Bovine Metabolome Database: Showing metabocard for Betaine aldehyde (BMDB0001252)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:43:05 UTC

Update Date

2020-05-21 16:28:30 UTC

BMDB ID

BMDB0001252

Secondary Accession Numbers

BMDB01252

Metabolite Identification

Common Name

Betaine aldehyde

Description

Betaine 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Glycine betaine aldehyde	ChEBI
(Formylmethyl)trimethyl-ammonium	HMDB
(Formylmethyl)trimethylammonium	HMDB
BTL	HMDB
N,N,N-Trimethyl-2-oxo ethanaminium	HMDB
N,N,N-Trimethyl-2-oxo-ethanaminium	HMDB
Trimethyl(formylmethyl)ammonium	HMDB
Betaine aldehyde	HMDB
N,N,N-Trimethyl-2-oxoethanaminium	HMDB

Chemical Formula

C₅H₁₂NO

Average Molecular Weight

102.1549

Monoisotopic Molecular Weight

102.091889011

IUPAC Name

trimethyl(2-oxoethyl)azanium

Traditional Name

betaine aldehyde

CAS Registry Number

7418-61-3

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 Key

SXKNCCSPZDCRFD-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Tetraalkylammonium 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 Framework

Aliphatic acyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:15710 )
a small molecule (BETAINE_ALDEHYDE )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.7	ALOGPS
logP	-4.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-8.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.06 m³·mol⁻¹	ChemAxon
Polarizability	11.64 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pb9-9200000000-421de623448d638559ba	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0pb9-9400000000-f6a6158eae2887c8c1b6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-a88ccc4efc693cee968e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-1900000000-c0d04b882f6ce11b3cd0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-3900000000-4f77db778fd255f71dd2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9100000000-5c1b81d01b1990f7dca0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-692d4006b060a156af58	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, positive	splash10-0a4i-9000000000-a0f8f51b132a9c6b49fe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-0f6x-9400000000-22287f9ceaea3897977a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-0udl-9700000000-d1b3630f59ab06687bec	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-0udl-9700000000-5daee890b99e88ca3863	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-0zfu-9500000000-ad58eac6d9e695625dfd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0a4l-9200000000-cd66506aaa5b99e64441	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-0a4l-9100000000-9d37cb03fd6c5fcec3e6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-0a4i-9000000000-7a7c6e00e7abea9f0814	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-0a4i-9000000000-651a97bfe861cc4973f7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-0a4i-9000000000-59d7cad20ff065ba2f6f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-0a4i-9000000000-485481563cd89be3d736	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0a4i-9000000000-c2ada75b19fab2af1a11	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-0a4i-9000000000-9235a6f53edfdaa4de3e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-0a4i-9000000000-e42443a076dcb59982c9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0a4i-9000000000-7d7369273ce75b201fbe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 45V, positive	splash10-0a4l-9000000000-2a95a181dc0fc993aaa3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-b4d3df384d18e299514f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-9700000000-1e9685e60dac71951689	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00e9-9000000000-766e4b072c03c25f1477	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Epidermis
Kidney
Neuron
Placenta

Pathways

Name	SMPDB/Pathwhiz	KEGG
Betaine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001252

DrugBank ID

DB04401

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022513

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15710

References

Synthesis Reference

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Alpha-aminoadipic semialdehyde dehydrogenase

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 + NADH	details

Enzyme Details

2. Choline dehydrogenase

General function:: Not Available
Specific function:: Not Available
Gene Name:: CHDH
Uniprot ID:: E1BES2
Molecular weight:: 65518.0

Reactions

Choline + Acceptor → Betaine aldehyde + Reduced acceptor	details

Showing metabocard for Betaine aldehyde (BMDB0001252)

Structure for BMDB0001252 (Betaine aldehyde)

Enzymes

Reactions

Reactions