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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:30 UTC
HMDB IDHMDB0001565
Secondary Accession Numbers
  • HMDB0000284
  • HMDB00284
  • HMDB01565
Metabolite Identification
Common NamePhosphorylcholine
DescriptionPhosphorylcholine, also known as choline phosphate or CHOP, belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. The phosphate of choline, and the parent compound of the phosphorylcholine family. Phosphorylcholine exists in all living species, ranging from bacteria to humans. Within humans, phosphorylcholine participates in a number of enzymatic reactions. In particular, phosphorylcholine can be converted into choline through its interaction with the enzyme phosphoethanolamine/phosphocholine phosphatase. In addition, phosphorylcholine can be converted into CDP-choline; which is mediated by the enzyme choline-phosphate cytidylyltransferase a. In humans, phosphorylcholine is involved in phospholipid biosynthesis. Outside of the human body, phosphorylcholine has been detected, but not quantified in several different foods, such as barley, pak choy, black radish, saskatoon berries, and acorns.
Structure
Data?1582752210
Synonyms
ValueSource
Choline phosphateChEBI
CHOPChEBI
N-Trimethyl-2-aminoethylphosphonateChEBI
O-PhosphocholineChEBI
Phosphoryl-cholineChEBI
Trimethyl(2-(phosphonooxy)ethyl)ammoniumChEBI
PhosphocholineKegg
Choline phosphoric acidGenerator
N-Trimethyl-2-aminoethylphosphonic acidGenerator
Chloride, phosphorylcholineHMDB
Phosphate, cholineHMDB
Phosphorylcholine chlorideHMDB
Phosphate chloride, cholineHMDB
Chloride, choline phosphateHMDB
Choline chloride dihydrogen phosphateHMDB
Choline phosphate chlorideHMDB
Chemical FormulaC5H15NO4P
Average Molecular Weight184.1507
Monoisotopic Molecular Weight184.073869485
IUPAC Name[2-(trimethylazaniumyl)ethoxy]phosphonic acid
Traditional NameChoP
CAS Registry Number3616-04-4
SMILES
C[N+](C)(C)CCOP(O)(O)=O
InChI Identifier
InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1
InChI KeyYHHSONZFOIEMCP-UHFFFAOYSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentPhosphocholines
Alternative Parents
Substituents
  • Phosphocholine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Tetraalkylammonium salt
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot 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]+Astarita_pos135.330932474
[M+H]+MetCCS_test_pos135.930932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.36 g/LALOGPS
logP-2.4ALOGPS
logP-4.8ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.15ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.07 m³·mol⁻¹ChemAxon
Polarizability17.23 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
DarkChem[M+H]+139.17531661259
DarkChem[M-H]-134.38131661259
AllCCS[M+H]+138.83732859911
AllCCS[M-H]-146.58532859911
DeepCCS[M+H]+127.03130932474
DeepCCS[M-H]-123.32730932474
DeepCCS[M-2H]-160.73830932474
DeepCCS[M+Na]+136.25830932474
AllCCS[M+H]+138.832859911
AllCCS[M+H-H2O]+135.332859911
AllCCS[M+NH4]+142.132859911
AllCCS[M+Na]+143.132859911
AllCCS[M-H]-146.632859911
AllCCS[M+Na-2H]-148.532859911
AllCCS[M+HCOO]-150.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhosphorylcholineC[N+](C)(C)CCOP(O)(O)=O2126.8Standard polar33892256
PhosphorylcholineC[N+](C)(C)CCOP(O)(O)=O1181.9Standard non polar33892256
PhosphorylcholineC[N+](C)(C)CCOP(O)(O)=O1473.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phosphorylcholine,1TMS,isomer #1C[N+](C)(C)CCOP(=O)(O)O[Si](C)(C)C1441.6Semi standard non polar33892256
Phosphorylcholine,1TMS,isomer #1C[N+](C)(C)CCOP(=O)(O)O[Si](C)(C)C1374.9Standard non polar33892256
Phosphorylcholine,1TMS,isomer #1C[N+](C)(C)CCOP(=O)(O)O[Si](C)(C)C1792.0Standard polar33892256
Phosphorylcholine,2TMS,isomer #1C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1466.2Semi standard non polar33892256
