Human Metabolome Database Version 3.5

Showing metabocard for Phosphorylcholine (HMDB01565)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:32:15 -0600
HMDB ID HMDB01565
Secondary Accession Numbers
  • HMDB00284
Metabolite Identification
Common Name Phosphorylcholine
Description Phosphorylcholine 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 Link_out). 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Choline phosphate
  2. N-Trimethyl-2-aminoethylphosphonate
  3. O-Phosphocholine
  4. Phosphocholine
  5. Phosphoryl-choline
Chemical Formula C5H15NO4P
Average Molecular Weight 184.1507
Monoisotopic Molecular Weight 184.073869485
IUPAC Name [2-(trimethylazaniumyl)ethoxy]phosphonic acid
Traditional IUPAC Name 2-(trimethylaminio)ethoxyphosphonic acid
CAS Registry Number 3616-04-4
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 Key YHHSONZFOIEMCP-UHFFFAOYSA-O
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Alcohols and Polyols
Sub Class Cholines
Other Descriptors
  • Cholines
  • phosphocholines(ChEBI)
Substituents
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoethanolamine
  • Phosphoric Acid Ester
  • Quaternary Ammonium Salt
Direct Parent Phosphocholines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminophosphonate metabolism
  • Component of Glycerophospholipid metabolism
  • Component of Glycine, serine and threonine metabolism
  • Component of Glycosphingolipid metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 4.36 g/L ALOGPS
LogP -2.43 ALOGPS
LogP -4.8 ChemAxon
LogS -1.70 ALOGPS
pKa (strongest acidic) 1.15 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.76 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 53.07 ChemAxon
Polarizability 17.23 ChemAxon
Formal Charge 1 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Placenta
  • Kidney
  • Liver
  • Epidermis
  • Brain
  • Platelet
  • Stratum Corneum
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
2.2 +/- 1.0 uM Adult (>18 years old) Female Comment Normal
Breast Milk Detected and Quantified
570 +/- 136 uM Adult (>18 years old) Female Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
1.42 +/- 0.71 uM Adult (>18 years old) Not Specified Normal
Urine Detected and Quantified
1.1 (0.7-3.0) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 2.32 +/- 0.38 uM Adult (>18 years old) Not Specified Vascular dementia
Cerebrospinal Fluid (CSF) Detected and Quantified 2.16 +/- 0.84 uM Elderly (>65 years old) Not Specified Alzheimer's disease
Associated Disorders and Diseases
Disease References
Multi-infarct dementia
  • 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 Link_out
      Alzheimer's disease
      • 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 Link_out
          Associated OMIM IDs
          DrugBank ID Not Available
          DrugBank Metabolite ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB022692
          KNApSAcK ID Not Available
          Chemspider ID 989 Link_out
          KEGG Compound ID C00588 Link_out
          BioCyc ID PHOSPHORYL-CHOLINE Link_out
          BiGG ID 48308 Link_out
          Wikipedia Link Phosphorylcholine Link_out
          NuGOwiki Link HMDB01565 Link_out
          Metagene Link HMDB01565 Link_out
          METLIN ID 6326 Link_out
          PubChem Compound 1014 Link_out
          PDB ID PC Link_out
          ChEBI ID 18132 Link_out
          References
          Synthesis Reference Vijeeta, 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. 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 Link_out
          2. 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 Link_out
          3. Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5. Pubmed: 25935 Link_out
          4. 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 Link_out
          5. 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 Link_out
          6. 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 Link_out
          7. 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 Link_out
          8. 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 Link_out
          9. 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 Link_out
          10. Nakabayashi N, Iwasaki Y: Copolymers of 2-methacryloyloxyethyl phosphorylcholine (MPC) as biomaterials. Biomed Mater Eng. 2004;14(4):345-54. Pubmed: 15472384 Link_out
          11. 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 Link_out
          12. 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 Link_out
          13. 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 Link_out
          14. 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 Link_out
