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Showing metabocard for Choline (BMDB0000097)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:19:35 UTC
Update Date2020-06-04 21:13:11 UTC
MCDB ID BMDB0000097
Secondary Accession Numbers
  • BMDB00097
Metabolite Identification
Common NameCholine
DescriptionCholine, 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
BilineurineChEBI
CHOLINE ionChEBI
N,N,N-Trimethylethanol-ammoniumChEBI
N-TrimethylethanolamineChEBI
TrimethylethanolamineChEBI
Choline cationKegg
(2-Hydroxyethyl)trimethyl ammoniumHMDB
(2-Hydroxyethyl)trimethylammoniumHMDB
(beta-Hydroxyethyl)trimethylammoniumHMDB
2-Hydroxy-N,N,N-trimethyl-ethanaminiumHMDB
2-Hydroxy-N,N,N-trimethylethanaminiumHMDB
BiocolinaHMDB
BiocolineHMDB
CholinumHMDB
HepacholineHMDB
HormoclineHMDB
LipotrilHMDB
N,N,N-TrimethylethanolammoniumHMDB
NeocolinaHMDB
ParesanHMDB
Choline O-sulfateHMDB
Citrate, cholineHMDB
FagineHMDB
Hydroxide, cholineHMDB
VidineHMDB
BursineHMDB
Chloride, cholineHMDB
Choline chlorideHMDB
Choline citrateHMDB
Bitartrate, cholineHMDB
Choline bitartrateHMDB
Choline hydroxideHMDB
Choline O sulfateHMDB
O-Sulfate, cholineHMDB
Chemical FormulaC5H14NO
Average Molecular Weight104.1708
Monoisotopic Molecular Weight104.107539075
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number62-49-7
SMILESNot Available
InChI Identifier
InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1
InChI KeyOEYIOHPDSNJKLS-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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentCholines
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point302 - 303 °C (chloride salt)Not Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected and Quantified107 uM details
Detected and Quantified180 - 479 uM details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected and Quantified150 - 997 uM details
Detected and Quantified152 - 479 uM details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected and Quantified206 +/- 14 uM details
Detected and Quantified242 +/- 10 uM details
Detected and Quantified235 +/- 8 uM details
Detected and Quantified214 +/- 17 uM details
Detected and Quantified298 +/- 146 uM details
Detected and Quantified310 +/- 78 uM details
Detected and Quantified214 +/- 58 uM details
HMDB IDHMDB0000097
DrugBank IDDB00122
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000710
KNApSAcK IDC00007298
Chemspider ID299
KEGG Compound IDC00114
BioCyc IDCHOLINE
BiGG ID33910
Wikipedia LinkCholine
METLIN ID56
PubChem Compound305
PDB IDNot Available
ChEBI ID15354
References
Synthesis ReferenceHasegawa, 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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.
  9. 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.