Phosphorylcholine,2TMS,isomer #1C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1490.9Standard non polar33892256
Phosphorylcholine,2TMS,isomer #1C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1537.0Standard polar33892256
Phosphorylcholine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(O)OCC[N+](C)(C)C1667.5Semi standard non polar33892256
Phosphorylcholine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(O)OCC[N+](C)(C)C1612.6Standard non polar33892256
Phosphorylcholine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(O)OCC[N+](C)(C)C1887.7Standard polar33892256
Phosphorylcholine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C1918.9Semi standard non polar33892256
Phosphorylcholine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C1919.0Standard non polar33892256
Phosphorylcholine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C1731.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phosphorylcholine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-cb21d52ab18bca51e7772016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphorylcholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-0900000000-3d961174f1a27a76e3512012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000i-9300000000-fff62078da4bf8f847532012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-007a-9000000000-275c66ca16bdb9344ee22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-001i-0900000000-1dbd5123486fc544909b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-001r-4900000000-a77ea15e15088c9209fe2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-002r-9600000000-55422f402ca1581e81112012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-0072-9100000000-80e4e45c1a0a5ef016ce2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-006t-9000000000-347eed4168ee481957532012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0040-6900000000-8bbb64f5a93a59787a0d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-001i-9700000000-1e35f21857e363fec75a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QTOF , negative-QTOFsplash10-001i-9700000000-1e35f21857e363fec75a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ , positive-QTOFsplash10-001i-0900000000-1dbd5123486fc544909b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ , positive-QTOFsplash10-001r-4900000000-2fd51d187f11ab05dd9f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ , positive-QTOFsplash10-002r-9600000000-57b8ad3f9f3c91e92bdf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ , positive-QTOFsplash10-0072-9100000000-80e4e45c1a0a5ef016ce2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ , positive-QTOFsplash10-006t-9000000000-347eed4168ee481957532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QTOF , positive-QTOFsplash10-0040-6900000000-8bbb64f5a93a59787a0d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine 35V, Positive-QTOFsplash10-001i-3900000000-d64b56779c67fb13738d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine 20V, Positive-QTOFsplash10-00ds-9200000000-e65557cea0495452a5be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine 35V, Positive-QTOFsplash10-001i-4900000000-4d34ff6b3e7ac6a8a67a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine 40V, Positive-QTOFsplash10-000t-9000000000-a00e7417eed2c9707fe52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphorylcholine 10V, Positive-QTOFsplash10-001i-2900000000-08400ca570d2f786b4db2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphorylcholine 10V, Positive-QTOFsplash10-001r-9500000000-7b0806b933e054fe2fc12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphorylcholine 20V, Positive-QTOFsplash10-001r-9200000000-8134826bf94ee033006d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphorylcholine 40V, Positive-QTOFsplash10-000i-9000000000-b75c9abd7c4ad9a577762017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Placenta
