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Showing metabocard for Betaine aldehyde (HMDB0001252)

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Record Information
Version5.0
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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001252 (Betaine aldehyde)

  Mrv1652306222023512D          

  7  6  0  0  0  0            999 V2000
    2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
M  CHG  1   6   1
M  END
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3D MOL for HMDB0001252 (Betaine aldehyde)

HMDB0001252
     RDKit          3D
Betaine aldehyde
 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.3148   -0.8089   -0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2624   -0.0076   -0.0161 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.4218   -0.2105    1.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011    1.3587   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9904   -0.5008   -0.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1612    0.1292    0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2658   -0.2338   -0.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2783   -0.2931   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3171   -1.8013   -0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0218   -0.9408   -1.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4634    0.1199    1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.4073    2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -1.2849    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1159    1.4215   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1426    1.8115    0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4114    1.9419   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0316   -1.6037   -0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9860   -0.3850   -1.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0723    0.8803    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
M  CHG  1   2   1
M  END
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3D SDF for HMDB0001252 (Betaine aldehyde)

  Mrv1652306222023512D          

  7  6  0  0  0  0            999 V2000
    2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
M  CHG  1   6   1
M  END
> <DATABASE_ID>
HMDB0001252

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C5H12NO

> <MOLECULAR_WEIGHT>
102.1549

> <EXACT_MASS>
102.091889011

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
11.63573187359404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
trimethyl(2-oxoethyl)azanium

> <ALOGPS_LOGP>
-2.69

> <JCHEM_LOGP>
-4.6528000948050785

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-8.17672175984932

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
41.0609

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
betaine aldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0001252 (Betaine aldehyde)

HMDB0001252
     RDKit          3D
Betaine aldehyde
 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.3148   -0.8089   -0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2624   -0.0076   -0.0161 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.4218   -0.2105    1.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011    1.3587   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9904   -0.5008   -0.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1612    0.1292    0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2658   -0.2338   -0.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2783   -0.2931   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3171   -1.8013   -0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0218   -0.9408   -1.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4634    0.1199    1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.4073    2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -1.2849    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1159    1.4215   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1426    1.8115    0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4114    1.9419   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0316   -1.6037   -0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9860   -0.3850   -1.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0723    0.8803    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
M  CHG  1   2   1
M  END
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PDB for HMDB0001252 (Betaine aldehyde)

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0       5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850   0.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850  -2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       3.850  -1.334   0.000  0.00  0.00           N+1
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    6                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    1    2    3    4                                             
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0001252 (Betaine aldehyde)

COMPND    HMDB0001252
HETATM    1  C1  UNL     1      -1.315  -0.809  -0.658  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.262  -0.008  -0.016  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -0.422  -0.210   1.409  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.501   1.359  -0.393  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.990  -0.501  -0.522  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.161   0.129   0.140  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.266  -0.234  -0.231  1.00  0.00           O  
HETATM    8  H1  UNL     1      -2.278  -0.293  -0.636  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.317  -1.801  -0.161  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.022  -0.941  -1.726  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.463   0.120   1.655  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.247   0.407   2.019  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.326  -1.285   1.617  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.116   1.421  -1.333  1.00  0.00           H  
HETATM   15  H8  UNL     1      -1.143   1.812   0.402  1.00  0.00           H  
HETATM   16  H9  UNL     1       0.411   1.942  -0.550  1.00  0.00           H  
HETATM   17  H10 UNL     1       1.032  -1.604  -0.326  1.00  0.00           H  
HETATM   18  H11 UNL     1       0.986  -0.385  -1.612  1.00  0.00           H  
HETATM   19  H12 UNL     1       2.072   0.880   0.920  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    4    5
CONECT    3   11   12   13
CONECT    4   14   15   16
CONECT    5    6   17   18
CONECT    6    7    7   19
END
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SMILES for HMDB0001252 (Betaine aldehyde)

C[N+](C)(C)CC=O
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INCHI for HMDB0001252 (Betaine aldehyde)

InChI=1S/C5H12NO/c1-6(2,3)4-5-7/h5H,4H2,1-3H3/q+1
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View in JSmolView NMR AssignmentsView Stereo Labels
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos117.18230932474
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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
MarkerDB IDNot Available
Good Scents IDNot Available
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

Enzymes

Enzyme Details
1. Choline dehydrogenase, mitochondrial
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
Enzyme Details
2. Alpha-aminoadipic semialdehyde dehydrogenase
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
Enzyme Details
3. Alcohol dehydrogenase class-3
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
Enzyme Details
4. Alcohol dehydrogenase 1B
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular weight:
39835.17
Enzyme Details
5. Alcohol dehydrogenase class 4 mu/sigma chain
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
Enzyme Details
6. Alcohol dehydrogenase 1A
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular weight:
39858.37
Enzyme Details
7. Alcohol dehydrogenase 6
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH6
Uniprot ID:
P28332
Molecular weight:
39072.275
Enzyme Details
8. Alcohol dehydrogenase 1C
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1C
Uniprot ID:
P00326
Molecular weight:
39867.27