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Identification
YMDB IDYMDB00191
NamePhosphorylcholine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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 a moderately acidic compound (based on its pKa). Phosphorylcholine exists in all living species, ranging from bacteria to humans. Within yeast, phosphorylcholine participates in a number of enzymatic reactions. In particular, phosphorylcholine can be biosynthesized from choline through the action of the enzyme choline kinase. In addition, phosphorylcholine and cytidine triphosphate can be converted into CDP-choline; which is catalyzed by the enzyme choline-phosphate cytidylyltransferase. In yeast, phosphorylcholine is involved in the metabolic pathway called the lysolipid incorporation into er pc(18:1(9z)/18:1(9z)) pathway.
Structure
Thumb
Synonyms
  • Choline phosphate
  • N-Trimethyl-2-aminoethylphosphonate
  • O-Phosphocholine
  • Phosphocholine
  • Phosphoryl-choline
  • CHOP
  • Trimethyl(2-(phosphonooxy)ethyl)ammonium
  • Choline phosphoric acid
  • N-Trimethyl-2-aminoethylphosphonic acid
  • Chloride, phosphorylcholine
  • Phosphate, choline
  • Phosphorylcholine chloride
  • Phosphate chloride, choline
  • Chloride, choline phosphate
  • Choline chloride dihydrogen phosphate
  • Choline phosphate chloride
CAS number3616-04-4
WeightAverage: 184.1507
Monoisotopic: 184.073869485
InChI KeyYHHSONZFOIEMCP-UHFFFAOYSA-O
InChIInChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1
IUPAC Name[2-(trimethylazaniumyl)ethoxy]phosphonic acid
Traditional IUPAC NameChoP
Chemical FormulaC5H15NO4P
SMILES[H]OP(=O)(O[H])OC([H])([H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]
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
Physical Properties
StateSolid
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Choline metabolismPW002494 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ERPW002532 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(10:0/10:0)PW002780 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(14:0/14:0)PW002783 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
Sphingolipid metabolismec00600 Map00600
SMPDB Reactions
SM C18:0 + waterCeramide (d18:1/18:0) + Phosphorylcholine
Choline + Adenosine triphosphateADP + hydron + Phosphorylcholine
Phosphorylcholine + Cytidine triphosphate + hydronCiticoline + Pyrophosphate
KEGG Reactions
Adenosine triphosphate + CholinePhosphorylcholine + hydron + ADP
Phosphorylcholine + hydron + Cytidine triphosphatePyrophosphate + Citicoline
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-cb21d52ab18bca51e777JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-3d961174f1a27a76e351JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9300000000-fff62078da4bf8f84753JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-007a-9000000000-275c66ca16bdb9344ee2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-1dbd5123486fc544909bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001r-4900000000-a77ea15e15088c9209feJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-002r-9600000000-55422f402ca1581e8111JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0072-9100000000-80e4e45c1a0a5ef016ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-006t-9000000000-347eed4168ee48195753JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0040-6900000000-8bbb64f5a93a59787a0dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-9700000000-1e35f21857e363fec75aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-9700000000-1e35f21857e363fec75aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-1dbd5123486fc544909bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001r-4900000000-2fd51d187f11ab05dd9fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-002r-9600000000-57b8ad3f9f3c91e92bdfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0072-9100000000-80e4e45c1a0a5ef016ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006t-9000000000-347eed4168ee48195753JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0040-6900000000-8bbb64f5a93a59787a0dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-9500000000-7b0806b933e054fe2fc1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-9200000000-8134826bf94ee033006dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-b75c9abd7c4ad9a57776JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Kim, K., Kim, K. H., Storey, M. K., Voelker, D. R., Carman, G. M. (1999). "Isolation and characterization of the Saccharomyces cerevisiae EKI1 gene encoding ethanolamine kinase." J Biol Chem 274:14857-14866.10329685
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
External Links:
ResourceLink
CHEBI ID18132
HMDB IDHMDB01565
Pubchem Compound ID1014
Kegg IDC00588
ChemSpider ID73580
FOODB IDFDB022692
WikipediaPhosphorylcholine
BioCyc IDPHOSPHORYL-CHOLINE

Enzymes

General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Responsible for phosphatidylcholine synthesis via the CDP-choline pathway. Also exhibits ethanolamine kinase activity but at 14% efficiency compared with choline
Gene Name:
CKI1
Uniprot ID:
P20485
Molecular weight:
66316.0
Reactions
ATP + choline → ADP + O-phosphocholine.
General function:
Involved in catalytic activity
Specific function:
CTP + choline phosphate = diphosphate + CDP- choline
Gene Name:
PCT1
Uniprot ID:
P13259
Molecular weight:
49405.80078
Reactions
CTP + choline phosphate → diphosphate + CDP-choline.