| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:07:53 -0700 |
| HMDB ID |
HMDB00097 |
| 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 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (2-Hydroxyethyl)trimethyl ammonium
- (2-Hydroxyethyl)trimethylammonium
- (beta-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 |
| Average Molecular Weight |
104.1708 |
| Monoisotopic Molecular Weight |
104.107539075 |
| IUPAC Name |
(2-hydroxyethyl)trimethylazanium |
| Traditional IUPAC 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 |
| Kingdom |
Organic Compounds |
| Super Class |
Aliphatic Acyclic Compounds |
| Class |
Alcohols and Polyols |
| Sub Class |
Cholines |
| Other Descriptors |
- Pesticides(KEGG)
- a small molecule(Cyc)
- cholines(ChEBI)
|
| Substituents |
- Primary Alcohol
- Quaternary Ammonium Salt
|
| Direct Parent |
Cholines |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Glycerophospholipid metabolism
- Component of Glycine, serine and threonine metabolism
- Component of Glycosphingolipid metabolism
- Essential vitamins
|
| Application |
Not Available |
| Cellular locations |
- Cytoplasm
- Extracellular
- Mitochondria
- Nucleus
- Endoplasmic reticulum
- Golgi apparatus
|
| 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 |
|
| 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 |
- Muscle
- Skeletal Muscle
- Bladder
- Fibroblasts
- Intestine
- Neuron
- Placenta
- Testes
- Kidney
- Liver
- Epidermis
- Brain
- Myelin
- Prostate
- Nerve Cells
- Platelet
- Spleen
- Stratum Corneum
- Basal Ganglia
- Hippocampus
- Temporal Lobe
- Thalamus
|
| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
6.0 +/- 0.3 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
27.5 +/- 3.3 uM |
Newborn (0-30 days old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
10.6 +/- 1.9 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
6.8 +/- 0.3 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
14.5 +/- 5.3 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Breast Milk |
Detected and Quantified |
|
116 +/- 22 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
3 +/- 1 uM |
Not Specified |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
8.3 (7.0-13.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Saliva |
Detected and Quantified |
|
>10 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
3.5 (1.4-6.1) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
urine by NMR
|
| Urine |
Detected and Quantified |
|
5.27 umol/mmol creatinine |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
6.3 (0.72-28.5) umol/mmol creatinine |
Children (1-13 year old) |
Male |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
9.7 +/- 4.5 uM |
Adult (>18 years old) |
Not Specified |
Heart Transplant |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
170.0 +/- 70.0 uM |
Adult (>18 years old) |
Both |
Spina bifida |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
1.46 +/- 0.54 uM |
Adult (>18 years old) |
Not Specified |
Vascular dementia |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
140.0 +/- 180.0 uM |
Adult (>18 years old) |
Both |
Spina bifida |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
2.5 +/- 1.0 uM |
Elderly (>65 years old) |
Both |
Alzheimer's disease |
Not Available |
| Urine |
Detected and Quantified |
|
3.0 (0.0-8.0) umol/mmol creatinine |
Not Specified |
Both |
Lung cancer |
Not Available |
|
| Associated Disorders and Diseases |
| Disease References |
| 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
|
| Lung Cancer |
|
|
| 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
|
| 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
|
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| Associated OMIM IDs |
|
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB000710 |
| KNApSAcK ID |
C00007298  |
| Chemspider ID |
299  |
| KEGG Compound ID |
C00114  |
| BioCyc ID |
CPD-563  |
| BiGG ID |
33910  |
| Wikipedia Link |
Choline  |
| NuGOwiki Link |
HMDB00097  |
| Metagene Link |
HMDB00097  |
| METLIN ID |
56  |
| PubChem Compound |
305  |
| PDB ID |
CHT  |
| 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 |
- 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
- 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
- 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
- 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
- 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
- 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: Nutritional importance of choline for brain development. J Am Coll Nutr. 2004 Dec;23(6 Suppl):621S-626S.
Pubmed: 15640516
- 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
- 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
- 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
- Zeisel SH: Choline: critical role during fetal development and dietary requirements in adults. Annu Rev Nutr. 2006;26:229-50.
Pubmed: 16848706
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
|
| Enzymes |
|
|
| Name: |
Phospholipase D2
|
| Reactions: |
- a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
|
| Gene Name: |
PLD2 |
| Uniprot ID: |
O14939  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Phospholipase D1
|
| Reactions: |
- a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
|
| Gene Name: |
PLD1 |
| Uniprot ID: |
Q13393  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
| Name: |
Cholinesterase
|
| Reactions: |
- an acylcholine + H2O = choline + a carboxylate [RN:R01029]
|
| Gene Name: |
BCHE |
| Uniprot ID: |
P06276  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
| Name: |
Phospholipase D3
|
| Reactions: |
- a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
|
| Gene Name: |
PLD3 |
| Uniprot ID: |
Q8IV08  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Phospholipase D4
|
| Reactions: |
- a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
|
| Gene Name: |
PLD4 |
| Uniprot ID: |
Q96BZ4  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
| Name: |
Phospholipase D6
|
| Reactions: |
- a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
|
| Gene Name: |
PLD6 |
| Uniprot ID: |
Q8N2A8  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|