Common NameSn-glycerol 3-phosphocholine
DescriptionGlycerophosphorylcholine (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
Molecular FormulaC8H20NO6P
Average Mass257.22300
Monoisotopic Mass257.10282
IUPAC Name(2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2s)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry Number28319-77-9
SMILESC[N+](C)(C)CCOP(=O)([O-])OC[C@H](O)CO
InChI IdentifierInChI=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
InChI KeySUHOQUVVVLNYQR-MRVPVSSYSA-N
CHEBI IDCHEBI:16870
HMDB IDHMDB0000086
Pathways
NameSMPDB/PathBank
Retinol Metabolism
Vitamin A Deficiency
StateNot Available
Water Solubility8.96e+00 g/l
logP-2.56
logS-1.54
pKa (Strongest Acidic)1.86
pKa (Strongest Basic)-2.97
Hydrogen Acceptor Count4
Hydrogen Donor Count2
Polar Surface Area99.05 Ų
Rotatable Bond Count8
Physiological Charge0
Formal Charge0
Refractivity68.68 m³·mol⁻¹
Polarizability24.42

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