Phosphorylcholine (CHEM022410)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:31:47 UTC
Update Date2016-11-09 01:17:30 UTC
Accession NumberCHEM022410
Identification
Common NamePhosphorylcholine
ClassSmall Molecule
DescriptionThe phosphate of choline; and the parent compound of the phosphocholine family.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass184.151 g/mol
Monoisotopic Mass184.074 g/mol
CAS Registry Number3616-04-4
IUPAC Name[2-(trimethylazaniumyl)ethoxy]phosphonic acid
Traditional NameChoP
SMILESC[N+](C)(C)CCOP(O)(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 Area66.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.07 m³·mol⁻¹ChemAxon
Polarizability17.23 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-cb21d52ab18bca51e777Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-3d961174f1a27a76e351Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9300000000-fff62078da4bf8f84753Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-007a-9000000000-275c66ca16bdb9344ee2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-1dbd5123486fc544909bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001r-4900000000-a77ea15e15088c9209feSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-002r-9600000000-55422f402ca1581e8111Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0072-9100000000-80e4e45c1a0a5ef016ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-006t-9000000000-347eed4168ee48195753Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0040-6900000000-8bbb64f5a93a59787a0dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-9700000000-1e35f21857e363fec75aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-9700000000-1e35f21857e363fec75aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-1dbd5123486fc544909bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001r-4900000000-2fd51d187f11ab05dd9fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-002r-9600000000-57b8ad3f9f3c91e92bdfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0072-9100000000-80e4e45c1a0a5ef016ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006t-9000000000-347eed4168ee48195753Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0040-6900000000-8bbb64f5a93a59787a0dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-3900000000-d64b56779c67fb13738dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00ds-9200000000-e65557cea0495452a5beSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-4900000000-4d34ff6b3e7ac6a8a67aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000t-9000000000-a00e7417eed2c9707fe5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-08400ca570d2f786b4dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-9500000000-7b0806b933e054fe2fc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-9200000000-8134826bf94ee033006dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-b75c9abd7c4ad9a57776Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB03945
HMDB IDHMDB0001565
FooDB IDFDB031111
Phenol Explorer IDNot Available
KNApSAcK IDC00007299
BiGG ID48308
BioCyc IDPHOSPHORYL-CHOLINE
METLIN ID6326
PDB IDNot Available
Wikipedia LinkPhosphorylcholine
Chemspider ID989
ChEBI ID18132
PubChem Compound ID1014
Kegg Compound IDC00588
YMDB IDYMDB00191
ECMDB IDM2MDB004152
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10456913
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10596404
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=10811914
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11437497
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11908950
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15267227
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15583011
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18684852
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19369878
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=19748321
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19758165
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23572077
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24012478
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=6420466
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=6790611
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=7450902
17. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.
18. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.
19. Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.
20. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.
21. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.
22. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.
23. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
24. 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
25. 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.
26. 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.
27. Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5.
28. 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.
29. 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.
30. 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.
31. 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.
32. 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.
33. 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.
34. Nakabayashi N, Iwasaki Y: Copolymers of 2-methacryloyloxyethyl phosphorylcholine (MPC) as biomaterials. Biomed Mater Eng. 2004;14(4):345-54.
35. 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.
36. 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.
37. 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.
38. 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.
39. 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.
40. 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.
41. 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.
42. 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.
43. 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.
44. 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.
45. 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.
46. 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.