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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:48:59 UTC
HMDB IDHMDB0000086
Secondary Accession Numbers
  • HMDB0000049
  • HMDB00049
  • HMDB00086
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
Data?1582752111
Synonyms
ValueSource
(2R)-2,3-Dihydroxypropyl 2-(trimethylammonio)ethyl phosphateChEBI
Alfoscerate de cholineChEBI
Alfoscerato de colinaChEBI
alpha-GlycerophosphorylcholineChEBI
Choline alphoscerateChEBI
Choline glycerophosphateChEBI
Cholini alfoscerasChEBI
Cholini glycerophosphasChEBI
Glicerofosfato de colinaChEBI
Glycerol phosphorylcholineChEBI
Glycerol-3-phosphatidylcholineChEBI
Glycerol-3-phosphocholineChEBI
Glycerophosphate de cholineChEBI
GlycerophosphorylcholineChEBI
GPChoChEBI
L-alpha-GlycerophosphocholineChEBI
L-alpha-GlycerophosphorylcholineChEBI
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner saltChEBI
sn-3-GPCChEBI
sn-Glycero-3-phosphocholineChEBI
sn-Glycerol 3-phosphocholineChEBI
GliatilinKegg
(2R)-2,3-Dihydroxypropyl 2-(trimethylammonio)ethyl phosphoric acidGenerator
Alfosceric acid de cholineGenerator
a-GlycerophosphorylcholineGenerator
Α-glycerophosphorylcholineGenerator
Choline alphosceric acidGenerator
Choline glycerophosphoric acidGenerator
Glycerophosphoric acid de cholineGenerator
L-a-GlycerophosphocholineGenerator
L-Α-glycerophosphocholineGenerator
L-a-GlycerophosphorylcholineGenerator
L-Α-glycerophosphorylcholineGenerator
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphoric acid inner saltGenerator
Choline alfosceric acidHMDB
Glycerol 3 phosphocholineHMDB
GlycerylphosphorylcholineHMDB
Alphoscerate, cholineHMDB
L alpha GlycerylphosphorylcholineHMDB
3-Phosphocholine, glycerolHMDB
Glycerol 3-phosphocholineHMDB
L-alpha-GlycerylphosphorylcholineHMDB
Alfoscerate, cholineHMDB
Glycerophosphate, cholineHMDB
2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium inner saltHMDB
a-GlycerylphosphorylcholineHMDB
alpha-GlycerylphosphorylcholineHMDB
Choline alfoscerateHMDB
GlycerophosphatidylcholineHMDB
GPCHMDB
Hydrogen glycerophosphate cholineHMDB
CeretonHMDB
CholicerinHMDB
CholitilineHMDB
DelecitHMDB
Glycerol 3-phosphorylcholineHMDB
Glycerophosphoric acid choline esterHMDB
Glyceryl 3-phosphorylcholineHMDB
GlycerylphosphocholineHMDB
L-alpha-GPCHMDB
L-Α-GPCHMDB
L-Α-glycerylphosphorylcholineHMDB
O-(sn-Glycero-3-phosphoryl)-cholineHMDB
sn-Glycero-3-phosphorylcholineHMDB
Α-glycerylphosphorylcholineHMDB
GlycerophosphocholineChEBI
Chemical FormulaC8H20NO6P
Average Molecular Weight257.223
Monoisotopic Molecular Weight257.102824366
IUPAC Name(2-{[(2R)-2,3-dihydroxypropyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2,3-dihydroxypropyl phosphono]oxy}ethyl)trimethylazanium
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-/m1/s1
InChI KeySUHOQUVVVLNYQR-MRVPVSSYSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentGlycerophosphocholines
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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point142.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos155.53330932474
[M+H]+Not Available155.725http://allccs.zhulab.cn/database/detail?ID=AllCCS00000443
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.96 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity68.68 m³·mol⁻¹ChemAxon
Polarizability24.77 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+152.03230932474
DeepCCS[M-H]-149.81630932474
DeepCCS[M-2H]-183.27830932474
DeepCCS[M+Na]+157.94430932474
AllCCS[M+H]+155.632859911
AllCCS[M+H-H2O]+152.532859911
AllCCS[M+NH4]+158.432859911
AllCCS[M+Na]+159.232859911
AllCCS[M-H]-162.432859911
AllCCS[M+Na-2H]-163.532859911
AllCCS[M+HCOO]-164.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GlycerophosphocholineC[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO2743.9Standard polar33892256
GlycerophosphocholineC[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO1603.0Standard non polar33892256
GlycerophosphocholineC[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO1813.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glycerophosphocholine,1TMS,isomer #1C[N+](C)(C)CCOP(=O)([O-])OC[C@@H](CO)O[Si](C)(C)C1806.4Semi standard non polar33892256
Glycerophosphocholine,1TMS,isomer #2C[N+](C)(C)CCOP(=O)([O-])OC[C@H](O)CO[Si](C)(C)C1808.9Semi standard non polar33892256
Glycerophosphocholine,2TMS,isomer #1C[N+](C)(C)CCOP(=O)([O-])OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C1818.7Semi standard non polar33892256
Glycerophosphocholine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](CO)COP(=O)([O-])OCC[N+](C)(C)C2035.3Semi standard non polar33892256
Glycerophosphocholine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@@H](O)COP(=O)([O-])OCC[N+](C)(C)C2042.6Semi standard non polar33892256
