Livestock Metabolome Database: Showing metabocard for Choline (LMDB00041)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:41:04 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB00041

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Choline

Description

Choline is a basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism. Choline is now considered to be an essential vitamin. While animals can synthesize small amounts (by converting phosphatidylethanolamine to phosphatidylcholine), it must be consumed in the diet to maintain health. Required levels are between 425 mg/day (female) and 550 mg/day (male). Milk, eggs, liver and peanuts are especially rich in choline. Most choline is found in phospholipids, namely phosphatidylcholine or lecithin. Choline can be oxidized to form betaine, which is a methyl source for many reactions (i.e. conversion of homocysteine e to methionine). Lack of sufficient amounts of choline in the diet can lead to a fatty liver condition and general liver damage. This arises from the lack of VLDL, which is necessary to transport fats away from the liver. Choline deficiency also leads to elevated serum levels of alanine amino transferase and is associated with increased incidence of liver cancer.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Bilineurine	ChEBI
CHOLINE ion	ChEBI
N,N,N-Trimethylethanol-ammonium	ChEBI
N-Trimethylethanolamine	ChEBI
Trimethylethanolamine	ChEBI
Choline cation	Kegg
(2-Hydroxyethyl)trimethyl ammonium	HMDB
(2-Hydroxyethyl)trimethylammonium	HMDB
(beta-Hydroxyethyl)trimethylammonium	HMDB
2-Hydroxy-N,N,N-trimethyl-ethanaminium	HMDB
2-Hydroxy-N,N,N-trimethylethanaminium	HMDB
Biocolina	HMDB
Biocoline	HMDB
Cholinum	HMDB
Hepacholine	HMDB
Hormocline	HMDB
Lipotril	HMDB
N,N,N-Trimethylethanolammonium	HMDB
Neocolina	HMDB
Paresan	HMDB
Choline O-sulfate	HMDB
Citrate, choline	HMDB
Fagine	HMDB
Hydroxide, choline	HMDB
Vidine	HMDB
Bursine	HMDB
Chloride, choline	HMDB
Choline chloride	HMDB
Choline citrate	HMDB
Bitartrate, choline	HMDB
Choline bitartrate	HMDB
Choline hydroxide	HMDB
Choline O sulfate	HMDB
O-Sulfate, choline	HMDB

Chemical Formula

C₅H₁₄NO

Average Molecular Weight

104.1708

Monoisotopic Molecular Weight

104.107539075

IUPAC Name

(2-hydroxyethyl)trimethylazanium

Traditional Name

choline

CAS Registry Number

62-49-7

SMILES

C[N+](C)(C)CCO

InChI Identifier

InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1

InChI Key

OEYIOHPDSNJKLS-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Cholines

Alternative Parents

Substituents

Choline
Tetraalkylammonium salt
1,2-aminoalcohol
Alkanolamine
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic salt
Primary alcohol
Organooxygen compound
Amine
Alcohol
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

cholines (CHEBI:15354 )
Pesticides (C00114 )
a small molecule (CHOLINE )

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	-3.6	ALOGPS
logP	-4.7	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	13.97	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.19 m³·mol⁻¹	ChemAxon
Polarizability	12.57 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	splash10-05fr-9100000000-69389426dd865af031f9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05g0-9300000000-ca1b0086d4882b00b395	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0900000000-ea6f9c1150759c5be6c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-1900000000-cadf16d18f093e9b19d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0bt9-9100000000-a2c328b7da5435b8e467	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-0900000000-6a7b57dbdf4560721722	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0udi-5900000000-87fdeef5275a74e78348	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0w29-5900000000-9b79cc5ff3b1ce17deb1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-9200000000-fe62d5a4fbf492493d60	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0udi-3900000000-0b37e63e9c6b14a2e397	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0900000000-6a7b57dbdf4560721722	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-5900000000-87fdeef5275a74e78348	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0pb9-1900000000-391c1b7859a03e776123	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2900000000-43b0f930ff04f7a48a59	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-9400000000-ab7cc75a8e0d3cc49449	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-0b94edfd44e38b20b8d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9100000000-a738404b52e2f1f6fec1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-c596e40769889223b3dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-c6fab16d1790976560b5	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C 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	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D 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

Bile acid
Brain
Cerebrospinal Fluid (CSF)
Colostrum
Feces
Jejunum
Kidney
Liver
Lung
Meat
Milk
Plasma
Ruminal Fluid
Serum
Synovial Fluid
Urine
Vitreous Humour

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Bile acid	Detected but not Quantified	Not Applicable	Not Available	Porcine	21859467	details
Brain	Detected but not Quantified	Not Applicable	Not Available	Ovine	25959287	details
Cerebrospinal Fluid (CSF)	Detected but not Quantified	Not Applicable	Not Available	Ovine	17510975	details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Feces	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Jejunum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21584308	details
Kidney	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Liver	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Lung	Detected and Quantified	0.19+/-0.02 umol/g	Not Available	Porcine	23412987	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Meat	Detected and Quantified	107.79 +/- 4.65 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	118.5 +/- 13.32 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	125.57 +/- 11.43 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	76.73 +/- 5.28 uM	Not Available	Bovine	20831251	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23497994	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23738862	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25087032	details
Milk	Detected and Quantified	152-479 uM	Not Available	Bovine	22098372	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Milk	Detected and Quantified	150-997 uM	Not Available	Bovine	20338431	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	22370585	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24477039	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24440255	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	21859467	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	23100586	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	19603403	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22673149	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	21496096	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Ruminal Fluid	Detected and Quantified	12.1 +/- 1.8 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	16.9 +/- 8.2 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	23.0 +/- 2.9 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	115 +/- 9.2 uM	Not Available	Caprine	22706048	details
Ruminal Fluid	Detected and Quantified	13 +/- 3 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	16 +/- 2 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	17 +/- 6 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	18 +/- 7 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	18 +/- 7 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	25 +/- 13 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	13.1 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	16.7 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	14.7 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	17.5 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	16.9 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	24.6 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	17.2 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	19.8 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Serum	Detected and Quantified	7.8952 +/- 2.874 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	7.7441 +/- 2.3668 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21942754	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	26020888	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21584308	details
Serum	Detected and Quantified	7.81 +/- 2.2811 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected and Quantified	6.3994 +/- 2.5493 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21429726	details
Serum	Detected and Quantified	13.96 +/- 4.62 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	7.4514 +/- 2.3654 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.4777 +/- 0.8762 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	7.9816 +/- 2.859 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.2584 +/- 3.1113 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.8984 +/- 1.2949 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.8264 +/- 2.2807 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.2969 +/- 2.7357 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	7.5454 +/- 2.5921 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.2179 +/- 1.0886 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.7925 +/- 1.9167 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	10.7332 +/- 2.3738 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.7257 +/- 2.8603 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	7.2833 +/- 2.5375 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.4669 +/- 1.6287 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	11.9085 +/- 3.2081 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.3933 +/- 2.0626 uM	Normal	Ovine	Goldansaz et al.,...	details
Synovial Fluid	Detected but not Quantified	Not Applicable	Not Available	Ovine	25283885	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Vitreous Humour	Detected but not Quantified	Not Applicable	Not Available	Caprine	24845217	details