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.2 +/- 1.0 uMAdult (>18 years old)Female
Normal
details
Breast MilkDetected and Quantified355 +/- 171 uMAdult (>18 years old)Female
Normal
details
Breast MilkDetected and Quantified570 +/- 136 uMAdult (>18 years old)FemaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.42 +/- 0.71 uMAdult (>18 years old)Not SpecifiedNormal 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 and Quantified5.21 +/- 2.21 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified5.24 +/- 1.97 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified5.42 +/- 3.54 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified2.21 +/- 2.22 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified3.46 +/- 1.59 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified13.11 +/- 9.45 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified4.44 +/- 2.30 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.1 (0.7-3.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Lung cancer
details
Cerebrospinal Fluid (CSF)Detected and Quantified2.32 +/- 0.38 uMAdult (>18 years old)Not SpecifiedVascular dementia details
Cerebrospinal Fluid (CSF)Detected and Quantified2.16 +/- 0.84 uMElderly (>65 years old)Not SpecifiedAlzheimer's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer
details
Associated Disorders and Diseases
Disease References
Lung Cancer
  1. Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
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 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB03945
Phenol Explorer Compound IDNot Available
FooDB IDFDB031111
KNApSAcK IDC00007299
Chemspider ID989
KEGG Compound IDC00588
BioCyc IDPHOSPHORYL-CHOLINE
BiGG ID48308
Wikipedia LinkPhosphorylcholine
METLIN ID6326
PubChem Compound1014
PDB IDNot Available
ChEBI ID18132
Food Biomarker OntologyNot Available
VMH IDCHOLP
MarkerDB IDMDB00000338
Good Scents IDNot Available
References
Synthesis ReferenceVijeeta, T.; Reddy, J. R. C.; Rao, B. V. S. K.; Karuna, M. S. L.; Prasad, R. B. N. Phospholipase-mediated preparation of 1-ricinoleoyl-2-acyl-sn- glycero-3-phosphocholine from soya and egg phosphatidylcholine. Biotechnology Letters (2004), 26(13), 1077-10
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  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 ]
  2. 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 ]
  3. 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 ]
  4. Katz-Brull R, Margalit R, Degani H: Differential routing of choline in implanted breast cancer and normal organs. Magn Reson Med. 2001 Jul;46(1):31-8. [PubMed:11443708 ]
  5. Stoll AL, Renshaw PF, De Micheli E, Wurtman R, Pillay SS, Cohen BM: Choline ingestion increases the resonance of choline-containing compounds in human brain: an in vivo proton magnetic resonance study. Biol Psychiatry. 1995 Feb 1;37(3):170-4. [PubMed:7727625 ]
  6. Nordenstam G, Andersson B, Briles D, Brooks JW Jr, Oden A, Svanborg A, Eden CS: High anti-phosphorylcholine antibody levels and mortality associated with pneumonia. Scand J Infect Dis. 1990;22(2):187-95. [PubMed:2356441 ]
  7. Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5. [PubMed:25935 ]
  8. Toth M, Gimes G: Phosphocholine transferase is more efficient than diacylglycerol kinase as possible attenuator of diacylglycerol signals in primordial human placenta. Acta Physiol Hung. 1993;81(4):341-54. [PubMed:8067249 ]
  9. Kanekura T, Nagata Y, Miyoshi H, Ishihara K, Nakabayashi N, Kanzaki T: Beneficial effects of synthetic phospholipid polymer, poly(2-methacryloyloxyethyl phosphorylcholine-co-n-butyl methacrylate), on stratum corneum function. Clin Exp Dermatol. 2002 May;27(3):230-4. [PubMed:12072015 ]
