Record Information
Version2.0
Creation Date2012-05-31 09:57:14 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00097
Identification
Name:Choline
Description:Choline is a trimethylammonium compound. Choine can be used as a substrate by bacteria to generate osmoprotectants. Choline dehydrogenase (CHD) catalyzes the first step in the biosynthesis of the osmoprotectant glycine betaine from choline. CHD is associated with the membrane, is electron transfer-linked and oxygen dependent.
Structure
Thumb
Synonyms:
  • (2-Hydroxyethyl)trimethyl ammonium
  • (2-Hydroxyethyl)trimethylammonium
  • (b-Hydroxyethyl)trimethylammonium
  • (beta-hydroxyethyl)trimethylammonium
  • (β-Hydroxyethyl)trimethylammonium
  • 2-Hydroxy-N,N,N-trimethyl-ethanaminium
  • 2-Hydroxy-N,N,N-trimethylethanaminium
  • Bilineurine
  • Biocolina
  • Biocoline
  • Choline
  • Choline cation
  • Choline ion
  • Cholinum
  • Hepacholine
  • Hormocline
  • Lipotril
  • N,N,N-Trimethylethanol-ammonium
  • N,N,N-Trimethylethanolammonium
  • Neocolina
  • Paresan
Chemical Formula:C5H14NO
Weight:Average: 104.1708
Monoisotopic: 104.107539075
InChI Key:OEYIOHPDSNJKLS-UHFFFAOYSA-N
InChI:InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1
CAS number:62-49-7
IUPAC Name:(2-hydroxyethyl)trimethylazanium
Traditional IUPAC Name:choline
SMILES:C[N+](C)(C)CCO
Chemical Taxonomy
DescriptionThis compound 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
State:Solid
Charge:1
Melting point:302-303 °C (Chloride salt)
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.61 mg/mLALOGPS
logP-3.6ALOGPS
logP-4.7ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)13.97ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.19 m3·mol-1ChemAxon
Polarizability12.57 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:
  • glycine betaine biosynthesis I (Gram-negative bacteria) BETSYN-PWY
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-05fr-9100000000-69389426dd865af031f9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-05g0-9300000000-ca1b0086d4882b00b395View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0900000000-ea6f9c1150759c5be6c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-1900000000-cadf16d18f093e9b19d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0bt9-9100000000-a2c328b7da5435b8e467View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-6a7b57dbdf4560721722View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0udi-5900000000-87fdeef5275a74e78348View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0w29-5900000000-9b79cc5ff3b1ce17deb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9200000000-fe62d5a4fbf492493d60View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-3900000000-0b37e63e9c6b14a2e397View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-6a7b57dbdf4560721722View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-5900000000-87fdeef5275a74e78348View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0pb9-1900000000-391c1b7859a03e776123View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-43b0f930ff04f7a48a59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-9400000000-ab7cc75a8e0d3cc49449View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-0b94edfd44e38b20b8d3View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Babb SM, Ke Y, Lange N, Kaufman MJ, Renshaw PF, Cohen BM: Oral choline increases choline metabolites in human brain. Psychiatry Res. 2004 Jan 15;130(1):1-9. Pubmed: 14972364
  • Buchman AL, Ament ME, Sohel M, Dubin M, Jenden DJ, Roch M, Pownall H, Farley W, Awal M, Ahn C: Choline deficiency causes reversible hepatic abnormalities in patients receiving parenteral nutrition: proof of a human choline requirement: a placebo-controlled trial. JPEN J Parenter Enteral Nutr. 2001 Sep-Oct;25(5):260-8. Pubmed: 11531217
  • Chen CY, Li CW, Kuo YT, Jaw TS, Wu DK, Jao JC, Hsu JS, Liu GC: Early response of hepatocellular carcinoma to transcatheter arterial chemoembolization: choline levels and MR diffusion constants--initial experience. Radiology. 2006 May;239(2):448-56. Epub 2006 Mar 28. Pubmed: 16569781
  • da Costa KA, Badea M, Fischer LM, Zeisel SH: Elevated serum creatine phosphokinase in choline-deficient humans: mechanistic studies in C2C12 mouse myoblasts. Am J Clin Nutr. 2004 Jul;80(1):163-70. Pubmed: 15213044
  • Farsad M, Schiavina R, Castellucci P, Nanni C, Corti B, Martorana G, Canini R, Grigioni W, Boschi S, Marengo M, Pettinato C, Salizzoni E, Monetti N, Franchi R, Fanti S: Detection and localization of prostate cancer: correlation of (11)C-choline PET/CT with histopathologic step-section analysis. J Nucl Med. 2005 Oct;46(10):1642-9. Pubmed: 16204714
  • Garner SC, Chou SC, Mar MH, Coleman RA, Zeisel SH: Characterization of choline metabolism and secretion by human placental trophoblasts in culture. Biochim Biophys Acta. 1993 Jul 1;1168(3):358-64. Pubmed: 8323976
  • Ilcol YO, Donmez O, Yavuz M, Dilek K, Yurtkuran M, Ulus IH: Free choline and phospholipid-bound choline concentrations in serum and dialysate during peritoneal dialysis in children and adults. Clin Biochem. 2002 Jun;35(4):307-13. Pubmed: 12135694
  • Jacob RA, Jenden DJ, Allman-Farinelli MA, Swendseid ME: Folate nutriture alters choline status of women and men fed low choline diets. J Nutr. 1999 Mar;129(3):712-7. Pubmed: 10082779
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Katz-Brull R, Margalit R, Degani H: Differential routing of choline in implanted breast cancer and normal organs. Magn Reson Med. 2001 Jul;46(1):31-8. Pubmed: 11443708
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kohlmeier M, da Costa KA, Fischer LM, Zeisel SH: Genetic variation of folate-mediated one-carbon transfer pathway predicts susceptibility to choline deficiency in humans. Proc Natl Acad Sci U S A. 2005 Nov 1;102(44):16025-30. Epub 2005 Oct 18. Pubmed: 16236726
  • Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. Pubmed: 7762816
  • Ozarda Ilcol Y, Ozyurt G, Kilicturgay S, Uncu G, Ulus IH: The decline in serum choline concentration in humans during and after surgery is associated with the elevation of cortisol, adrenocorticotropic hormone, prolactin and beta-endorphin concentrations. Neurosci Lett. 2002 May 10;324(1):41-4. Pubmed: 11983290
  • Pal K, Sharma U, Gupta DK, Pratap A, Jagannathan NR: Metabolite profile of cerebrospinal fluid in patients with spina bifida: a proton magnetic resonance spectroscopy study. Spine. 2005 Feb 1;30(3):E68-72. Pubmed: 15681999
  • Rumpel H, Ho GL, Chan LL, Lim WE, Chong VF: Concomitant diminishing magnetization-transfer effect and increasing choline level in radiation-induced temporal-lobe changes. Australas Radiol. 2002 Sep;46(3):340-4. Pubmed: 12196251
  • Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Van Hove JL, Lazeyras F, Zeisel SH, Bottiglieri T, Hyland K, Charles HC, Gray L, Jaeken J, Kahler SG: One-methyl group metabolism in non-ketotic hyperglycinaemia: mildly elevated cerebrospinal fluid homocysteine levels. J Inherit Metab Dis. 1998 Dec;21(8):799-811. Pubmed: 9870205
  • Walter A, Korth U, Hilgert M, Hartmann J, Weichel O, Hilgert M, Fassbender K, Schmitt A, Klein J: Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Neurobiol Aging. 2004 Nov-Dec;25(10):1299-303. Pubmed: 15465626
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yanagawa T, Watanabe H, Inoue T, Ahmed AR, Tomiyoshi K, Shinozaki T, Oriuchi N, Endo K, Takagishi K: Carbon-11 choline positron emission tomography in musculoskeletal tumors: comparison with fluorine-18 fluorodeoxyglucose positron emission tomography. J Comput Assist Tomogr. 2003 Mar-Apr;27(2):175-82. Pubmed: 12703009
  • Zeisel SH: Choline: critical role during fetal development and dietary requirements in adults. Annu Rev Nutr. 2006;26:229-50. Pubmed: 16848706
  • Zeisel SH: Nutritional importance of choline for brain development. J Am Coll Nutr. 2004 Dec;23(6 Suppl):621S-626S. Pubmed: 15640516
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)
External Links:
ResourceLink
CHEBI ID15354
HMDB IDHMDB00097
Pubchem Compound ID305
Kegg IDC00114
ChemSpider ID299
WikipediaCholine
BioCyc IDCHOLINE
EcoCyc IDCHOLINE
Ligand ExpoCHT