Glycerophosphocholine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C2318.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glycerophosphocholine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-7910000000-79a0f6ec434740d094102017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerophosphocholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerophosphocholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerophosphocholine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerophosphocholine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerophosphocholine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerophosphocholine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerophosphocholine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerophosphocholine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycerophosphocholine 20V, Negative-QTOFsplash10-004i-9310000000-e2633e56c869520547102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycerophosphocholine 10V, Negative-QTOFsplash10-0a4i-1690000000-53ffc11b39ba8f89f8032021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycerophosphocholine 40V, Negative-QTOFsplash10-004i-9000000000-d4d2c5d7e0856e9486242021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycerophosphocholine 20V, Negative-QTOFsplash10-004i-9400000000-848201d8ac3bd454c67a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycerophosphocholine 40V, Positive-QTOFsplash10-01w1-9300000000-987e5431e2d611fa50322021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycerophosphocholine 10V, Negative-QTOFsplash10-0a4i-2490000000-efb55f1ddbed9f1a87542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycerophosphocholine 20V, Positive-QTOFsplash10-0udi-1900000000-df7b0a6ce3c788063f532021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycerophosphocholine 10V, Positive-QTOFsplash10-0zfr-0960000000-7df186ffc569be161b392021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerophosphocholine 10V, Positive-QTOFsplash10-052r-9140000000-3347b58fbc5fe0b0a2012019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerophosphocholine 20V, Positive-QTOFsplash10-0a7r-9210000000-60118aed826a14bb4cb12019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerophosphocholine 40V, Positive-QTOFsplash10-0a4r-9000000000-b6ac875e42841f04bcfc2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerophosphocholine 10V, Negative-QTOFsplash10-0a4i-0390000000-9adc870a20cd016e3aa22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerophosphocholine 20V, Negative-QTOFsplash10-0kor-2920000000-b31eb4ca99ba45d9f9312019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerophosphocholine 40V, Negative-QTOFsplash10-004i-9100000000-dec05a487d7ae73f1d272019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerophosphocholine 10V, Negative-QTOFsplash10-0a4i-0090000000-bd45c4f9a61bbdbbd2d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerophosphocholine 20V, Negative-QTOFsplash10-0a4i-3960000000-2d618fc6f1a9c434909c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerophosphocholine 40V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerophosphocholine 10V, Positive-QTOFsplash10-001i-0960000000-782cafcc84f2e1b585612021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerophosphocholine 20V, Positive-QTOFsplash10-001i-0900000000-5fbae562ef71fe1bd5522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerophosphocholine 40V, Positive-QTOFsplash10-0079-9800000000-00d2deed17b9ac0f57892021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Semen
  • Urine
Tissue Locations
  • Brain
  • Kidney
  • Placenta
  • Prostate
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>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 but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>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
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleMissing teeth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleProsthesis/Missing teeth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleBreast cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedPancreatic cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedPeriodontal diseases details
Associated Disorders and Diseases
Disease References
Kidney cancer
  1. Lin L, Huang Z, Gao Y, Chen Y, Hang W, Xing J, Yan X: LC-MS-based serum metabolic profiling for genitourinary cancer classification and cancer type-specific biomarker discovery. Proteomics. 2012 Aug;12(14):2238-46. doi: 10.1002/pmic.201200016. [PubMed:22685041 ]
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. [PubMed:15465626 ]
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. [PubMed:15465626 ]
Perillyl alcohol administration for cancer treatment
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Pancreatic cancer
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Periodontal disease
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Prosthesis/Missing teeth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Associated OMIM IDs
DrugBank IDDB04660
Phenol Explorer Compound IDNot Available
FooDB IDFDB030952
KNApSAcK IDNot Available
Chemspider ID571409
KEGG Compound IDC00670
BioCyc IDL-1-GLYCERO-PHOSPHORYLCHOLINE
BiGG IDNot Available
Wikipedia LinkAlpha-GPC
METLIN ID370
PubChem Compound657272
PDB IDNot Available
ChEBI ID16870
Food Biomarker OntologyNot Available
VMH IDG3PC
MarkerDB IDMDB00000045
Good Scents IDNot Available
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. doi: 10.1038/nature07762. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:7857969 ]
  18. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 15 proteins in total.

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

Only showing the first 10 proteins. There are 15 proteins in total.