          15. 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 Link_out
          16. 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 Link_out
          17. 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 Link_out
          18. 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 Link_out
          19. 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 Link_out
          20. 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 Link_out
          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 Link_out

          Enzymes
          Name: Choline-phosphate cytidylyltransferase B
          Reactions:
          Cytidine triphosphate + Phosphorylcholine unknown Pyrophosphate + Citicoline details
          Cytidine triphosphate + Phosphorylcholine unknown Pyrophosphate + CMP-N-trimethyl-2-aminoethylphosphonate details
          Gene Name: PCYT1B
          Uniprot ID: Q9Y5K3 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Choline-phosphate cytidylyltransferase A
          Reactions:
          Cytidine triphosphate + Phosphorylcholine unknown Pyrophosphate + Citicoline details
          Cytidine triphosphate + Phosphorylcholine unknown Pyrophosphate + CMP-N-trimethyl-2-aminoethylphosphonate details
          Gene Name: PCYT1A
          Uniprot ID: P49585 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Sphingomyelin phosphodiesterase
          Reactions:
          Sphingomyelin + Water unknown N-acylsphingosine + Phosphorylcholine details
          Sphingomyelin + Water unknown N-Acylsphingosine + Phosphorylcholine details
          Gene Name: SMPD1
          Uniprot ID: P17405 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Choline/ethanolamine kinase
          Reactions:
          Adenosine triphosphate + Choline unknown ADP + Phosphorylcholine details
          Gene Name: CHKB
          Uniprot ID: Q9Y259 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Choline kinase alpha
          Reactions:
          Adenosine triphosphate + Choline unknown ADP + Phosphorylcholine details
          Gene Name: CHKA
          Uniprot ID: P35790 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 7
          Reactions:
          Sphingomyelin + Water unknown N-acylsphingosine + Phosphorylcholine details
          Sphingomyelin + Water unknown N-Acylsphingosine + Phosphorylcholine details
          Gene Name: ENPP7
          Uniprot ID: Q6UWV6 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Sphingomyelin phosphodiesterase 2
          Reactions:
          Sphingomyelin + Water unknown N-acylsphingosine + Phosphorylcholine details
          Sphingomyelin + Water unknown N-Acylsphingosine + Phosphorylcholine details
          Gene Name: SMPD2
          Uniprot ID: O60906 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: C-reactive protein
          Reactions: Not Available
          Gene Name: CRP
          Uniprot ID: P02741 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Phosphoethanolamine/phosphocholine phosphatase
          Reactions:
          Phosphorylcholine + Water unknown Choline + Phosphoric acid details
          Gene Name: PHOSPHO1
          Uniprot ID: Q8TCT1 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Sphingomyelin phosphodiesterase 3
          Reactions:
          Sphingomyelin + Water unknown N-acylsphingosine + Phosphorylcholine details
          Sphingomyelin + Water unknown N-Acylsphingosine + Phosphorylcholine details
          Gene Name: SMPD3
          Uniprot ID: Q9NY59 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Sphingomyelin phosphodiesterase 4
          Reactions:
          Sphingomyelin + Water unknown N-acylsphingosine + Phosphorylcholine details
          Sphingomyelin + Water unknown N-Acylsphingosine + Phosphorylcholine details
          Gene Name: SMPD4
          Uniprot ID: Q9NXE4 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Epididymal sperm-binding protein 1
          Reactions: Not Available
          Gene Name: ELSPBP1
          Uniprot ID: Q96BH3 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 6
          Reactions:
          A lysophosphatidylcholine + Water unknown a monoacylglycerol + Phosphorylcholine details
          Glycerophosphocholine + Water unknown Glycerol + Phosphorylcholine details
          Gene Name: ENPP6
          Uniprot ID: Q6UWR7 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Manganese-dependent ADP-ribose/CDP-alcohol diphosphatase
          Reactions:
          Citicoline + Water unknown Cytidine monophosphate + Phosphorylcholine details
          Gene Name: ADPRM
          Uniprot ID: Q3LIE5 Link_out
          Protein Sequence: FASTA