  10. Ueda H, Watanabe J, Konno T, Takai M, Saito A, Ishihara K: Asymmetrically functional surface properties on biocompatible phospholipid polymer membrane for bioartificial kidney. J Biomed Mater Res A. 2006 Apr;77(1):19-27. [PubMed:16345080 ]
  11. Kanfer JN, Pettegrew JW, Moossy J, McCartney DG: Alterations of selected enzymes of phospholipid metabolism in Alzheimer's disease brain tissue as compared to non-Alzheimer's demented controls. Neurochem Res. 1993 Mar;18(3):331-4. [PubMed:8386814 ]
  12. Hartwich J, Dembinska-Kiec A, Gruca A, Motyka M, Partyka L, Skrzeczynska J, Bzowska M, Pryjma J, Huber J, Leitinger N, Schmitz G: Regulation of platelet adhesion by oxidized lipoproteins and oxidized phospholipids. Platelets. 2002 May;13(3):141-51. [PubMed:12180496 ]
  13. Nakabayashi N, Iwasaki Y: Copolymers of 2-methacryloyloxyethyl phosphorylcholine (MPC) as biomaterials. Biomed Mater Eng. 2004;14(4):345-54. [PubMed:15472384 ]
  14. Jansen SM, Groener JE, Bax W, Suter A, Saftig P, Somerharju P, Poorthuis BJ: Biosynthesis of phosphatidylcholine from a phosphocholine precursor pool derived from the late endosomal/lysosomal degradation of sphingomyelin. J Biol Chem. 2001 Jun 1;276(22):18722-7. Epub 2001 Mar 16. [PubMed:11376003 ]
  15. Iwasaki Y, Yamasaki A, Ishihara K: Platelet compatible blood filtration fabrics using a phosphorylcholine polymer having high surface mobility. Biomaterials. 2003 Sep;24(20):3599-604. [PubMed:12809789 ]
  16. Tomassen SF, Fekkes D, de Jonge HR, Tilly BC: Osmotic swelling-provoked release of organic osmolytes in human intestinal epithelial cells. Am J Physiol Cell Physiol. 2004 Jun;286(6):C1417-22. Epub 2004 Feb 11. [PubMed:14960416 ]
  17. Dagnelie PC, Bell JD, Cox IJ, Menon DK, Sargentoni J, Coutts GA, Williams SC: Effects of fish oil on phospholipid metabolism in human and rat liver studied by 31P NMR spectroscopy in vivo and in vitro. NMR Biomed. 1993 Mar-Apr;6(2):157-62. [PubMed:8499247 ]
  18. Bell JD, Cox IJ, Sargentoni J, Peden CJ, Menon DK, Foster CS, Watanapa P, Iles RA, Urenjak J: A 31P and 1H-NMR investigation in vitro of normal and abnormal human liver. Biochim Biophys Acta. 1993 Nov 25;1225(1):71-7. [PubMed:8241291 ]
  19. Zhu X, Song J, Mar MH, Edwards LJ, Zeisel SH: Phosphatidylethanolamine N-methyltransferase (PEMT) knockout mice have hepatic steatosis and abnormal hepatic choline metabolite concentrations despite ingesting a recommended dietary intake of choline. Biochem J. 2003 Mar 15;370(Pt 3):987-93. [PubMed:12466019 ]
  20. Planchart S, Botto C, Alarcon de Noya B, Bonifacino R, Vivas L, Spencer L, Vivas S: Evaluation of the double diffusion, enzyme immunoassay and immunoblotting techniques, for the diagnosis of human hydatid disease in tropical areas. Rev Inst Med Trop Sao Paulo. 1994 May-Jun;36(3):205-10. [PubMed:7855483 ]
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Only showing the first 10 proteins. There are 14 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Controls phosphatidylcholine synthesis.
Gene Name:
PCYT1B
Uniprot ID:
Q9Y5K3
Molecular weight:
40228.99
Reactions
Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + Citicolinedetails
Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + CMP-N-trimethyl-2-aminoethylphosphonatedetails
General function:
Involved in catalytic activity
Specific function:
Controls phosphatidylcholine synthesis.
Gene Name:
PCYT1A
Uniprot ID:
P49585
Molecular weight:
41730.67
Reactions
Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + Citicolinedetails
Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + CMP-N-trimethyl-2-aminoethylphosphonatedetails
General function:
Involved in hydrolase activity
Specific function:
Converts sphingomyelin to ceramide. Also has phospholipase C activities toward 1,2-diacylglycerolphosphocholine and 1,2-diacylglycerolphosphoglycerol. Isoform 2 and isoform 3 have lost catalytic activity.
