Cannabis Compound Database: Showing Compound Card for Phosphorylcholine (CDB004925)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (12) Show 18 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:51:07 UTC

Updated at

2020-12-07 19:11:17 UTC

CannabisDB ID

CDB004925

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common 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. Phosphorylcholine is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

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

Synonyms

Value	Source
Choline phosphate	ChEBI
CHOP	ChEBI
N-Trimethyl-2-aminoethylphosphonate	ChEBI
O-Phosphocholine	ChEBI
Phosphoryl-choline	ChEBI
Trimethyl(2-(phosphonooxy)ethyl)ammonium	ChEBI
Phosphocholine	Kegg
Choline phosphoric acid	Generator
N-Trimethyl-2-aminoethylphosphonic acid	Generator
Chloride, phosphorylcholine	HMDB
Phosphate, choline	HMDB
Phosphorylcholine chloride	HMDB
Phosphate chloride, choline	HMDB
Chloride, choline phosphate	HMDB
Choline chloride dihydrogen phosphate	HMDB
Choline phosphate chloride	HMDB

Chemical Formula

C₅H₁₅NO₄P

Average Molecular Weight

184.15

Monoisotopic Molecular Weight

184.0739

IUPAC Name

[2-(trimethylazaniumyl)ethoxy]phosphonic acid

Traditional Name

ChoP

CAS Registry Number

3616-04-4

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 Key

YHHSONZFOIEMCP-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Phosphocholines

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 Framework

Aliphatic acyclic compounds

External Descriptors

phosphocholines (CHEBI:18132 )

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

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.4	ALOGPS
logP	-4.8	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.15	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	53.07 m³·mol⁻¹	ChemAxon
Polarizability	17.23 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Phosphorylcholine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9100000000-cb21d52ab18bca51e777	Spectrum
Predicted GC-MS	Phosphorylcholine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-3d961174f1a27a76e351	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9300000000-fff62078da4bf8f84753	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-007a-9000000000-275c66ca16bdb9344ee2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-0900000000-1dbd5123486fc544909b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001r-4900000000-a77ea15e15088c9209fe	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-002r-9600000000-55422f402ca1581e8111	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0072-9100000000-80e4e45c1a0a5ef016ce	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-006t-9000000000-347eed4168ee48195753	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0040-6900000000-8bbb64f5a93a59787a0d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-9700000000-1e35f21857e363fec75a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-9700000000-1e35f21857e363fec75a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-1dbd5123486fc544909b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001r-4900000000-2fd51d187f11ab05dd9f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-002r-9600000000-57b8ad3f9f3c91e92bdf	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0072-9100000000-80e4e45c1a0a5ef016ce	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-006t-9000000000-347eed4168ee48195753	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0040-6900000000-8bbb64f5a93a59787a0d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-3900000000-d64b56779c67fb13738d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00ds-9200000000-e65557cea0495452a5be	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-4900000000-4d34ff6b3e7ac6a8a67a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000t-9000000000-a00e7417eed2c9707fe5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-08400ca570d2f786b4db	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001r-9500000000-7b0806b933e054fe2fc1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001r-9200000000-8134826bf94ee033006d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-b75c9abd7c4ad9a57776	2017-09-01	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phospholipid Biosynthesis
Sphingolipid Metabolism
Gaucher Disease		Not Available
Globoid Cell Leukodystrophy		Not Available
Metachromatic Leukodystrophy (MLD)		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Choline-phosphate cytidylyltransferase B	PCYT1B	Xp22.11	Q9Y5K3	details
Choline-phosphate cytidylyltransferase A	PCYT1A	3q29	P49585	details
Sphingomyelin phosphodiesterase	SMPD1	11p15.4-p15.1	P17405	details
Choline/ethanolamine kinase	CHKB	22q13.33	Q9Y259	details
Choline kinase alpha	CHKA	11q13.2	P35790	details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 7	ENPP7	17q25.3	Q6UWV6	details
Sphingomyelin phosphodiesterase 2	SMPD2	6q21	O60906	details
Phosphoethanolamine/phosphocholine phosphatase	PHOSPHO1	17q21.32	Q8TCT1	details
Sphingomyelin phosphodiesterase 3	SMPD3	16q22.1	Q9NY59	details
Sphingomyelin phosphodiesterase 4	SMPD4	2q21.1	Q9NXE4	details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 6	ENPP6	4q35.1	Q6UWR7	details
Manganese-dependent ADP-ribose/CDP-alcohol diphosphatase	ADPRM	17p13.1	Q3LIE5	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Sphingomyelin phosphodiesterase 2	SMPD2	6q21	O60906	details
Phosphoethanolamine/phosphocholine phosphatase	PHOSPHO1	17q21.32	Q8TCT1	details
Sphingomyelin phosphodiesterase 3	SMPD3	16q22.1	Q9NY59	details
Sphingomyelin phosphodiesterase 4	SMPD4	2q21.1	Q9NXE4	details
Manganese-dependent ADP-ribose/CDP-alcohol diphosphatase	ADPRM	17p13.1	Q3LIE5	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Sphingomyelin phosphodiesterase 2	SMPD2	6q21	O60906	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001565

DrugBank ID

DB03945

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

18132

References

General References

Not Available

Only showing the first 10 proteins. There are 18 proteins in total.

