Showing Compound Phosphorylcholine (FDB022692)

Record Information

Version

1.0

Creation date

2011-09-21 00:18:03 UTC

Update date

2020-09-17 15:38:59 UTC

Primary ID

FDB022692

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Phosphorylcholine

Description

Phosphorylcholine, 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 Number

3616-04-4

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Phosphate, choline	MeSH
Phosphorylcholine chloride	MeSH
Phosphocholine	MeSH
Choline phosphate chloride	MeSH
Choline chloride dihydrogen phosphate	MeSH
Choline phosphate	MeSH
Chloride, choline phosphate	MeSH
Chloride, phosphorylcholine	MeSH
Phosphate chloride, choline	MeSH
Choline ate	ChEBI
Choline ic acid	Generator
CHOP	ChEBI
N-Trimethyl-2-aminoethylonate	ChEBI
N-Trimethyl-2-aminoethylonic acid	Generator
N-Trimethyl-2-aminoethylphosphonate	hmdb
O-Ocholine	ChEBI
O-Phosphocholine	hmdb
OCHOLINE	ChEBI
Oryl-choline	ChEBI
Orylcholine	ChEBI
Phosphoryl-choline	hmdb
Trimethyl(2-(onooxy)ethyl)ammonium	ChEBI

Predicted Properties

Property	Value	Source
logP	-4.8	ChemAxon
pKa (Strongest Acidic)	1.15	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.95 m³·mol⁻¹	ChemAxon
Polarizability	16.93 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C5H15NO4P

IUPAC name

2-(trimethylazaniumyl)ethyl hydrogen phosphate

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 Key

YHHSONZFOIEMCP-UHFFFAOYSA-O

Isomeric SMILES

C[N+](C)(C)CCOP(O)(O)=O

Average Molecular Weight

184.1507

Monoisotopic Molecular Weight

184.073869485

Classification

Description

Belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Phosphocholines

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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect:

Health condition:

Multi-infarct dementia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18132

Phenol-Explorer ID

Not Available

DrugBank ID

DB03945

HMDB ID

HMDB01565

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

48308

KNApSAcK ID

Not Available

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Phosphorylcholine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Choline-phosphate cytidylyltransferase B	PCYT1B	Q9Y5K3
Choline-phosphate cytidylyltransferase A	PCYT1A	P49585
Choline/ethanolamine kinase	CHKB	Q9Y259
Choline kinase alpha	CHKA	P35790
Ectonucleotide pyrophosphatase/phosphodiesterase family member 6	ENPP6	Q6UWR7
Sphingomyelin phosphodiesterase	SMPD1	P17405