| 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 |
|
| 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  ). 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- Choline phosphate
- N-Trimethyl-2-aminoethylphosphonate
- O-Phosphocholine
- Phosphocholine
- 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 |
|
| Biofunction |
- Component of Aminophosphonate metabolism
- Component of Glycerophospholipid metabolism
- Component of Glycine, serine and threonine metabolism
- Component of Glycosphingolipid metabolism
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| Application |
Not Available
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| Cellular locations |
- Cytoplasm (predicted from logP)
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| 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 |
|
| Spectra |
|---|
|
|
| Biological Properties |
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| Cellular Locations |
- Cytoplasm (predicted from logP)
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| Biofluid Locations |
- Blood
- Breast Milk
- Cerebrospinal Fluid (CSF)
- Urine
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| Tissue Location |
- Fibroblasts
- Intestine
- Placenta
- Kidney
- Liver
- Epidermis
- Brain
- Platelet
- Stratum Corneum
|
| Pathways |
Not Available
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| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
2.2 +/- 1.0 uM |
Adult (>18 years old) |
Female |
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 |
Normal
|
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| Abnormal Concentrations |
|---|
|
| 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
|
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| 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
|
| 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
|
|
| Associated OMIM IDs |
|
| External Links |
|---|
| 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 |
| KEGG Compound ID |
C00588 |
| BioCyc ID |
PHOSPHORYL-CHOLINE |
| BiGG ID |
48308 |
| Wikipedia Link |
Phosphorylcholine |
| NuGOwiki Link |
HMDB01565 |
| Metagene Link |
HMDB01565 |
| METLIN ID |
6326 |
| PubChem Compound |
1014 |
| PDB ID |
PC |
| ChEBI ID |
18132 |
| 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 |
- 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
- 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
- Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5.
Pubmed: 25935
- 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
- 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
- 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
- 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
- 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
- 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
- Nakabayashi N, Iwasaki Y: Copolymers of 2-methacryloyloxyethyl phosphorylcholine (MPC) as biomaterials. Biomed Mater Eng. 2004;14(4):345-54.
Pubmed: 15472384
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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Normal
