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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-13 02:07:06 UTC
HMDB IDHMDB00086
Secondary Accession Numbers
  • HMDB00049
Metabolite Identification
Common NameGlycerophosphocholine
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
Thumb
Synonyms
ValueSource
2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium inner saltHMDB
a-GlycerophosphorylcholineHMDB
a-GlycerylphosphorylcholineHMDB
alpha-GlycerophosphorylcholineHMDB
alpha-GlycerylphosphorylcholineHMDB
Choline alfoscerateHMDB
Choline glycerophosphateHMDB
Glycerol 3-phosphocholineHMDB
Glycerol phosphorylcholineHMDB
Glycerol-3-phosphatidylcholineHMDB
GlycerophosphatidylcholineHMDB
GlycerophosphorylcholineHMDB
GPCHMDB
GPChoHMDB
Hydrogen glycerophosphate cholineHMDB
L-alpha-GlycerophosphocholineHMDB
L-alpha-GlycerophosphorylcholineHMDB
L-alpha-GlycerylphosphorylcholineHMDB
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner saltHMDB
sn-glycero-3-PhosphocholineHMDB
Chemical FormulaC8H20NO6P
Average Molecular Weight257.2213
Monoisotopic Molecular Weight257.102823889
IUPAC Name(2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
Traditional NameAlpha-GPC
CAS Registry Number28319-77-9
SMILES
C[N+](C)(C)CCOP([O-])(=O)OC[C@@H](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/t8-/m0/s1
InChI KeyInChIKey=SUHOQUVVVLNYQR-QMMMGPOBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentGlycerophosphocholines
Alternative Parents
Substituents
  • Glycero-3-phosphocholine
  • Phosphocholine
  • Dialkyl phosphate
  • Choline
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Saccharide
  • Quaternary ammonium salt
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Organic salt
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Glycerophospholipid metabolism
  • Component of Prostaglandin and leukotriene metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.96 mg/mLALOGPS
logP-2.6ALOGPS
logP-5.7ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.05 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity68.68 m3·mol-1ChemAxon
Polarizability24.42 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Semen
Tissue Location
  • Brain
  • Kidney
  • Most Tissues
  • Prostate
  • Spleen
Pathways
NameSMPDB LinkKEGG Link
Retinol MetabolismSMP00074map00830
Vitamin A DeficiencySMP00336Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified34.0 +/- 5.0 uMInfant (0-1 year old)Both
Normal
details
BloodDetected and Quantified40.0 +/- 4.0 uMNewborn (0-30 days old)Both
Normal
details
BloodDetected and Quantified29.0 +/- 5.0 uMInfant (0-1 year old)Both
Normal
details
BloodDetected and Quantified33.0 +/- 4.0 uMAdult (>18 years old)FemaleNormal details
Breast MilkDetected and Quantified471 +/- 161 uMAdult (>18 years old)Female
Normal
details
Breast MilkDetected and Quantified362 +/- 70 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified3.94 +/- 1.17 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified3.9 +/- 1.2 uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
SalivaDetected and Quantified1.05 +/- 0.248 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.38 +/- 0.531 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.84 +/- 0.652 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.98 +/- 1.45 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified2.53 +/- 4.35 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified9.82 +/- 6.76 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SemenDetected and Quantified2.5 +/- 1.6 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Kidney cancer
details
Cerebrospinal Fluid (CSF)Detected and Quantified4.03 +/- 1.52 uMElderly (>65 years old)Not SpecifiedVascular dementia details
Cerebrospinal Fluid (CSF)Detected and Quantified4.03 (2.51-5.55) uMAdult (>18 years old)BothVascular dementia details
