Betaine (PAMDB000564)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000564
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 Pseudomonas aeruginosa and increases the growth rate of osmotically stressed Pseudomonas aeruginosa.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 118.1543
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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).
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Alpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Quaternary ammonium salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular Framework Aliphatic 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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.99 m3·mol-1ChemAxon
Polarizability12.52 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + Water + Betaine > ADP + Betaine + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Betaine > ADP + Betaine + Hydrogen ion + Phosphate
Betaine aldehyde + Water + NADP > Betaine +2 Hydrogen ion + NADPH
Betaine aldehyde + Water + NAD <> Betaine +2 Hydrogen ion + NADH
Betaine aldehyde + NAD + Water > Betaine + NADH
Pathways:
Spectra
Spectra:
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

Protein Details
• Betaine aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Betaine aldehyde + NAD(+) + H(2)O = betaine + NADH
Gene Name:
betB
Locus Tag:
PA5373
Molecular weight:
53.3 kDa
Reactions
Betaine aldehyde + NAD(+) + H(2)O = betaine + NADH.

Transporters