Enzymes

General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
glpQ
Uniprot ID:
P09394
Molecular weight:
40843
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
ugpQ
Uniprot ID:
P10908
Molecular weight:
27409
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in choline dehydrogenase activity
Specific function:
Can catalyze the oxidation of choline to betaine aldehyde and betaine aldehyde to glycine betaine at the same rate
Gene Name:
betA
Uniprot ID:
P17444
Molecular weight:
61877
Reactions
Choline + acceptor = betaine aldehyde + reduced acceptor.
General function:
Involved in transporter activity
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
yehW
Uniprot ID:
P33359
Molecular weight:
25514
General function:
Involved in transporter activity
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
yehY
Uniprot ID:
P33361
Molecular weight:
41138
General function:
Involved in nucleotide binding
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for energy coupling to the transport system
Gene Name:
yehX
Uniprot ID:
P33360
Molecular weight:
34424
General function:
Involved in transporter activity
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules
Gene Name:
osmF
Uniprot ID:
P33362
Molecular weight:
32609

Transporters

General function:
Involved in transporter activity
Specific function:
Probable transporter whose substrate is unknown. Is not involved in aerobic D-malate transport
Gene Name:
yeaV
Uniprot ID:
P0ABD1
Molecular weight:
52881
General function:
Involved in transporter activity
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
yehW
Uniprot ID:
P33359
Molecular weight:
25514
General function:
Involved in transporter activity
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
yehY
Uniprot ID:
P33361
Molecular weight:
41138
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
High-affinity uptake of choline driven by a proton- motive force
Gene Name:
betT
Uniprot ID:
P0ABC9
Molecular weight:
75842
General function:
Involved in nucleotide binding
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for energy coupling to the transport system
Gene Name:
yehX
Uniprot ID:
P33360
Molecular weight:
34424
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules
Gene Name:
osmF
Uniprot ID:
P33362
Molecular weight:
32609
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368