Cerebrospinal Fluid (CSF)Detected and Quantified6.9 +/- 3.2 uMElderly (>65 years old)BothAlzheimer's disease details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothOral cancer details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleBreast cancer details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedPancreatic cancer details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedPeriodontal diseases details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Walter A, Korth U, Hilgert M, Hartmann J, Weichel O, Hilgert M, Fassbender K, Schmitt A, Klein J: Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Neurobiol Aging. 2004 Nov-Dec;25(10):1299-303. [15465626 ]
Multi-infarct dementia
  1. Walter A, Korth U, Hilgert M, Hartmann J, Weichel O, Hilgert M, Fassbender K, Schmitt A, Klein J: Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Neurobiol Aging. 2004 Nov-Dec;25(10):1299-303. [15465626 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021802
KNApSAcK IDNot Available
Chemspider ID64931
KEGG Compound IDC00670
BioCyc IDGLYCERYLPHOSPHORYLCHOLINE
BiGG ID35659
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00086
Metagene LinkHMDB00086
METLIN ID370
PubChem Compound71920
PDB IDNot Available
ChEBI ID16870
References
Synthesis ReferenceEvans, Christopher Thomas; McCague, Raymond; Tyrrell, Nicholas David. Preparation of phospholipid-intermediate glycerophosphocholine by a crystallization process. PCT Int. Appl. (1993), 8 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  2. Satlin A, Bodick N, Offen WW, Renshaw PF: Brain proton magnetic resonance spectroscopy (1H-MRS) in Alzheimer's disease: changes after treatment with xanomeline, an M1 selective cholinergic agonist. Am J Psychiatry. 1997 Oct;154(10):1459-61. [9326834 ]
  3. Walter A, Korth U, Hilgert M, Hartmann J, Weichel O, Hilgert M, Fassbender K, Schmitt A, Klein J: Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Neurobiol Aging. 2004 Nov-Dec;25(10):1299-303. [15465626 ]
  4. Theberge J, Al-Semaan Y, Jensen JE, Williamson PC, Neufeld RW, Menon RS, Schaefer B, Densmore M, Drost DJ: Comparative study of proton and phosphorus magnetic resonance spectroscopy in schizophrenia at 4 Tesla. Psychiatry Res. 2004 Nov 15;132(1):33-9. [15546701 ]
  5. Miller BL, Lin KM, Djenderedjian A, Tang C, Hill E, Fu P, Nuccio C, Jenden DJ: Changes in red blood cell choline and choline-bound lipids with oral lithium. Experientia. 1990 May 15;46(5):454-6. [2347393 ]
  6. Caetano SC, Fonseca M, Olvera RL, Nicoletti M, Hatch JP, Stanley JA, Hunter K, Lafer B, Pliszka SR, Soares JC: Proton spectroscopy study of the left dorsolateral prefrontal cortex in pediatric depressed patients. Neurosci Lett. 2005 Aug 26;384(3):321-6. [15936878 ]
  7. Nitsch R, Pittas A, Blusztajn JK, Slack BE, Growdon JH, Wurtman RJ: Alterations of phospholipid metabolites in postmortem brain from patients with Alzheimer's disease. Ann N Y Acad Sci. 1991;640:110-3. [1663712 ]
  8. Chap HJ, Moatti JP, Mieusset R, Nieto M, Laneelle G, Bennet PJ, Mansat A, Pontonnier F, Douste-Blazy L: Simple, rapid enzymatic determination of glycerophosphocholine in human seminal plasma. Clin Chem. 1988 Jan;34(1):106-9. [2827914 ]
  9. Blusztajn JK, Lopez Gonzalez-Coviella I, Logue M, Growdon JH, Wurtman RJ: Levels of phospholipid catabolic intermediates, glycerophosphocholine and glycerophosphoethanolamine, are elevated in brains of Alzheimer's disease but not of Down's syndrome patients. Brain Res. 1990 Dec 17;536(1-2):240-4. [2150771 ]
  10. Mandal PK, McClure RJ, Pettegrew JW: Interactions of Abeta(1-40) with glycerophosphocholine and intact erythrocyte membranes: fluorescence and circular dichroism studies. Neurochem Res. 2004 Dec;29(12):2273-9. [15672550 ]
  11. Pomfret EA, daCosta KA, Schurman LL, Zeisel SH: Measurement of choline and choline metabolite concentrations using high-pressure liquid chromatography and gas chromatography-mass spectrometry. Anal Biochem. 1989 Jul;180(1):85-90. [2817347 ]
