| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:07:48 -0700 |
| HMDB ID |
HMDB00043 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Betaine |
| Description |
Betaine or trimethylglycine is a methylated derivative of glycine. It functions as a methyl donor in that it carries and donates methyl functional groups to facilitate necessary chemical processes. The donation of methyl groups is important to proper liver function, cellular replication, and detoxification reactions. Betaine also plays a role in the manufacture of carnitine and serves to protect the kidneys from damage. Betaine has also been of interest for its role in osmoregulation. As a drug, betaine hydrochloride has been used as a source of hydrochloric acid in the treatment of hypochlorhydria. Betaine has also been used in the treatment of liver disorders, for hyperkalemia, for homocystinuria, and for gastrointestinal disturbances. (From Martindale, The Extra Pharmacopoeia, 30th Ed, p1341). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (Carboxymethyl)trimethylammonium hydroxide inner salt
- (Trimethylammonio)acetate
- 1-Carboxy-N,N,N-trimethyl-Methanaminium
- 1-Carboxy-N,N,N-trimethyl-Methanaminium hydroxide
- 1-Carboxy-N,N,N-trimethylmethanaminium inner salt
- a-Earleine
- Abromine
- alpha-Earleine
- Aminocoat
- Betafin
- Betafin BCR
- Betafin BP
- Betaine
- Cystadane
- Ektasolve EE
- FinnStim
- Glycine betaine
- Glycocoll betaine
- Glycylbetaine
- Greenstim
- Loramine AMB 13
- Loramine AMB-13
- Lycine
- N,N,N-Trimethylglycine
- Oxyneurine
- Rubrine C
- Trimethylaminoacetate
- Trimethylaminoacetic acid
- Trimethylbetaine Glycine
- Trimethylglycine
- Trimethylglycocoll
|
| Chemical Formula |
C5H11NO2 |
| Average Molecular Weight |
117.1463 |
| Monoisotopic Molecular Weight |
117.078978601 |
| IUPAC Name |
2-(trimethylazaniumyl)acetate |
| Traditional IUPAC Name |
betaine |
| CAS Registry Number |
107-43-7 |
| SMILES |
C[N+](C)(C)CC([O-])=O |
| InChI Identifier |
InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 |
| InChI Key |
KWIUHFFTVRNATP-UHFFFAOYSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Amino Acids, Peptides, and Analogues |
| Class |
Amino Acids and Derivatives |
| Sub Class |
Alpha Amino Acids and Derivatives |
| Other Descriptors |
- Aliphatic Acyclic Compounds
- a methylated methyl acceptor(Cyc)
- amino-acid betaine(ChEBI)
- glycine derivative(ChEBI)
|
| Substituents |
- Carboxylic Acid Salt
- Quaternary Ammonium Salt
|
| Direct Parent |
Alpha Amino Acids and Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Glycine, serine and threonine metabolism
- Component of Methionine metabolism
- Osmolyte
|
| Application |
Not Available |
| Cellular locations |
- Cytoplasm
- Extracellular
- Mitochondria
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
293 - 301 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
611.0 mg/mL at 19 °C |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|
|
| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Extracellular
- Mitochondria
|
| Biofluid Locations |
|
| Tissue Location |
- Skeletal Muscle
- Bladder
- Fibroblasts
- Intestine
- Pancreas
- Placenta
- Testes
- Kidney
- Liver
- Prostate
- Adrenal Gland
- Skin
- Adipose Tissue
- Adrenal Cortex
- Platelet
- Gonads
- Gut
- Spleen
- Stratum Corneum
|
| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
33.6 (23.9-42.1) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
82.0 (20.0-144.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
72 +/- 22.4 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
18.6 (4.868-32.4) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
11.5 (2.7-24.7) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
urine by NMR
|
| Urine |
Detected and Quantified |
|
4.14 umol/mmol creatinine |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Male |
Normal |
After green tea sonsumption
|
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Male |
Normal |
After black tea sonsumption
|
| Urine |
Detected and Quantified |
|
6.1 +/- 3.2 umol/mmol creatinine |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
49.6 (6.4-92.7) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
42.1 +/- 19.3 uM |
Adult (>18 years old) |
Not Specified |
Heart Transplant |
Not Available |
| Blood |
Detected and Quantified |
|
32.5 (23.9-42.5) uM |
Adult (>18 years old) |
Both |
Chronic renal failure |
Not Available |
| Blood |
Detected and Quantified |
|
25.6 (23.4-36.6) uM |
Adult (>18 years old) |
Both |
Continuous ambulatory peritoneal dialysis |
Not Available |
| Blood |
Detected and Quantified |
|
31.9 (28.3-36.2) uM |
Adult (>18 years old) |
Both |
Hemodialysis |
Not Available |
| Urine |
Detected and Quantified |
|
6.0 (0.0-16.0) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Lung cancer |
Not Available |
| Urine |
Detected and Quantified |
|
51.2 +/- 7.6 umol/mmol creatinine |
Adult (>18 years old) |
Both |
3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency |
Not Available |
| Urine |
Detected and Quantified |
|
76.2 +/- 8 umol/mmol creatinine |
Adult (>18 years old) |
Both |
3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency |
Not Available |
| Urine |
Detected and Quantified |
|
210.1 +/- 16.4 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Arginosuccinic aciduria |
Not Available |
| Urine |
Detected and Quantified |
|
20.1 +/- 4.7 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Propionic acidemia |
Not Available |
| Urine |
Detected and Quantified |
|
122 +/- 13.6 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Propionic acidemia |
Not Available |
| Urine |
Detected and Quantified |
|
8.5 +/- 0.4 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Phenylketonuria |
Not Available |
| Urine |
Detected and Quantified |
|
14.3 +/- 2.7 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Phenylketonuria |
Not Available |
| Urine |
Detected and Quantified |
|
14.2 +/- 0.9 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Maple syrup urine disease |
Not Available |
| Urine |
Detected and Quantified |
|
58 +/- 2.2 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Aminoaciduria |
Not Available |
|
| Associated Disorders and Diseases |
| Disease References |
| Lung Cancer |
|
|
| Chronic renal failure |
- McGregor DO, Dellow WJ, Lever M, George PM, Robson RA, Chambers ST: Dimethylglycine accumulates in uremia and predicts elevated plasma homocysteine concentrations. Kidney Int. 2001 Jun;59(6):2267-72.
