P. aeruginosa Metabolome Database: Betaine aldehyde (PAMDB000309)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000309

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 View Structure

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

Average Molecular Weight:

102.1549

Monoisotopic Molecular Weight:

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

Taxonomy Description

This 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 Class

Organonitrogen compounds

Class

Quaternary ammonium salts

Sub Class

Not Available

Direct Parent

Quaternary ammonium salts

Alternative Parents

Substituents

Quaternary ammonium salt
Hydrocarbon derivative
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	0.932 mg/mL	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:

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
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

Pathways:

Glycine, serine and threonine metabolism pae00260
Metabolic pathways pae01100

Spectra

Spectra:

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

Betaine aldehyde (PAMDB000309)

Structure for Betaine aldehyde (PAMDB000309)