7048078
• LogD (pH = 7.4): -3.7047117
• Log P: -5.7283115
• 摩尔折射率: 68.6823 cm^3
• 极化性: 23.408195 Å^3
• 极化表面积: 99.05 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.46
• LOG S: -1.86
• 溶解度: 4.04e+00 g/l

分子性质

理化性质

• 溶解度: Methanol
• 外观: White Solid
• 熔点: 130-134°C

安全信息

• 保存条件: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

详细说明

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.

参考文献

• 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)