Gene Name:
SMPD1
Uniprot ID:
P17405
Molecular weight:
69935.53
Reactions
Sphingomyelin + Water → N-acylsphingosine + Phosphorylcholinedetails
Sphingomyelin + Water → N-Acylsphingosine + Phosphorylcholinedetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Has a key role in phospholipid biosynthesis. Catalyzes the first step in phosphatidylethanolamine biosynthesis. Phosphorylates ethanolamine, and can also act on choline (in vitro). Has higher activity with ethanolamine. May not significantly contribute to in vivo phosphatidylcholine biosynthesis.
Gene Name:
CHKB
Uniprot ID:
Q9Y259
Molecular weight:
45270.99
Reactions
Adenosine triphosphate + Choline → ADP + Phosphorylcholinedetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Has a key role in phospholipid biosynthesis and may contribute to tumor cell growth. Catalyzes the first step in phosphatidylcholine biosynthesis. Contributes to phosphatidylethanolamine biosynthesis. Phosphorylates choline and ethanolamine. Has higher activity with choline.
Gene Name:
CHKA
Uniprot ID:
P35790
Molecular weight:
52248.53
Reactions
Adenosine triphosphate + Choline → ADP + Phosphorylcholinedetails
General function:
Involved in catalytic activity
Specific function:
Converts sphingomyelin to ceramide. Also has phospholipase C activity toward palmitoyl lyso-phosphocholine. Does not appear to have nucleotide pyrophosphatase activity.
Gene Name:
ENPP7
Uniprot ID:
Q6UWV6
Molecular weight:
51493.415
Reactions
Sphingomyelin + Water → N-acylsphingosine + Phosphorylcholinedetails
Sphingomyelin + Water → N-Acylsphingosine + Phosphorylcholinedetails
General function:
Involved in metal ion binding
Specific function:
Converts sphingomyelin to ceramide. Hydrolyze 1-acyl-2-lyso-sn-glycero-3-phosphocholine (lyso-PC) and 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholine (lyso-platelet-activating factor). The physiological substrate seems to be Lyso-PAF.
Gene Name:
SMPD2
Uniprot ID:
O60906
Molecular weight:
47645.29
Reactions
Sphingomyelin + Water → N-acylsphingosine + Phosphorylcholinedetails
Sphingomyelin + Water → N-Acylsphingosine + Phosphorylcholinedetails
General function:
Involved in choline binding
Specific function:
Displays several functions associated with host defense:it promotes agglutination, bacterial capsular swelling, phagocytosis and complement fixation through its calcium-dependent binding to phosphorylcholine. Can interact with DNA and histones and may scavenge nuclear material released from damaged circulating cells
Gene Name:
CRP
Uniprot ID:
P02741
Molecular weight:
25038.4
General function:
Involved in phosphatase activity
Specific function:
Phosphatase that has a high activity toward phosphoethanolamine (PEA) and phosphocholine (PCho). Involved in the generation of inorganic phosphate for bone mineralization.
Gene Name:
PHOSPHO1
Uniprot ID:
Q8TCT1
Molecular weight:
32350.505
Reactions
Phosphorylcholine + Water → Choline + Phosphatedetails
General function:
Involved in metal ion binding
Specific function:
Catalyzes the hydrolysis of sphingomyelin to form ceramide and phosphocholine. Ceramide mediates numerous cellular functions, such as apoptosis and growth arrest, and is capable of regulating these 2 cellular events independently. Also hydrolyzes sphingosylphosphocholine. Regulates the cell cycle by acting as a growth suppressor in confluent cells. Probably acts as a regulator of postnatal development and participates in bone and dentin mineralization.
Gene Name:
SMPD3
Uniprot ID:
Q9NY59
Molecular weight:
71080.1
Reactions
Sphingomyelin + Water → N-acylsphingosine + Phosphorylcholinedetails
Sphingomyelin + Water → N-Acylsphingosine + Phosphorylcholinedetails

Only showing the first 10 proteins. There are 14 proteins in total.