Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000309
Name: Betaine aldehyde
Description:Betaine aldehyde is an intermediate in the metabolism of glycine, serine and threonine. Betaine aldehyde dehydrogenase facilitates the conversion of betaine aldehyde to betaine. (PMID: 12467448, 7646513)
  • (formylmethyl)trimethyl-Ammonium
  • (Formylmethyl)trimethylammonium
  • N,N,N-trimethyl-2-oxoethylammonium
  • Betaine aldehyde
  • BTL
  • Glycine betaine aldehyde
  • N,N,N-Trimethyl-2-oxo Ethanaminium
  • N,N,N-Trimethyl-2-oxo-Ethanaminium
  • N,N,N-Trimethyl-2-oxoethylammonium
  • Trimethyl(formylmethyl)ammonium
Chemical Formula: C5H12NO
Average Molecular Weight: 102.1549
Monoisotopic Molecular Weight: 102.091889011
CAS number: 7418-61-3
IUPAC Name:trimethyl(2-oxoethyl)azanium
Traditional IUPAC Name: betaine aldehyde
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as quaternary ammonium salts. These are compounds containing positively charged polyatomic ion of the structure NR4+, R being an alkyl group or an aryl group.
Kingdom Organic compounds
Super ClassOrganonitrogen compounds
Class Quaternary ammonium salts
Sub ClassNot Available
Direct Parent Quaternary ammonium salts
Alternative Parents
  • Quaternary ammonium salt
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Amine
  • Aldehyde
  • Organic cation
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Melting point: Not Available
Experimental Properties:
Predicted Properties
Water Solubility0.932 mg/mLALOGPS
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.06 m3·mol-1ChemAxon
Polarizability11.64 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
  • Chern MK, Pietruszko R: Human aldehyde dehydrogenase E3 isozyme is a betaine aldehyde dehydrogenase. Biochem Biophys Res Commun. 1995 Aug 15;213(2):561-8. Pubmed: 7646513
  • Chesnoy S, Durand D, Doucet J, Couarraze G: Structural parameters involved in the permeation of propranolol HCl by iontophoresis and enhancers. J Control Release. 1999 Mar 29;58(2):163-75. Pubmed: 10053189
  • Desfosses B, Cittanova N, Urbach W, Waks M: Ligand binding at membrane mimetic interfaces. Human serum albumin in reverse micelles. Eur J Biochem. 1991 Jul 1;199(1):79-87. Pubmed: 1712302
  • 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
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  • Nalecz KA, Miecz D, Berezowski V, Cecchelli R: Carnitine: transport and physiological functions in the brain. Mol Aspects Med. 2004 Oct-Dec;25(5-6):551-67. Pubmed: 15363641
  • Peterson CG, Eklund E, Taha Y, Raab Y, Carlson M: A new method for the quantification of neutrophil and eosinophil cationic proteins in feces: establishment of normal levels and clinical application in patients with inflammatory bowel disease. Am J Gastroenterol. 2002 Jul;97(7):1755-62. Pubmed: 12135031
  • Prester L, Simeon V: Kinetics of the inhibition of human serum cholinesterase phenotypes with the dimethylcarbamate of (2-hydroxy-5-phenylbenzyl)-trimethylammonium bromide (Ro 02-0683). Biochem Pharmacol. 1991 Nov 27;42(12):2313-6. Pubmed: 1764116
  • Scott JE, Newton DJ: The recovery and characterization of acid glycosaminoglycans in normal human urine. Influence of a circadian rhythm. Connect Tissue Res. 1975;3(2):157-64. Pubmed: 126843
  • 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
  • Wang L, Dean DA, Macdonald RC: Effect of vinblastine on transfection: influence of cell types, cationic lipids and promoters. Curr Drug Deliv. 2005 Jan;2(1):93-6. Pubmed: 16305411
  • 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
  • Yilmaz, J. L., Bulow, L. (2002). "Enhanced stress tolerance in Escherichia coli and Nicotiana tabacum expressing a betaine aldehyde dehydrogenase/choline dehydrogenase fusion protein." Biotechnol Prog 18:1176-1182. Pubmed: 12467448
Synthesis Reference: Cromwell, B. T.; Rennie, S. D. Biosynthesis and metabolism of betaines in plants. II. Biosynthesis of glycinebetaine(betaine) in higher plants. Biochemical Journal (1954), 58 318-22.
Material Safety Data Sheet (MSDS) Not Available
External Links:
Pubchem Compound ID249
Kegg IDC00576
ChemSpider ID244
Ligand ExpoBTL