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Record Information
Version1.0
Creation Date2016-09-30 22:43:05 UTC
Update Date2020-05-21 16:28:30 UTC
BMDB IDBMDB0001252
Secondary Accession Numbers
  • BMDB01252
Metabolite Identification
Common NameBetaine aldehyde
DescriptionBetaine aldehyde, also known as BTL, belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains. Betaine aldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Betaine aldehyde exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
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 Weight102.1549
Monoisotopic Molecular Weight102.091889011
IUPAC Nametrimethyl(2-oxoethyl)azanium
Traditional Namebetaine aldehyde
CAS Registry Number7418-61-3
SMILES
C[N+](C)(C)CC=O
InChI Identifier
InChI=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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-9200000000-421de623448d638559baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0pb9-9400000000-f6a6158eae2887c8c1b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-a88ccc4efc693cee968eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-1900000000-c0d04b882f6ce11b3cd0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-3900000000-4f77db778fd255f71dd2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9100000000-5c1b81d01b1990f7dca0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-692d4006b060a156af58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 7V, positivesplash10-0a4i-9000000000-a0f8f51b132a9c6b49feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0f6x-9400000000-22287f9ceaea3897977aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0udl-9700000000-d1b3630f59ab06687becView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0udl-9700000000-5daee890b99e88ca3863View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0zfu-9500000000-ad58eac6d9e695625dfdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-0a4l-9200000000-cd66506aaa5b99e64441View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-0a4l-9100000000-9d37cb03fd6c5fcec3e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-0a4i-9000000000-7a7c6e00e7abea9f0814View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-0a4i-9000000000-651a97bfe861cc4973f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-0a4i-9000000000-59d7cad20ff065ba2f6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0a4i-9000000000-485481563cd89be3d736View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0a4i-9000000000-c2ada75b19fab2af1a11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0a4i-9000000000-9235a6f53edfdaa4de3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0a4i-9000000000-e42443a076dcb59982c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0a4i-9000000000-7d7369273ce75b201fbeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0a4l-9000000000-2a95a181dc0fc993aaa3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-b4d3df384d18e299514fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9700000000-1e9685e60dac71951689View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00e9-9000000000-766e4b072c03c25f1477View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Epidermis
  • Kidney
  • Neuron
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001252
DrugBank IDDB04401
Phenol Explorer Compound IDNot Available
FooDB IDFDB022513
KNApSAcK IDNot Available
Chemspider ID244
KEGG Compound IDC00576
BioCyc IDBETAINE_ALDEHYDE
BiGG ID35400
Wikipedia LinkBetaine_aldehyde
METLIN ID278
PubChem Compound249
PDB IDNot Available
ChEBI ID15710
References
Synthesis ReferenceCromwell, 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
General ReferencesNot Available

Enzymes

General function:
Energy production and conversion
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism (By similarity).
Gene Name:
ALDH7A1
Uniprot ID:
Q2KJC9
Molecular weight:
58582.0
Reactions
Betaine aldehyde + NAD + Water → Betaine + NADHdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
CHDH
Uniprot ID:
E1BES2
Molecular weight:
65518.0
Reactions
Choline + Acceptor → Betaine aldehyde + Reduced acceptordetails