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Record Information
Version	2.0
Creation Date	2012-05-31 13:48:16 -0600
Update Date	2015-06-03 15:53:52 -0600
Secondary Accession Numbers	ECMDB01252
Identification
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)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaab44da8> Close
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.
Kingdom	Organic compounds
Super Class	Organic nitrogen compounds
Class	Organonitrogen compounds
Sub Class	Quaternary ammonium salts
Direct Parent	Tetraalkylammonium salts
Alternative Parents	Organopnictogen compounds Organic salts Organic oxides Hydrocarbon derivatives Amines Aldehydes Organic cations
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 Framework	Aliphatic acyclic compounds
External Descriptors	quaternary ammonium ion (CHEBI:15710 ) a small molecule (BETAINE_ALDEHYDE )
Physical Properties
State:	Solid
Charge:	1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.93 g/L ALOGPS logP -2.7 ALOGPS logP -4.7 ChemAxon logS -2.2 ALOGPS pKa (Strongest Basic) -8.2 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 17.07 Ų ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 41.06 m³·mol⁻¹ ChemAxon Polarizability 11.64 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 sulfur metabolism (ethanesulfonate) PW000925 sulfur metabolism (isethionate) PW000926 sulfur metabolism (methanesulfonate) PW000927 sulfur metabolism (propanesulfonate) PW000924
KEGG Pathways:	Glycine, serine and threonine metabolism ec00260 Metabolic pathways eco01100
EcoCyc Pathways:	glycine betaine biosynthesis I (Gram-negative bacteria) BETSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0pb9-9200000000-421de623448d638559ba View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0pb9-9400000000-f6a6158eae2887c8c1b6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0a4i-9000000000-a88ccc4efc693cee968e View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0udi-1900000000-c0d04b882f6ce11b3cd0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0udi-3900000000-4f77db778fd255f71dd2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0a4i-9100000000-5c1b81d01b1990f7dca0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0a4i-9000000000-692d4006b060a156af58 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 7V, positive splash10-0a4i-9000000000-a0f8f51b132a9c6b49fe View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 4V, positive splash10-0f6x-9400000000-22287f9ceaea3897977a View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 5V, positive splash10-0udl-9700000000-d1b3630f59ab06687bec View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 7V, positive splash10-0udl-9700000000-5daee890b99e88ca3863 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 10V, positive splash10-0zfu-9500000000-ad58eac6d9e695625dfd View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 15V, positive splash10-0a4l-9200000000-cd66506aaa5b99e64441 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 17V, positive splash10-0a4l-9100000000-9d37cb03fd6c5fcec3e6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 20V, positive splash10-0a4i-9000000000-7a7c6e00e7abea9f0814 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 23V, positive splash10-0a4i-9000000000-651a97bfe861cc4973f7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 25V, positive splash10-0a4i-9000000000-59d7cad20ff065ba2f6f View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 27V, positive splash10-0a4i-9000000000-485481563cd89be3d736 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 30V, positive splash10-0a4i-9000000000-c2ada75b19fab2af1a11 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 33V, positive splash10-0a4i-9000000000-9235a6f53edfdaa4de3e View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 35V, positive splash10-0a4i-9000000000-e42443a076dcb59982c9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 40V, positive splash10-0a4i-9000000000-7d7369273ce75b201fbe View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 45V, positive splash10-0a4l-9000000000-2a95a181dc0fc993aaa3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udi-1900000000-b4d3df384d18e299514f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udi-9700000000-1e9685e60dac71951689 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00e9-9000000000-766e4b072c03c25f1477 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
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
Links
External Links:	Resource Link CHEBI ID 15710 HMDB ID HMDB01252 Pubchem Compound ID 249 Kegg ID C00576 ChemSpider ID 244 Wikipedia BTL BioCyc ID BETAINE_ALDEHYDE EcoCyc ID BETAINE_ALDEHYDE Ligand Expo BTL

Enzymes