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Record Information
Version1.0
Creation Date2016-09-30 22:47:44 UTC
Update Date2020-06-04 20:32:23 UTC
BMDB IDBMDB0001565
Secondary Accession Numbers
  • BMDB01565
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. Phosphorylcholine is possibly soluble (in water) and a moderately acidic compound (based on its pKa). Phosphorylcholine exists in all living species, ranging from bacteria to humans. Phosphorylcholine participates in a number of enzymatic reactions, within cattle. In particular, Cytidine triphosphate and phosphorylcholine can be converted into CDP-choline; which is catalyzed by the enzyme choline-phosphate cytidylyltransferase. In addition, Phosphorylcholine can be biosynthesized from choline; which is mediated by the enzyme choline/ethanolamine kinase. In cattle, phosphorylcholine is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(16:0/16:0) pathway.
Structure
Thumb
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
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-cb21d52ab18bca51e777View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-3d961174f1a27a76e351View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9300000000-fff62078da4bf8f84753View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-007a-9000000000-275c66ca16bdb9344ee2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-1dbd5123486fc544909bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001r-4900000000-a77ea15e15088c9209feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-002r-9600000000-55422f402ca1581e8111View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0072-9100000000-80e4e45c1a0a5ef016ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-006t-9000000000-347eed4168ee48195753View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0040-6900000000-8bbb64f5a93a59787a0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-9700000000-1e35f21857e363fec75aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-9700000000-1e35f21857e363fec75aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-1dbd5123486fc544909bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001r-4900000000-2fd51d187f11ab05dd9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-002r-9600000000-57b8ad3f9f3c91e92bdfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0072-9100000000-80e4e45c1a0a5ef016ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006t-9000000000-347eed4168ee48195753View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0040-6900000000-8bbb64f5a93a59787a0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-9500000000-7b0806b933e054fe2fc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-9200000000-8134826bf94ee033006dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-b75c9abd7c4ad9a57776View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Milk
  • Placenta
  • Platelet
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected and Quantified1658 +/- 593 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified72.12 +/- 59.74 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified143 - 1355 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified183 - 941 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified30.83 +/- 34.97 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified44.14 +/- 32.01 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified122 +/- 8 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified123 +/- 7 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified116 +/- 7 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified120 +/- 1 uMNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisDetected and Quantified1058 +/- 234 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001565
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
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)Not Available
General References
  1. 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. [PubMed:20338431 ]
  2. 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. [PubMed:22098372 ]
  3. 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. [PubMed:23182357 ]
  4. 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. [PubMed:25087032 ]
  5. 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. [PubMed:23738862 ]
  6. 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. [PubMed:29642378 ]
  7. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Involved in hydrolase activity, acting on glycosyl bonds
Specific function:
Converts sphingomyelin to ceramide. Also has phospholipase C activities toward 1,2-diacylglycerolphosphocholine and 1,2-diacylglycerolphosphoglycerol.
Gene Name:
SMPD1
Uniprot ID:
Q0VD19
Molecular weight:
69392.0
General function:
Involved in ADP-ribose diphosphatase activity
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:
A7YY53
Molecular weight:
39235.0
General function:
Involved in magnesium ion binding
Specific function:
Phosphatase that has high activity toward pyridoxal 5'-phosphate (PLP). Also active at much lower level toward pyrophosphate, phosphoethanolamine (PEA), phosphocholine (PCho), phospho-l-tyrosine, fructose-6-phosphate, p-nitrophenyl phosphate, and h-glycerophosphate (By similarity).
Gene Name:
PHOSPHO2
Uniprot ID:
Q2KI06
Molecular weight:
27751.0
Reactions
Phosphorylcholine → Cholinedetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine (By similarity).
Gene Name:
PCYT2
Uniprot ID:
Q5EA75
Molecular weight:
44158.0
Reactions
Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + Citicolinedetails
Phosphorylcholine → Citicolinedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
CHKA
Uniprot ID:
F1MI39
Molecular weight:
64756.0
Reactions
Choline + Adenosine triphosphate → Phosphorylcholine + ADPdetails
Choline → Phosphorylcholinedetails