Milk Composition Database: Showing metabocard for Choline (BMDB0000097)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:19:35 UTC

Update Date

2020-06-04 21:13:11 UTC

MCDB ID

BMDB0000097

Secondary Accession Numbers

BMDB00097

Metabolite Identification

Common Name

Choline

Description

Choline, also known as bilineurine or choline ion, belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation. Choline is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Choline exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Choline exists in all living species, ranging from bacteria to humans. Choline participates in a number of enzymatic reactions, within cattle. In particular, Choline can be biosynthesized from acetylcholine; which is mediated by the enzyme acetylcholinesterase. In addition, Choline can be converted into acetylcholine; which is catalyzed by the enzyme choline O-acetyltransferase. In cattle, choline is involved in the metabolic pathway called phospholipid biosynthesis pathway.

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	302 - 303 °C (chloride salt)	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-9100000000-69389426dd865af031f9	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05g0-9300000000-ca1b0086d4882b00b395	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0900000000-ea6f9c1150759c5be6c7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-1900000000-cadf16d18f093e9b19d6	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0bt9-9100000000-a2c328b7da5435b8e467	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-0900000000-6a7b57dbdf4560721722	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0udi-5900000000-87fdeef5275a74e78348	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0w29-5900000000-9b79cc5ff3b1ce17deb1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-9200000000-fe62d5a4fbf492493d60	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0udi-3900000000-0b37e63e9c6b14a2e397	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0900000000-6a7b57dbdf4560721722	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-5900000000-87fdeef5275a74e78348	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0pb9-1900000000-391c1b7859a03e776123	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2900000000-43b0f930ff04f7a48a59	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-9400000000-ab7cc75a8e0d3cc49449	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-0b94edfd44e38b20b8d3	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9100000000-a738404b52e2f1f6fec1	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-c596e40769889223b3dd	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-c6fab16d1790976560b5	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	107 uM	PMID: 3944656	details
Detected and Quantified	180 - 479 uM	PMID: 22098372	details
Detected but not Quantified	Not Applicable	PMID: 23497994	details
Detected but not Quantified	Not Applicable	PMID: 23738862	details
Detected but not Quantified	Not Applicable	PMID: 25087032	details
Detected and Quantified	150 - 997 uM	PMID: 20338431	details
Detected and Quantified	152 - 479 uM	PMID: 22098372	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	206 +/- 14 uM	PMID: 30994344	details
Detected and Quantified	242 +/- 10 uM	PMID: 30994344	details
Detected and Quantified	235 +/- 8 uM	PMID: 30994344	details
Detected and Quantified	214 +/- 17 uM	PMID: 30994344	details
Detected and Quantified	298 +/- 146 uM	PMID: 29642378	details
Detected and Quantified	310 +/- 78 uM	PMID: 29642378	details
Detected and Quantified	214 +/- 58 uM	PMID: 29642378	details

External Links

HMDB ID

HMDB0000097

DrugBank ID

DB00122

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

305

PDB ID

Not Available

ChEBI ID

15354

References

Synthesis Reference

Hasegawa, Yoichi; Hyoda, Shunji; Sawada, Hirotoshi; Baba, Masakatsu. Preparation of high-purity organic carboxylic acid choline salts and choline. Jpn. Kokai Tokkyo Koho (1999), 9 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Zeisel SH, Char D, Sheard NF: Choline, phosphatidylcholine and sphingomyelin in human and bovine milk and infant formulas. J Nutr. 1986 Jan;116(1):50-8. doi: 10.1093/jn/116.1.50. [PubMed:3944656 ]
Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for Choline (BMDB0000097)

Structure for BMDB0000097 (Choline)