  12. Nitsch RM, Blusztajn JK, Pittas AG, Slack BE, Growdon JH, Wurtman RJ: Evidence for a membrane defect in Alzheimer disease brain. Proc Natl Acad Sci U S A. 1992 Mar 1;89(5):1671-5. [1311847 ]
  13. Miller BL, Read S, Tang C, Jenden D: Differences in red blood cell choline and lipid-bound choline between patients with Alzheimer disease and control subjects. Neurobiol Aging. 1991 Jan-Feb;12(1):61-4. [2002884 ]
  14. Jensen JE, Drost DJ, Menon RS, Williamson PC: In vivo brain (31)P-MRS: measuring the phospholipid resonances at 4 Tesla from small voxels. NMR Biomed. 2002 Aug;15(5):338-47. [12203225 ]
  15. Zhang Q, Southall MD, Mezsick SM, Johnson C, Murphy RC, Konger RL, Travers JB: Epidermal peroxisome proliferator-activated receptor gamma as a target for ultraviolet B radiation. J Biol Chem. 2005 Jan 7;280(1):73-9. Epub 2004 Oct 29. [15516334 ]
  16. Fallbrook A, Turenne SD, Mamalias N, Kish SJ, Ross BM: Phosphatidylcholine and phosphatidylethanolamine metabolites may regulate brain phospholipid catabolism via inhibition of lysophospholipase activity. Brain Res. 1999 Jul 10;834(1-2):207-10. [10407117 ]
  17. Blank ML, Smith ZL, Fitzgerald V, Snyder F: The CoA-independent transacylase in PAF biosynthesis: tissue distribution and molecular species selectivity. Biochim Biophys Acta. 1995 Feb 9;1254(3):295-301. [7857969 ]

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:
LYPLA1
Uniprot ID:
O75608
Molecular weight:
24669.355
Reactions
1-Acyl-sn-glycero-3-phosphocholine + Water → Glycerophosphocholine + Fatty aciddetails
General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
Gene Name:
PLA2G15
Uniprot ID:
Q8NCC3
Molecular weight:
Not Available
Reactions
1-Acyl-sn-glycero-3-phosphocholine + Water → Glycerophosphocholine + Fatty aciddetails
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
Reactions
2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylatedetails
General function:
Involved in sugar binding
Specific function:
Has lysophospholipase activity.
Gene Name:
LGALS13
Uniprot ID:
Q9UHV8
Molecular weight:
16118.44
Reactions
2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylatedetails
General function:
Involved in hydrolase activity
Specific function:
May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:
LYPLA2
Uniprot ID:
O95372
Molecular weight:
24736.71
General function:
Involved in sugar binding
Specific function:
May have both lysophospholipase and carbohydrate-binding activities.
Gene Name:
CLC
Uniprot ID:
Q05315
Molecular weight:
16452.785
Reactions
2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylatedetails
General function:
Involved in asparaginase activity
Specific function:
Exhibits lysophospholipase, transacylase, PAF acetylhydrolase and asparaginase activities.
Gene Name:
ASPG
Uniprot ID:
Q86U10
Molecular weight:
60882.4
Reactions
2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylatedetails
General function:
Involved in hydrolase activity
Specific function:
Membrane-associated phospholipase. Exhibits a calcium-independent broad substrate specificity including phospholipase A2/lysophospholipase activity. Preferential hydrolysis at the sn-2 position of diacylphospholipids and diacyglycerol, whereas it shows no positional specificity toward triacylglycerol. Exhibits also esterase activity toward p-nitrophenyl. May act on the brush border membrane to facilitate the absorption of digested lipids (By similarity).
Gene Name:
PLB1
Uniprot ID:
Q6P1J6
Molecular weight:
161711.9
Reactions
2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylatedetails
1-Acyl-sn-glycero-3-phosphocholine + Water → Glycerophosphocholine + Fatty aciddetails
2-Acyl-sn-glycero-3-phosphocholine + Water → Glycerophosphocholine + Fatty aciddetails
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Has glycerophosphoinositol phosphodiesterase activity. Has little or no activity towards glycerophosphocholine. GDE1 activity can be modulated by G-protein signaling pathways (By similarity).
