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Bovine Metabolome Database



Showing metabocard for Betaine (BMDB00043)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-28 10:24:19
Accession Number BMDB00043
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)
Synonyms
  1. (Carboxymethyl)trimethylammonium hydroxide inner salt
  2. (Trimethylammonio)acetate
  3. 1-Carboxy-N,N,N-trimethylmethanaminium inner salt
  4. 1-carboxy-N,N,N-trimethyl-Methanaminium
  5. 1-carboxy-N,N,N-trimethyl-Methanaminium hydroxide
  6. Abromine
  7. Aminocoat
  8. Betafin
  9. Betafin BCR
  10. Betafin BP
  11. Betaine
  12. Cystadane
  13. Ektasolve EE
  14. FinnStim
  15. Glycine betaine
  16. Glycocoll betaine
  17. Glycylbetaine
  18. Greenstim
  19. Loramine AMB 13
  20. Loramine AMB-13
  21. Lycine
  22. N,N,N-Trimethylglycine
  23. Oxyneurine
  24. Rubrine C
  25. Trimethylaminoacetate
  26. Trimethylaminoacetic acid
  27. Trimethylglycine
  28. Trimethylglycocoll
  29. a-Earleine
  30. alpha-Earleine
  31. trimethylbetaine Glycine
Chemical IUPAC Name 2-trimethylammonioacetate
Chemical Formula C5H11NO2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Quaternary Amines; Amino Acids
Sub Class
  • Short chain quaternary ammonium salts
Family
  • Mammalian_Metabolite
Species
  • cation; anion; quaternary ammonium salt; carboxylic acid salt
Biofunction
  • Osmolyte; Component of Glycine, serine and threonine metabolism; Component of Methionine metabolism
Application
Source
  • Endogenous
Average Molecular Weight 117.146
Monoisotopic Molecular Weight 117.078979
Isomeric SMILES C[N+](C)(C)CC([O-])=O
Canonical SMILES C[N+](C)(C)CC([O-])=O
KEGG Compound ID C00719 Link Image
BioCyc ID BETAINE Link Image
BiGG ID 35786 Link Image
Wikipedia Link Betaine Link Image
METLIN ID 287 Link Image
PubChem Compound 247 Link Image
PubChem Substance 2165 Link Image
ChEBI ID 17750 Link Image
CAS Registry Number 107-43-7
InChI Identifier InChI=1/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
Synthesis Reference Mu, Yun; Guo, Xiao-hui. Improved process for preparation of betaine. Huaxue Yu Shengwu Gongcheng (2005), 22(7), 48-49.
Melting Point (Experimental) 293 oC ( Soicke, H., Fitoterapia 1988, V59(1), P73-5); 301 oC dec.
Experimental Water Solubility 611.0 mg/mL at 19 oC [YALKOWSKY,SH & DANENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 1.86 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.70 [Predicted by ALOGPS]; -4.93 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Download Spectrum
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Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Show Image
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Cellular Location
  • Cytoplasm
  • Extracellular
  • mitochondria
Biofluid Location
  • Breast_Milk
Tissue Location
Tissue References
Adipose Tissue
Adrenal Cortex
Adrenal Gland
Bladder
Epidermis
Fibroblasts
Gonads
Gut
Intestine
Kidney
Liver
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle
Skin
Spleen
Stratum Corneum
Testes
Concentrations (Normal)
Biofluid Breast_Milk
Value 459 - 1410 uM
Age N/A
Sex N/A
Condition Normal
Comments Raw. skim.
References
Biofluid Breast_Milk
Value 597 +/- 44 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in 2% milk
References
Biofluid Breast_Milk
Value 610 +/- 52 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in skim milk
References
Biofluid Breast_Milk
Value 572 +/- 18 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in 1% milk
References
Biofluid Breast_Milk
Value 631 +/- 57 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in 3.25% milk
References
Concentrations (Abnormal) Not Available
Pathway Names
  • Glycine, Serine and Threonine Metabolism
HMDB Pathways
Name Glycine, Serine and Threonine Metabolism
Image Show Link Image
KEGG Pathways
Name Glycine, Serine and Threonine Metabolism
Image Show Link Image
SimCell Pathways
Name Glycine, Serine and Threonine Metabolism
Image Show Link Image
Graph Show Link Image
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General References
  1. Wikipedia Link Image