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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:32:15 UTC
HMDB IDHMDB01565
Secondary Accession Numbers
  • HMDB00284
Metabolite Identification
Common NamePhosphorylcholine
DescriptionPhosphorylcholine is a small haptenic molecule, is found in a wide variety of organisms. Human hepatic tumors undergo an elevation in the concentration of phosphorylcholine as the principal metabolic change is observed (PMID: 11076016 ). Phosphorylcholine is the precursor metabolite of choline in the glycine, serine and threonine metabolism pathways (KEGG, map00260) and in intermediate between choline and cytidine-diphosphate choline in the glycerophospholipid metabolism pathway (KEGG, map00564).
Structure
Thumb
Synonyms
  1. Choline phosphate
  2. N-Trimethyl-2-aminoethylphosphonate
  3. O-Phosphocholine
  4. Phosphocholine
  5. Phosphoryl-choline
Chemical FormulaC5H15NO4P
Average Molecular Weight184.1507
Monoisotopic Molecular Weight184.073869485
IUPAC Name[2-(trimethylazaniumyl)ethoxy]phosphonic acid
Traditional IUPAC Name2-(trimethylaminio)ethoxyphosphonic acid
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
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlcohols and Polyols
Sub ClassCholines
Other Descriptors
  • Cholines
  • phosphocholines(ChEBI)
Substituents
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoethanolamine
  • Phosphoric Acid Ester
  • Quaternary Ammonium Salt
Direct ParentPhosphocholines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminophosphonate metabolism
  • Component of Glycerophospholipid metabolism
  • Component of Glycine, serine and threonine metabolism
  • Component of Glycosphingolipid metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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 Area66.76ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.07ChemAxon
Polarizability17.23ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Placenta
  • Platelet
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.2 +/- 1.0 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
UrineDetected and Quantified1.1 (0.7-3.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
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. Pubmed: 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. Pubmed: 15465626
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022692
KNApSAcK IDNot Available
Chemspider ID989
KEGG Compound IDC00588
BioCyc IDPHOSPHORYL-CHOLINE
BiGG ID48308
Wikipedia LinkPhosphorylcholine
NuGOwiki LinkHMDB01565
Metagene LinkHMDB01565
METLIN ID6326
PubChem Compound1014
PDB IDPC
ChEBI ID18132
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
  21. Lochnit G, Dennis RD, Geyer R: Phosphorylcholine substituents in nematodes: structures, occurrence and biological implications. Biol Chem. 2000 Sep-Oct;381(9-10):839-47. Pubmed: 11076016

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 + Phosphoric aciddetails
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
General function:
Involved in metal ion binding
Specific function:
Catalyzes the hydrolysis of membrane sphingomyelin to form phosphorylcholine and ceramide.
Gene Name:
SMPD4
Uniprot ID:
Q9NXE4
Molecular weight:
86192.575
Reactions
Sphingomyelin + Water → N-acylsphingosine + Phosphorylcholinedetails
Sphingomyelin + Water → N-Acylsphingosine + Phosphorylcholinedetails
General function:
Involved in single fertilization
Specific function:
Binds to spermatozoa upon ejaculation and may play a role in sperm capacitation. Has phosphorylcholine-binding activity
Gene Name:
ELSPBP1
Uniprot ID:
Q96BH3
Molecular weight:
26106.1
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
A lysophosphatidylcholine + Water → a monoacylglycerol + Phosphorylcholinedetails
Glycerophosphocholine + Water → Glycerol + Phosphorylcholinedetails
General function:
Not Available
Specific function:
Hydrolyzes ADP-ribose, IDP-ribose, CDP-glycerol, CDP-choline and CDP-ethanolamine, but not other non-reducing ADP-sugars or CDP-glucose. May be involved in immune cell signaling as suggested by the second-messenger role of ADP-ribose, which activates TRPM2 as a mediator of oxidative/nitrosative stress (By similarity).
Gene Name:
ADPRM
Uniprot ID:
Q3LIE5
Molecular weight:
39529.105
Reactions
Citicoline + Water → Cytidine monophosphate + Phosphorylcholinedetails