Record Information
Version1.0
Creation date2011-09-21 00:18:03 UTC
Update date2018-05-28 18:33:34 UTC
Primary IDFDB022692
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhosphorylcholine
DescriptionPhosphorylcholine 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). [HMDB]
CAS Number3616-04-4
Structure
Thumb
Synonyms
SynonymSource
Choline phosphateChEBI
CHOPChEBI
N-Trimethyl-2-aminoethylphosphonateChEBI
O-PhosphocholineChEBI
Phosphoryl-cholineChEBI
Trimethyl(2-(phosphonooxy)ethyl)ammoniumChEBI
Choline phosphoric acidGenerator
N-Trimethyl-2-aminoethylphosphonic acidGenerator
PhosphocholineHMDB
Chloride, phosphorylcholineMeSH
Phosphate, cholineMeSH
Phosphorylcholine chlorideMeSH
Phosphate chloride, cholineMeSH
Chloride, choline phosphateMeSH
Choline chloride dihydrogen phosphateMeSH
Choline phosphate chlorideMeSH
Choline ateChEBI
Choline ic acidGenerator
N-Trimethyl-2-aminoethylonateChEBI
N-Trimethyl-2-aminoethylonic acidGenerator
O-OcholineChEBI
OCHOLINEChEBI
Oryl-cholineChEBI
OrylcholineChEBI
Trimethyl(2-(onooxy)ethyl)ammoniumChEBI
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
Chemical FormulaC5H15NO4P
IUPAC name[2-(trimethylazaniumyl)ethoxy]phosphonic acid
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
Isomeric SMILESC[N+](C)(C)CCOP(O)(O)=O
Average Molecular Weight184.1507
Monoisotopic Molecular Weight184.073869485
Classification
DescriptionThis compound belongs to the class of organic compounds known as phosphocholines. These 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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
ChemSpider ID989
ChEMBL IDCHEMBL1235161
KEGG Compound IDC00588
Pubchem Compound ID1014
Pubchem Substance IDNot Available
ChEBI ID18132
Phenol-Explorer IDNot Available
DrugBank IDDB03945
HMDB IDHMDB01565
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID48308
KNApSAcK IDNot Available
HET IDPC
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPhosphorylcholine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Choline-phosphate cytidylyltransferase BPCYT1BQ9Y5K3
Choline-phosphate cytidylyltransferase APCYT1AP49585
Choline/ethanolamine kinaseCHKBQ9Y259
Choline kinase alphaCHKAP35790
Ectonucleotide pyrophosphatase/phosphodiesterase family member 6ENPP6Q6UWR7
Sphingomyelin phosphodiesteraseSMPD1P17405
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference