Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:53 UTC
HMDB IDHMDB00097
Secondary Accession NumbersNone
Metabolite Identification
Common NameCholine
DescriptionCholine 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 humans 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
Thumb
Synonyms
  1. (2-Hydroxyethyl)trimethyl ammonium
  2. (2-Hydroxyethyl)trimethylammonium
  3. (beta-hydroxyethyl)trimethylammonium
  4. 2-Hydroxy-N,N,N-trimethyl-ethanaminium
  5. 2-Hydroxy-N,N,N-trimethylethanaminium
  6. Bilineurine
  7. Biocolina
  8. Biocoline
  9. Choline
  10. Choline cation
  11. Choline ion
  12. Cholinum
  13. Hepacholine
  14. Hormocline
  15. Lipotril
  16. N,N,N-Trimethylethanol-ammonium
  17. N,N,N-Trimethylethanolammonium
  18. Neocolina
  19. Paresan
Chemical FormulaC5H14NO
Average Molecular Weight104.1708
Monoisotopic Molecular Weight104.107539075
IUPAC Name(2-hydroxyethyl)trimethylazanium
Traditional IUPAC Namecholine
CAS Registry Number62-49-7
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 KeyOEYIOHPDSNJKLS-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlcohols and Polyols
Sub ClassCholines
Other Descriptors
  • Pesticides(KEGG)
  • a small molecule(Cyc)
  • cholines(ChEBI)
Substituents
  • Primary Alcohol
  • Quaternary Ammonium Salt
Direct ParentCholines
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
  • Plant
Biofunction
  • Component of Glycerophospholipid metabolism
  • Component of Glycine, serine and threonine metabolism
  • Component of Glycosphingolipid metabolism
  • Essential vitamins
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Nucleus
  • Endoplasmic reticulum
  • Golgi apparatus
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 Properties
PropertyValueSource
water solubility3.61 g/LALOGPS
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 area20.23ChemAxon
rotatable bond count2ChemAxon
refractivity42.19ChemAxon
polarizability12.57ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Nucleus
  • Endoplasmic reticulum
  • Golgi apparatus
Biofluid Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Basal Ganglia
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Hippocampus
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Stratum Corneum
  • Temporal Lobe
  • Testes
  • Thalamus
Pathways
NameSMPDB LinkKEGG Link
Betaine MetabolismSMP00123map00260
Methionine MetabolismSMP00033map00270
Phospholipid BiosynthesisSMP00025map00564
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified6.0 +/- 0.3 uMAdult (>18 years old)MaleNormal
BloodDetected and Quantified27.5 +/- 3.3 uMNewborn (0-30 days old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified10.6 +/- 1.9 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified6.8 +/- 0.3 uMAdult (>18 years old)FemaleNormal
BloodDetected and Quantified14.5 +/- 5.3 uMAdult (>18 years old)Not SpecifiedNormal
Breast MilkDetected and Quantified116 +/- 22 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified3 +/- 1 uMNot SpecifiedBothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified8.3 (7.0-13.0) uMAdult (>18 years old)BothNormal
  • Geigy Scient...
SalivaDetected and Quantified>10 uMAdult (>18 years old)BothNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal
UrineDetected and Quantified3.5 (1.4-6.1) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified5.27 umol/mmol creatinineAdult (>18 years old)MaleNormal
  • Shaykhutdino...
UrineDetected and Quantified6.3 (0.72-28.5) umol/mmol creatinineChildren (1-13 year old)MaleNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified9.7 +/- 4.5 uMAdult (>18 years old)Not SpecifiedHeart Transplant
Cerebrospinal Fluid (CSF)Detected and Quantified170.0 +/- 70.0 uMAdult (>18 years old)BothSpina bifida
Cerebrospinal Fluid (CSF)Detected and Quantified1.46 +/- 0.54 uMAdult (>18 years old)Not SpecifiedVascular dementia
Cerebrospinal Fluid (CSF)Detected and Quantified140.0 +/- 180.0 uMAdult (>18 years old)BothSpina bifida
Cerebrospinal Fluid (CSF)Detected and Quantified2.5 +/- 1.0 uMElderly (>65 years old)BothAlzheimer's disease
UrineDetected and Quantified3.0 (0.0-8.0) umol/mmol creatinineNot SpecifiedBothLung cancer
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  • 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
Lung Cancer
  • Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. Pubmed: 18953024
Spina Bifida
  • 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
Multi-infarct dementia
  • 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
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000710
KNApSAcK IDC00007298
Chemspider ID299
KEGG Compound IDC00114
BioCyc IDCPD-563
BiGG ID33910
Wikipedia LinkCholine
NuGOwiki LinkHMDB00097
Metagene LinkHMDB00097
METLIN ID56
PubChem Compound305
PDB IDCHT
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)Not Available
General References
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. Zeisel SH: Nutritional importance of choline for brain development. J Am Coll Nutr. 2004 Dec;23(6 Suppl):621S-626S. Pubmed: 15640516
  11. 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
  12. 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
  13. Zeisel SH: Choline: critical role during fetal development and dietary requirements in adults. Annu Rev Nutr. 2006;26:229-50. Pubmed: 16848706
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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

Enzymes

Gene Name:
CHAT
Uniprot ID:
P28329
Reactions
Acetyl-CoA + Choline unknown Coenzyme A + Acetylcholine details
Gene Name:
PLD2
Uniprot ID:
O14939
Reactions
A phosphatidylcholine + Water unknown Choline + a phosphatidatedetails
Phosphatidylcholine + Water unknown Phosphatidate + Cholinedetails
Gene Name:
PLD1
Uniprot ID:
Q13393
Reactions
A phosphatidylcholine + Water unknown Choline + a phosphatidatedetails
Phosphatidylcholine + Water unknown Phosphatidate + Cholinedetails
Gene Name:
CHDH
Uniprot ID:
Q8NE62
Reactions
Choline + acceptor unknown Betaine aldehyde + reduced acceptordetails
Choline + Acceptor unknown Betaine aldehyde + Reduced acceptordetails
Gene Name:
ACHE
Uniprot ID:
P22303
Reactions
Acetylcholine + Water unknown Choline + Acetic aciddetails
Gene Name:
BCHE
Uniprot ID:
P06276
Reactions
An acylcholine + Water unknown Choline + a carboxylatedetails
Gene Name:
CHKB
Uniprot ID:
Q9Y259
Reactions
Adenosine triphosphate + Choline unknown ADP + Phosphorylcholinedetails
Gene Name:
CHKA
Uniprot ID:
P35790
Reactions
Adenosine triphosphate + Choline unknown ADP + Phosphorylcholinedetails
Gene Name:
ADH5
Uniprot ID:
P11766
Gene Name:
ADH1B
Uniprot ID:
P00325
Gene Name:
ADH1A
Uniprot ID:
P07327
Gene Name:
ADH6
Uniprot ID:
P28332
Gene Name:
ADH1C
Uniprot ID:
P00326
Gene Name:
PHOSPHO1
Uniprot ID:
Q8TCT1
Reactions
Phosphorylcholine + Water unknown Choline + Phosphoric aciddetails
Gene Name:
PLD3
Uniprot ID:
Q8IV08
Reactions
A phosphatidylcholine + Water unknown Choline + a phosphatidatedetails
Phosphatidylcholine + Water unknown Phosphatidate + Cholinedetails
Gene Name:
PLD4
Uniprot ID:
Q96BZ4
Reactions
A phosphatidylcholine + Water unknown Choline + a phosphatidatedetails
Phosphatidylcholine + Water unknown Phosphatidate + Cholinedetails
Gene Name:
Not Available
Uniprot ID:
Q59EA4
Gene Name:
PLD6
Uniprot ID:
Q8N2A8
Gene Name:
GPCPD1
Uniprot ID:
Q9NPB8
Reactions
Glycerophosphocholine + Water unknown Choline + Glycerol 3-phosphatedetails

Transporters

Gene Name:
SLC44A1
Uniprot ID:
Q8WWI5
Gene Name:
SLC5A7
Uniprot ID:
Q9GZV3
Gene Name:
SLC22A1
Uniprot ID:
O15245
Gene Name:
SLC44A4
Uniprot ID:
Q53GD3
Gene Name:
SLC44A2
Uniprot ID:
Q8IWA5
Gene Name:
SLC44A3
Uniprot ID:
Q8N4M1