Record Information
Version2.0
Creation Date2012-05-31 13:48:16 -0600
Update Date2015-06-03 15:53:52 -0600
Secondary Accession Numbers
  • ECMDB01252
Identification
Name:Betaine aldehyde
DescriptionBetaine 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)
Structure
Thumb
Synonyms:
  • (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
Weight:Average: 102.1549
Monoisotopic: 102.091889011
InChI Key:SXKNCCSPZDCRFD-UHFFFAOYSA-N
InChI:InChI=1S/C5H12NO/c1-6(2,3)4-5-7/h5H,4H2,1-3H3/q+1
CAS number:7418-61-3
IUPAC Name:trimethyl(2-oxoethyl)azanium
Traditional IUPAC Name:betaine aldehyde
SMILES:C[N+](C)(C)CC=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentTetraalkylammonium salts
Alternative Parents
Substituents
  • Tetraalkylammonium salt
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Carbonyl group
  • Amine
  • Aldehyde
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.93 g/LALOGPS
logP-2.7ALOGPS
logP-4.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.06 m³·mol⁻¹ChemAxon
Polarizability11.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Choline + NAD > Betaine aldehyde + Hydrogen ion + NADH
Betaine aldehyde + Water + NADP > Betaine +2 Hydrogen ion + NADPH
Betaine aldehyde + Water + NAD <> Betaine +2 Hydrogen ion + NADH
Choline + Acceptor + Acceptor <> Betaine aldehyde + Reduced acceptor + Reduced acceptor
Betaine aldehyde + NADP + Water <> Betaine + NADPH +2 Hydrogen ion
Betaine aldehyde + NAD + Water > Hydrogen ion + Betaine + NADH
Choline + an oxidized electron acceptor > Betaine aldehyde + a reduced electron acceptor
Choline + acceptor > Betaine aldehyde + reduced acceptor
Betaine aldehyde + NAD + Water > Betaine + NADH
alkylsulfonate + FMNH2 + Oxygen > Betaine aldehyde + Sulfite + Flavin Mononucleotide + Water +2 Hydrogen ion + Sulfite
Butanesulfonate + Oxygen + FMNH2 > Hydrogen ion + Water + Sulfite + Flavin Mononucleotide + Betaine aldehyde + Sulfite
Oxygen + FMNH2 + 3-(N-morpholino)propanesulfonate > Sulfite + Water + Hydrogen ion + Flavin Mononucleotide + Betaine aldehyde + Sulfite
ethanesulfonate + Oxygen + FMNH2 > Hydrogen ion + Water + Flavin Mononucleotide + Sulfite + Betaine aldehyde + Sulfite
isethionate + Oxygen + FMNH2 > Betaine aldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite + Sulfite
Oxygen + methanesulfonate + FMNH2 + Methanesulfonate > Hydrogen ion + Water + Flavin Mononucleotide + Sulfite + Betaine aldehyde + Sulfite
Choline + Acceptor <> Betaine aldehyde + Reduced acceptor
Betaine aldehyde + Water + NADP > Betaine +2 Hydrogen ion + NADPH
Choline + Acceptor <> Betaine aldehyde + Reduced acceptor
Betaine aldehyde + Water + NADP > Betaine +2 Hydrogen ion + NADPH
SMPDB Pathways:
sulfur metabolism (butanesulfonate)PW000923 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (ethanesulfonate)PW000925 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (isethionate)PW000926 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (methanesulfonate)PW000927 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (propanesulfonate)PW000924 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • glycine betaine biosynthesis I (Gram-negative bacteria) BETSYN-PWY
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-9200000000-421de623448d638559baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0pb9-9400000000-f6a6158eae2887c8c1b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-a88ccc4efc693cee968eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-1900000000-c0d04b882f6ce11b3cd0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-3900000000-4f77db778fd255f71dd2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9100000000-5c1b81d01b1990f7dca0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-692d4006b060a156af58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-b4d3df384d18e299514fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9700000000-1e9685e60dac71951689View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00e9-9000000000-766e4b072c03c25f1477View in MoNA
References
References:
  • 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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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:
ResourceLink
CHEBI ID15710
HMDB IDHMDB01252
Pubchem Compound ID249
Kegg IDC00576
ChemSpider ID244
WikipediaBTL
BioCyc IDBETAINE_ALDEHYDE
EcoCyc IDBETAINE_ALDEHYDE
Ligand ExpoBTL

Enzymes

General function:
Involved in choline dehydrogenase activity
Specific function:
Can catalyze the oxidation of choline to betaine aldehyde and betaine aldehyde to glycine betaine at the same rate
Gene Name:
betA
Uniprot ID:
P17444
Molecular weight:
61877
Reactions
Choline + acceptor = betaine aldehyde + reduced acceptor.
General function:
Involved in oxidoreductase activity
Specific function:
Betaine aldehyde + NAD(+) + H(2)O = betaine + NADH
Gene Name:
betB
Uniprot ID:
P17445
Molecular weight:
52911
Reactions
Betaine aldehyde + NAD(+) + H(2)O = betaine + NADH.
General function:
Involved in alkanesulfonate monooxygenase activity
Specific function:
Involved in desulfonation of aliphatic sulfonates. Catalyzes the conversion of pentanesulfonic acid to sulfite and pentaldehyde and is able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers
Gene Name:
ssuD
Uniprot ID:
P80645
Molecular weight:
41736
Reactions
An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O.