Betaine aldehyde (CHEM035139)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:31:15 UTC
Update Date2016-11-09 01:21:15 UTC
Accession NumberCHEM035139
Identification
Common NameBetaine aldehyde
ClassSmall Molecule
DescriptionA quaternary ammonium ion that is nitrogen substituted by three methyl groups and a 2-oxoethyl group. It is an intermediate in the metabolism of amino acids like glycine, serine and threonine.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Glycine betaine aldehydeChEBI
(Formylmethyl)trimethyl-ammoniumHMDB
(Formylmethyl)trimethylammoniumHMDB
BTLHMDB
N,N,N-Trimethyl-2-oxo ethanaminiumHMDB
N,N,N-Trimethyl-2-oxo-ethanaminiumHMDB
Trimethyl(formylmethyl)ammoniumHMDB
Betaine aldehydeHMDB
N,N,N-Trimethyl-2-oxoethanaminiumHMDB
Chemical FormulaC5H12NO
Average Molecular Mass102.155 g/mol
Monoisotopic Mass102.092 g/mol
CAS Registry Number7418-61-3
IUPAC Nametrimethyl(2-oxoethyl)azanium
Traditional Namebetaine aldehyde
SMILESC[N+](C)(C)CC=O
InChI IdentifierInChI=1S/C5H12NO/c1-6(2,3)4-5-7/h5H,4H2,1-3H3/q+1
InChI KeySXKNCCSPZDCRFD-UHFFFAOYSA-N
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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentTetraalkylammonium 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 FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.93 g/LALOGPS
logP-2.7ALOGPS
logP-4.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.06 m³·mol⁻¹ChemAxon
Polarizability11.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-9200000000-421de623448d638559baSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0pb9-9400000000-f6a6158eae2887c8c1b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-a88ccc4efc693cee968eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-1900000000-c0d04b882f6ce11b3cd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-3900000000-4f77db778fd255f71dd2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9100000000-5c1b81d01b1990f7dca0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-692d4006b060a156af58Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 7V, positivesplash10-0a4i-9000000000-a0f8f51b132a9c6b49feSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0f6x-9400000000-22287f9ceaea3897977aSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0udl-9700000000-d1b3630f59ab06687becSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0udl-9700000000-5daee890b99e88ca3863Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0zfu-9500000000-ad58eac6d9e695625dfdSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-0a4l-9200000000-cd66506aaa5b99e64441Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-0a4l-9100000000-9d37cb03fd6c5fcec3e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-0a4i-9000000000-7a7c6e00e7abea9f0814Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-0a4i-9000000000-651a97bfe861cc4973f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-0a4i-9000000000-59d7cad20ff065ba2f6fSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0a4i-9000000000-485481563cd89be3d736Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0a4i-9000000000-c2ada75b19fab2af1a11Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0a4i-9000000000-9235a6f53edfdaa4de3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0a4i-9000000000-e42443a076dcb59982c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0a4i-9000000000-7d7369273ce75b201fbeSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0a4l-9000000000-2a95a181dc0fc993aaa3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-b4d3df384d18e299514fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9700000000-1e9685e60dac71951689Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00e9-9000000000-766e4b072c03c25f1477Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04401
HMDB IDHMDB0001252
FooDB IDFDB022513
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID35400
BioCyc IDBETAINE_ALDEHYDE
METLIN ID278
PDB IDNot Available
Wikipedia LinkBetaine_aldehyde
Chemspider ID244
ChEBI ID15710
PubChem Compound ID249
Kegg Compound IDC00576
YMDB IDNot Available
ECMDB IDECMDB01252
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22569963
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23563483
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23823928
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24747910
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. Yilmaz JL, Bulow L: Enhanced stress tolerance in Escherichia coli and Nicotiana tabacum expressing a betaine aldehyde dehydrogenase/choline dehydrogenase fusion protein. Biotechnol Prog. 2002 Nov-Dec;18(6):1176-82.
14. 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.