Record Information
Version2.0
Creation Date2012-05-31 14:02:31 -0600
Update Date2015-10-15 16:14:21 -0600
Secondary Accession Numbers
  • ECMDB04024
Identification
Name:Betaine
Description:Betaine or trimethylglycine is a methylated derivative of glycine. It functions as a methyl donor in that it carries and donates methyl functional groups to facilitate necessary chemical processes. Betaine is an osmoprotectant compound. The accumulation of betaine increases the volume of cytoplasmic water of E. coli and increases the growth rate of osmotically stressed E. coli. (PMID: 1537801)
Structure
Thumb
Synonyms:
  • (Carboxymethyl)trimethylammonium hydroxide inner salt
  • (Trimethylammonio)acetate
  • (Trimethylammonio)acetic acid
  • 1-Carboxy-N,N,N-trimethyl-Methanaminium
  • 1-Carboxy-N,N,N-trimethyl-Methanaminium hydroxide
  • 1-Carboxy-N,N,N-trimethylmethanaminium inner salt
  • N,N,N-trimethylglycine
  • A-Earleine
  • Abromine
  • Acidin-pepsin
  • Alpha-Earleine
  • Aminocoat
  • Betafin
  • Betafin BCR
  • Betafin BP
  • Betaine
  • Cystadane
  • Ektasolve EE
  • FinnStim
  • Glycine betaine
  • Glycocoll betaine
  • Glycylbetaine
  • Greenstim
  • Loramine AMB 13
  • Loramine AMB-13
  • Lycine
  • N,N,N-Trimethylglycine
  • Oxyneurine
  • Rubrine C
  • Trimethylaminoacetate
  • Trimethylaminoacetic acid
  • Trimethylammonioacetate
  • Trimethylammonioacetic acid
  • Trimethylbetaine Glycine
  • Trimethylglycine
  • Trimethylglycocoll
  • α-Earleine
Chemical Formula:C5H12NO2
Weight:Average: 118.1543
Monoisotopic: 118.086803633
InChI Key:KWIUHFFTVRNATP-UHFFFAOYSA-O
InChI:InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3/p+1
CAS number:107-43-7
IUPAC Name:(carboxymethyl)trimethylazanium
Traditional IUPAC Name:trimethyl glycine
SMILES:C[N+](C)(C)CC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:293 °C ( Soicke, H., Fitoterapia 1988, V59(1), P73-5); 301 oC dec.
Experimental Properties:
PropertyValueSource
Water Solubility:611.0 mg/mL at 19 oC [YALKOWSKY,SH & DANENFELSER,RM (1992)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.75 g/LALOGPS
logP-2.1ALOGPS
logP-4.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.99 m³·mol⁻¹ChemAxon
Polarizability12.52 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Quorum SensingPW000836 ThumbThumb?image type=greyscaleThumb?image type=simple
S-adenosyl-L-methionine cyclePW002080 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, Positivesplash10-0a4l-9300000000-80cfd7f79f6513ad343dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9400000000-bcbb10100105e3e315ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1900000000-047aac93a67d6af67e64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-6900000000-355a370c7a45c53e0d70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9100000000-7a2182a46701caa71a50View in MoNA
References
References:
  • Cayley, S., Lewis, B. A., Record, M. T. Jr (1992). "Origins of the osmoprotective properties of betaine and proline in Escherichia coli K-12." J Bacteriol 174:1586-1595. Pubmed: 1537801
  • 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
  • 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
  • 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
Synthesis Reference:Mu, Yun; Guo, Xiao-hui. Improved process for preparation of betaine. Huaxue Yu Shengwu Gongcheng (2005), 22(7), 48-49.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17750
HMDB IDHMDB00043
Pubchem Compound ID247
Kegg IDC00719
ChemSpider ID242
WikipediaBetaine
BioCyc IDBETAINE
EcoCyc IDBETAINE
Ligand ExpoBET

Enzymes

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 transporter activity
Specific function:
Involved in a multicomponent binding-protein-dependent transport system for glycine betaine/L-proline
Gene Name:
proW
Uniprot ID:
P14176
Molecular weight:
37619
General function:
Involved in transporter activity
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
yehW
Uniprot ID:
P33359
Molecular weight:
25514
General function:
Involved in transporter activity
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
yehY
Uniprot ID:
P33361
Molecular weight:
41138
General function:
Involved in nucleotide binding
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for energy coupling to the transport system
Gene Name:
yehX
Uniprot ID:
P33360
Molecular weight:
34424
General function:
Involved in transporter activity
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules
Gene Name:
osmF
Uniprot ID:
P33362
Molecular weight:
32609

Transporters

General function:
Involved in transporter activity
Specific function:
Probable transporter whose substrate is unknown. Is not involved in aerobic D-malate transport
Gene Name:
yeaV
Uniprot ID:
P0ABD1
Molecular weight:
52881
General function:
Involved in transporter activity
Specific function:
Proton symporter that senses osmotic shifts and responds by importing osmolytes such as proline, glycine betaine, stachydrine, pipecolic acid, ectoine and taurine. It is both an osmosensor and an osmoregulator which is available to participate early in the bacterial osmoregulatory response
Gene Name:
proP
Uniprot ID:
P0C0L7
Molecular weight:
54845
General function:
Involved in transporter activity
Specific function:
Involved in a multicomponent binding-protein-dependent transport system for glycine betaine/L-proline
Gene Name:
proW
Uniprot ID:
P14176
Molecular weight:
37619
General function:
Involved in transporter activity
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
yehW
Uniprot ID:
P33359
Molecular weight:
25514
General function:
Involved in transporter activity
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
yehY
Uniprot ID:
P33361
Molecular weight:
41138
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in nucleotide binding
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for energy coupling to the transport system
Gene Name:
yehX
Uniprot ID:
P33360
Molecular weight:
34424
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules
Gene Name:
osmF
Uniprot ID:
P33362
Molecular weight:
32609
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368