Pubmed: 11380830
|
| Continuous ambulatory peritoneal dialysis |
- McGregor DO, Dellow WJ, Lever M, George PM, Robson RA, Chambers ST: Dimethylglycine accumulates in uremia and predicts elevated plasma homocysteine concentrations. Kidney Int. 2001 Jun;59(6):2267-72.
Pubmed: 11380830
|
| Hemodialysis |
- McGregor DO, Dellow WJ, Lever M, George PM, Robson RA, Chambers ST: Dimethylglycine accumulates in uremia and predicts elevated plasma homocysteine concentrations. Kidney Int. 2001 Jun;59(6):2267-72.
Pubmed: 11380830
|
|
| Associated OMIM IDs |
|
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB009020 |
| KNApSAcK ID |
C00007291  |
| Chemspider ID |
242  |
| KEGG Compound ID |
C00719  |
| BioCyc ID |
BETAINE  |
| BiGG ID |
35786  |
| Wikipedia Link |
Betaine  |
| NuGOwiki Link |
HMDB00043  |
| Metagene Link |
HMDB00043  |
| METLIN ID |
287  |
| PubChem Compound |
247  |
| PDB ID |
Not Available |
| ChEBI ID |
17750  |
| References |
| Synthesis Reference |
Mu, Yun; Guo, Xiao-hui. Improved process for preparation of betaine. Huaxue Yu Shengwu Gongcheng (2005), 22(7), 48-49. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Surtees R, Bowron A, Leonard J: Cerebrospinal fluid and plasma total homocysteine and related metabolites in children with cystathionine beta-synthase deficiency: the effect of treatment. Pediatr Res. 1997 Nov;42(5):577-82.
Pubmed: 9357926
- Holm PI, Ueland PM, Kvalheim G, Lien EA: Determination of choline, betaine, and dimethylglycine in plasma by a high-throughput method based on normal-phase chromatography-tandem mass spectrometry. Clin Chem. 2003 Feb;49(2):286-94.
Pubmed: 12560353
- Knopman D, Patterson M: An open-label, 24-week pilot study of the methyl donor betaine in Alzheimer disease patients. Alzheimer Dis Assoc Disord. 2001 Jul-Sep;15(3):162-5.
Pubmed: 11522934
- Schwahn BC, Chen Z, Laryea MD, Wendel U, Lussier-Cacan S, Genest J Jr, Mar MH, Zeisel SH, Castro C, Garrow T, Rozen R: Homocysteine-betaine interactions in a murine model of 5,10-methylenetetrahydrofolate reductase deficiency. FASEB J. 2003 Mar;17(3):512-4. Epub 2003 Jan 22.
Pubmed: 12551843
- Abdelmalek MF, Angulo P, Jorgensen RA, Sylvestre PB, Lindor KD: Betaine, a promising new agent for patients with nonalcoholic steatohepatitis: results of a pilot study. Am J Gastroenterol. 2001 Sep;96(9):2711-7.
Pubmed: 11569700
- Abu Al-Soud W, Radstrom P: Effects of amplification facilitators on diagnostic PCR in the presence of blood, feces, and meat. J Clin Microbiol. 2000 Dec;38(12):4463-70.
Pubmed: 11101581
- Sakamoto A, Ono H, Mizoguchi N, Sakura N: Betaine and homocysteine concentrations in infant formulae and breast milk. Pediatr Int. 2001 Dec;43(6):637-40.
Pubmed: 11737741
- Schwab U, Torronen A, Toppinen L, Alfthan G, Saarinen M, Aro A, Uusitupa M: Betaine supplementation decreases plasma homocysteine concentrations but does not affect body weight, body composition, or resting energy expenditure in human subjects. Am J Clin Nutr. 2002 Nov;76(5):961-7.
Pubmed: 12399266
- Chambers ST, Kunin CM: Isolation of glycine betaine and proline betaine from human urine. Assessment of their role as osmoprotective agents for bacteria and the kidney. J Clin Invest. 1987 Mar;79(3):731-7.
Pubmed: 3546377
- Laryea MD, Steinhagen F, Pawliczek S, Wendel U: Simple method for the routine determination of betaine and N,N-dimethylglycine in blood and urine. Clin Chem. 1998 Sep;44(9):1937-41.
Pubmed: 9732980
- Chung YL, Rider LG, Bell JD, Summers RM, Zemel LS, Rennebohm RM, Passo MH, Hicks J, Miller FW, Scott DL: Muscle metabolites, detected in urine by proton spectroscopy, correlate with disease damage in juvenile idiopathic inflammatory myopathies. Arthritis Rheum. 2005 Aug 15;53(4):565-70.
Pubmed: 16082628
- Go EK, Jung KJ, Kim JY, Yu BP, Chung HY: Betaine suppresses proinflammatory signaling during aging: the involvement of nuclear factor-kappaB via nuclear factor-inducing kinase/IkappaB kinase and mitogen-activated protein kinases. J Gerontol A Biol Sci Med Sci. 2005 Oct;60(10):1252-64.
Pubmed: 16282556
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.
Pubmed: 19212411
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