Gene Name:
GDE1
Uniprot ID:
Q9NZC3
Molecular weight:
37718.04
General function:
Involved in metabolic process
Specific function:
Calcium-independent phospholipase A2, which catalyzes the hydrolysis of the sn-2 position of glycerophospholipids, PtdSer and to a lower extent PtdCho. Cleaves membrane phospholipids.
Gene Name:
PNPLA8
Uniprot ID:
Q9NP80
Molecular weight:
88476.085
Reactions
2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylatedetails
General function:
Involved in metabolic process
Specific function:
Phospholipase B that deacylates intracellular phosphatidylcholine (PtdCho), generating glycerophosphocholine (GroPtdCho). This deacylation occurs at both sn-2 and sn-1 positions of PtdCho. Its specific chemical modification by certain organophosphorus (OP) compounds leads to distal axonopathy.
Gene Name:
PNPLA6
Uniprot ID:
Q8IY17
Molecular weight:
150952.43
Reactions
2-lysophosphatidylcholine + Water → Glycerophosphocholine + a carboxylatedetails
1-Acyl-sn-glycero-3-phosphocholine + Water → Glycerophosphocholine + Fatty aciddetails
2-Acyl-sn-glycero-3-phosphocholine + Water → Glycerophosphocholine + Fatty aciddetails
General function:
Involved in catalytic activity
Specific function:
Choline-specific glycerophosphodiester phosphodiesterase. The preferred substrate may be lysosphingomyelin (By similarity). Hydrolyzes lysophosphatidylcholine (LPC) to form monoacylglycerol and phosphorylcholine but not lysophosphatidic acid, showing it has a lysophospholipase C activity. Has a preference for LPC with short (12:0 and 14:0) or polyunsaturated (18:2 and 20:4) fatty acids. Also hydrolyzes glycerophosphorylcholine and sphingosylphosphorylcholine efficiently. Hydrolyzes the classical substrate for phospholipase C, p-nitrophenyl phosphorylcholine in vitro, while it does not hydrolyze the classical nucleotide phosphodiesterase substrate, p-nitrophenyl thymidine 5'-monophosphate. Does not hydrolyze diacyl phospholipids such as phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidylglycerol and phosphatidic acid.
Gene Name:
ENPP6
Uniprot ID:
Q6UWR7
Molecular weight:
50240.625
Reactions
Glycerophosphocholine + Water → Glycerol + Phosphorylcholinedetails
General function:
Not Available
Specific function:
May be involved in the negative regulation of skeletal muscle differentiation, independently of its glycerophosphocholine phosphodiesterase activity (By similarity).
Gene Name:
GPCPD1
Uniprot ID:
Q9NPB8
Molecular weight:
76034.185
Reactions
Glycerophosphocholine + Water → Choline + Glycerol 3-phosphatedetails
General function:
Not Available
Specific function:
Serine hydrolase, whose specific chemical modification by certain organophosphorus (OP) compounds leads to distal axonopathy (By similarity).
Gene Name:
PNPLA7
Uniprot ID:
Q6ZV29
Molecular weight:
Not Available
Reactions
1-Acyl-sn-glycero-3-phosphocholine + Water → Glycerophosphocholine + Fatty aciddetails
2-Acyl-sn-glycero-3-phosphocholine + Water → Glycerophosphocholine + Fatty aciddetails
General function:
Not Available
Specific function:
Enzyme catalyzing the degradation of lysoplasmalogen. Lysoplasmalogens are formed by the hydrolysis of the abundant membrane glycerophospholipids plasmalogens. May control the respective levels of plasmalogens and lysoplasmalogens in cells and modulate cell membrane properties.
Gene Name:
TMEM86B
Uniprot ID:
Q8N661
Molecular weight:
24351.695
Reactions
1-(1-alkenyl)-sn-glycero-3-phosphocholine + Water → an aldehyde + Glycerophosphocholinedetails