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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-05-06 17:04:59 UTC
HMDB IDHMDB0001252
Secondary Accession Numbers
  • HMDB01252
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). In humans, betaine aldehyde is involved in betaine metabolism. Outside of the human body, betaine aldehyde has been detected, but not quantified in, several different foods, such as sourdoughs, summer savouries, loganberries, burbots, and celery stalks. This could make betaine aldehyde a potential biomarker for the consumption of these foods. Betaine aldehyde is an intermediate in the metabolism of glycine, serine, and threonine. The human aldehyde dehydrogenase (EC 1.2.1.3) facilitates the conversion of betaine aldehyde into glycine betaine. Betaine aldehyde is a substrate for choline dehydrogenase (PMID: 12467448 , 7646513 ).
Structure
Data?1588784699
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-9200000000-421de623448d638559baSpectrum
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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Tissue Locations
  • Epidermis
  • Kidney
  • Neuron
  • Placenta
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDBETALD
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 References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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. [PubMed:12467448 ]
  9. 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 ]
  10. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in oxidoreductase activity, acting on CH-OH group of donors
Specific function:
Not Available
Gene Name:
CHDH
Uniprot ID:
Q8NE62
Molecular weight:
65358.005
Reactions
Choline + acceptor → Betaine aldehyde + reduced acceptordetails
Choline + Acceptor → Betaine aldehyde + Reduced acceptordetails
General function:
Involved in oxidoreductase activity
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.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
Betaine aldehyde + NAD + Water → Betaine + NADHdetails
Betaine aldehyde + NAD + Water → Betaine + NADH + Hydrogen Iondetails
Betaine aldehyde + NADP + Water → Betaine + NADPH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular weight:
39835.17
General function:
Involved in zinc ion binding
Specific function:
Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:
ADH7
Uniprot ID:
P40394
Molecular weight:
41480.985
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular weight:
39858.37
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH6
Uniprot ID:
P28332
Molecular weight:
39072.275
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1C
Uniprot ID:
P00326
Molecular weight:
39867.27