ECMDB: Betaine aldehyde (ECMDB01252) (M2MDB000309)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (375)

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

MOL SDF PDB SMILES InChI

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

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:

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 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.06 m³·mol⁻¹	ChemAxon
Polarizability	11.64 Å³	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:

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

Protein Details

1. Choline dehydrogenase

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.

Protein Details

2. Betaine aldehyde dehydrogenase

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.

Protein Details

3. Alkanesulfonate monooxygenase

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.

Betaine aldehyde (ECMDB01252) (M2MDB000309)

Structure for #<Compound:0xaaae6460>

Enzymes

Reactions

Reactions

Reactions