Livestock Metabolome Database: Showing metabocard for Phosphorylcholine (LMDB00349)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:47:52 UTC

Update Date

2016-07-20 20:53:09 UTC

Lmdb

LMDB00349

Secondary Accession Numbers

None

Metabolite 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 exists in all living species, ranging from bacteria to plants to humans. In humans, phosphorylcholine is involved in the phosphatidylcholine biosynthesis pathway. Phosphorylcholine is found, on average, in the highest concentration within beer. Phosphorylcholine has also been detected, but not quantified in, several different foods, such as atlantic herrings (Clupea harengus harengus), chervils (Anthriscus cerefolium), spearmints (Mentha spicata), canola, and pears (Pyrus communis). This could make phosphorylcholine a potential biomarker for the consumption of these foods. Phosphorylcholine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Phosphorylcholine.

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

184.1507

Monoisotopic Molecular Weight

184.073869485

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

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9100000000-cb21d52ab18bca51e777	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-3d961174f1a27a76e351	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9300000000-fff62078da4bf8f84753	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-007a-9000000000-275c66ca16bdb9344ee2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-0900000000-1dbd5123486fc544909b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001r-4900000000-a77ea15e15088c9209fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-002r-9600000000-55422f402ca1581e8111	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0072-9100000000-80e4e45c1a0a5ef016ce	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-006t-9000000000-347eed4168ee48195753	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0040-6900000000-8bbb64f5a93a59787a0d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-9700000000-1e35f21857e363fec75a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-9700000000-1e35f21857e363fec75a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-1dbd5123486fc544909b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001r-4900000000-2fd51d187f11ab05dd9f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-002r-9600000000-57b8ad3f9f3c91e92bdf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0072-9100000000-80e4e45c1a0a5ef016ce	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-006t-9000000000-347eed4168ee48195753	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0040-6900000000-8bbb64f5a93a59787a0d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-3900000000-d64b56779c67fb13738d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00ds-9200000000-e65557cea0495452a5be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-4900000000-4d34ff6b3e7ac6a8a67a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000t-9000000000-a00e7417eed2c9707fe5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-08400ca570d2f786b4db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001r-9500000000-7b0806b933e054fe2fc1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001r-9200000000-8134826bf94ee033006d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-b75c9abd7c4ad9a57776	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Liver
Lung
Milk
Plasma
Serum
Synovial Fluid
Urine
Vitreous Humour

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Liver	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Lung	Detected and Quantified	0.42+/-0.03 umol/g	Not Available	Porcine	23412987	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23738862	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23182357	details
Milk	Detected and Quantified	183-941 uM	Not Available	Bovine	22098372	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25087032	details
Milk	Detected and Quantified	143-1355 uM	Not Available	Bovine	20338431	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	23100586	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Synovial Fluid	Detected but not Quantified	Not Applicable	Not Available	Ovine	25283885	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Vitreous Humour	Detected but not Quantified	Not Applicable	Not Available	Caprine	24845217	details

External Links

DrugBank ID

DB03945

HMDB ID

HMDB0001565

FooDB ID

FDB031111

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lochnit G, Dennis RD, Geyer R: Phosphorylcholine substituents in nematodes: structures, occurrence and biological implications. Biol Chem. 2000 Sep-Oct;381(9-10):839-47. [11076016 ]

Showing metabocard for Phosphorylcholine (LMDB00349)

Structure for LMDB00349 (Phosphorylcholine)