Record Information
Version1.0
Creation date2011-09-21 00:18:03 UTC
Update date2020-09-17 15:38:59 UTC
Primary IDFDB022692
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 a moderately acidic compound (based on its pKa). The phosphate of choline; and the parent compound of the Phosphorylcholine family. Phosphorylcholine exists in all living species, ranging from bacteria to humans. Within humans, phosphorylcholine participates in a number of enzymatic reactions. In particular, cytidine triphosphate and phosphorylcholine can be converted into CDP-choline through the action of the enzyme choline-phosphate cytidylyltransferase. In addition, phosphorylcholine can be biosynthesized from choline; which is catalyzed by the enzyme choline/ethanolamine kinase. In humans, phosphorylcholine is involved in phosphatidylcholine biosynthesis. Outside of the human body, Phosphorylcholine is found, on average, in the highest concentration within beers. Phosphorylcholine has also been detected, but not quantified in, several different foods, such as lemons, quinces, chinese cabbages, italian oregano, and chinese broccoli. This could make phosphorylcholine a potential biomarker for the consumption of these foods.
CAS Number3616-04-4
Structure
Thumb
Synonyms
SynonymSource
Phosphate, cholineMeSH
Phosphorylcholine chlorideMeSH
PhosphocholineMeSH
Choline phosphate chlorideMeSH
Choline chloride dihydrogen phosphateMeSH
Choline phosphateMeSH
Chloride, choline phosphateMeSH
Chloride, phosphorylcholineMeSH
Phosphate chloride, cholineMeSH
Choline ateChEBI
Choline ic acidGenerator
CHOPChEBI
N-Trimethyl-2-aminoethylonateChEBI
N-Trimethyl-2-aminoethylonic acidGenerator
N-Trimethyl-2-aminoethylphosphonatehmdb
O-OcholineChEBI
O-Phosphocholinehmdb
OCHOLINEChEBI
Oryl-cholineChEBI
OrylcholineChEBI
Phosphoryl-cholinehmdb
Trimethyl(2-(onooxy)ethyl)ammoniumChEBI
Predicted Properties
PropertyValueSource
logP-4.8ChemAxon
pKa (Strongest Acidic)1.15ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.59 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.95 m³·mol⁻¹ChemAxon
Polarizability16.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H15NO4P
IUPAC name2-(trimethylazaniumyl)ethyl hydrogen phosphate
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
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
  • 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
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

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
SpectraNot Available
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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