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Enzymes

Enzyme Details

1. Choline-phosphate cytidylyltransferase B

General function:: Involved in catalytic activity
Specific function:: Controls phosphatidylcholine synthesis.
Gene Name:: PCYT1B
Uniprot ID:: Q9Y5K3
Molecular weight:: 40228.99

Enzyme Details

2. Choline-phosphate cytidylyltransferase A

General function:: Involved in catalytic activity
Specific function:: Controls phosphatidylcholine synthesis.
Gene Name:: PCYT1A
Uniprot ID:: P49585
Molecular weight:: 41730.67

Enzyme Details

3. Sphingomyelin phosphodiesterase

General function:: Involved in hydrolase activity
Specific function:: Converts sphingomyelin to ceramide. Also has phospholipase C activities toward 1,2-diacylglycerolphosphocholine and 1,2-diacylglycerolphosphoglycerol. Isoform 2 and isoform 3 have lost catalytic activity.
Gene Name:: SMPD1
Uniprot ID:: P17405
Molecular weight:: 69935.53

Enzyme Details

4. Choline/ethanolamine kinase

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Has a key role in phospholipid biosynthesis. Catalyzes the first step in phosphatidylethanolamine biosynthesis. Phosphorylates ethanolamine, and can also act on choline (in vitro). Has higher activity with ethanolamine. May not significantly contribute to in vivo phosphatidylcholine biosynthesis.
Gene Name:: CHKB
Uniprot ID:: Q9Y259
Molecular weight:: 45270.99

Enzyme Details

5. Choline kinase alpha

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Has a key role in phospholipid biosynthesis and may contribute to tumor cell growth. Catalyzes the first step in phosphatidylcholine biosynthesis. Contributes to phosphatidylethanolamine biosynthesis. Phosphorylates choline and ethanolamine. Has higher activity with choline.
Gene Name:: CHKA
Uniprot ID:: P35790
Molecular weight:: 52248.53

Enzyme Details

6. Ectonucleotide pyrophosphatase/phosphodiesterase family member 7

General function:: Involved in catalytic activity
Specific function:: Converts sphingomyelin to ceramide. Also has phospholipase C activity toward palmitoyl lyso-phosphocholine. Does not appear to have nucleotide pyrophosphatase activity.
Gene Name:: ENPP7
Uniprot ID:: Q6UWV6
Molecular weight:: 51493.415

Enzyme Details

7. Sphingomyelin phosphodiesterase 2

General function:: Involved in metal ion binding
Specific function:: Converts sphingomyelin to ceramide. Hydrolyze 1-acyl-2-lyso-sn-glycero-3-phosphocholine (lyso-PC) and 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholine (lyso-platelet-activating factor). The physiological substrate seems to be Lyso-PAF.
Gene Name:: SMPD2
Uniprot ID:: O60906
Molecular weight:: 47645.29

Enzyme Details

8. Phosphoethanolamine/phosphocholine phosphatase

General function:: Involved in phosphatase activity
Specific function:: Phosphatase that has a high activity toward phosphoethanolamine (PEA) and phosphocholine (PCho). Involved in the generation of inorganic phosphate for bone mineralization.
Gene Name:: PHOSPHO1
Uniprot ID:: Q8TCT1
Molecular weight:: 32350.505

Enzyme Details

9. Sphingomyelin phosphodiesterase 3

General function:: Involved in metal ion binding
Specific function:: Catalyzes the hydrolysis of sphingomyelin to form ceramide and phosphocholine. Ceramide mediates numerous cellular functions, such as apoptosis and growth arrest, and is capable of regulating these 2 cellular events independently. Also hydrolyzes sphingosylphosphocholine. Regulates the cell cycle by acting as a growth suppressor in confluent cells. Probably acts as a regulator of postnatal development and participates in bone and dentin mineralization.
Gene Name:: SMPD3
Uniprot ID:: Q9NY59
Molecular weight:: 71080.1

Enzyme Details

10. Sphingomyelin phosphodiesterase 4

General function:: Involved in metal ion binding
Specific function:: Catalyzes the hydrolysis of membrane sphingomyelin to form phosphorylcholine and ceramide.
Gene Name:: SMPD4
Uniprot ID:: Q9NXE4
Molecular weight:: 86192.575

Only showing the first 10 proteins. There are 18 proteins in total.

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Showing Compound Card for Phosphorylcholine (CDB004925)

Structure for CDB004925 (Phosphorylcholine)

Enzymes