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Showing metabocard for 4-Aminobutyraldehyde (HMDB0001080)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:25 UTC
HMDB IDHMDB0001080
Secondary Accession Numbers
  • HMDB0060247
  • HMDB01080
  • HMDB60247
Metabolite Identification
Common Name4-Aminobutyraldehyde
Description4-Aminobutyraldehyde, also known as 4-amino-butanal, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. 4-Aminobutyraldehyde is a very strong basic compound (based on its pKa). 4-Aminobutyraldehyde exists in all living species, ranging from bacteria to humans. Outside of the human body, 4-Aminobutyraldehyde has been detected, but not quantified in, several different foods, such as chinese bayberries, sour cherries, romaine lettuces, black salsifies, and green zucchinis. This could make 4-aminobutyraldehyde a potential biomarker for the consumption of these foods. An omega-aminoaldehyde that is butanal in which one of the hydrogens of the terminal methyl group has been replaced by an amino group.
Structure
Data?1676999725
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001080 (4-Aminobutyraldehyde)

  Mrv0541 02231218552D          

  6  5  0  0  0  0            999 V2000
   -0.3562    0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726    0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850    0.2046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850   -0.2046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
M  END
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3D MOL for HMDB0001080 (4-Aminobutyraldehyde)

HMDB0001080
     RDKit          3D
4-Aminobutyraldehyde
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.8687    0.8184   -0.0129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562   -0.5789   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0785   -0.6396    0.5234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    0.2174   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538    0.1806    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1422    0.8252   -0.1988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727    1.2677   -0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3240    1.3551    0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4978   -0.9008   -1.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1507   -1.1833    0.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -1.7121    0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1642   -0.3268    1.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4617    1.2391   -0.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9422   -0.1493   -1.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864   -0.4126    1.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
M  END
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3D SDF for HMDB0001080 (4-Aminobutyraldehyde)

  Mrv0541 02231218552D          

  6  5  0  0  0  0            999 V2000
   -0.3562    0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726    0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850    0.2046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850   -0.2046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001080

> <DATABASE_NAME>
hmdb

> <SMILES>
NCCCC=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO/c5-3-1-2-4-6/h4H,1-3,5H2

> <INCHI_KEY>
DZQLQEYLEYWJIB-UHFFFAOYSA-N

> <FORMULA>
C4H9NO

> <MOLECULAR_WEIGHT>
87.1204

> <EXACT_MASS>
87.068413915

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
9.71572746213239

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-aminobutanal

> <ALOGPS_LOGP>
-0.73

> <JCHEM_LOGP>
-0.780417868

> <ALOGPS_LOGS>
0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.828866437700317

> <JCHEM_PKA_STRONGEST_BASIC>
9.792866479907637

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
24.532400000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ω-aminoaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001080 (4-Aminobutyraldehyde)

HMDB0001080
     RDKit          3D
4-Aminobutyraldehyde
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.8687    0.8184   -0.0129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562   -0.5789   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0785   -0.6396    0.5234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    0.2174   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538    0.1806    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1422    0.8252   -0.1988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727    1.2677   -0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3240    1.3551    0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4978   -0.9008   -1.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1507   -1.1833    0.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -1.7121    0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1642   -0.3268    1.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4617    1.2391   -0.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9422   -0.1493   -1.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864   -0.4126    1.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
M  END
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PDB for HMDB0001080 (4-Aminobutyraldehyde)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.665   0.382   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.665  -0.382   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.002  -0.382   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.002   0.382   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -3.332   0.382   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0       3.332  -0.382   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0001080 (4-Aminobutyraldehyde)

COMPND    HMDB0001080
HETATM    1  N1  UNL     1      -1.869   0.818  -0.013  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.456  -0.579  -0.073  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.078  -0.640   0.523  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.899   0.217  -0.239  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.254   0.181   0.317  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.142   0.825  -0.199  1.00  0.00           O  
HETATM    7  H1  UNL     1      -1.873   1.268  -0.954  1.00  0.00           H  
HETATM    8  H2  UNL     1      -1.324   1.355   0.699  1.00  0.00           H  
HETATM    9  H3  UNL     1      -1.498  -0.901  -1.126  1.00  0.00           H  
HETATM   10  H4  UNL     1      -2.151  -1.183   0.544  1.00  0.00           H  
HETATM   11  H5  UNL     1       0.228  -1.712   0.547  1.00  0.00           H  
HETATM   12  H6  UNL     1      -0.164  -0.327   1.585  1.00  0.00           H  
HETATM   13  H7  UNL     1       0.462   1.239  -0.287  1.00  0.00           H  
HETATM   14  H8  UNL     1       0.942  -0.149  -1.280  1.00  0.00           H  
HETATM   15  H9  UNL     1       2.486  -0.413   1.186  1.00  0.00           H  
CONECT    1    2    7    8
CONECT    2    3    9   10
CONECT    3    4   11   12
CONECT    4    5   13   14
CONECT    5    6    6   15
END
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SMILES for HMDB0001080 (4-Aminobutyraldehyde)

NCCCC=O
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INCHI for HMDB0001080 (4-Aminobutyraldehyde)

InChI=1S/C4H9NO/c5-3-1-2-4-6/h4H,1-3,5H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4-Amino-butyraldehydeChEBI
4-Amino-butanalHMDB
4-AminobutanalHMDB
4-AmmoniobutanalHMDB
gamma-AminobutyraldehydeHMDB
4-AminobutyraldehydeChEBI
Chemical FormulaC4H9NO
Average Molecular Weight87.1204
Monoisotopic Molecular Weight87.068413915
IUPAC Name4-aminobutanal
Traditional Nameω-aminoaldehyde
CAS Registry Number4390-05-0
SMILES
NCCCC=O
InChI Identifier
InChI=1S/C4H9NO/c5-3-1-2-4-6/h4H,1-3,5H2
InChI KeyDZQLQEYLEYWJIB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022412
KNApSAcK IDC00019656
Chemspider ID115
KEGG Compound IDC02903
BioCyc ID4-AMINO-BUTYRALDEHYDE
BiGG ID35337
Wikipedia LinkNot Available
METLIN ID3225
PubChem Compound118
PDB IDNot Available
ChEBI ID17769
Food Biomarker OntologyNot Available
VMH ID4ABUTN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAsakura, Tadashi; Takada, Koji; Ikeda, Yoshitaka; Matsuda, Makoto. Preparation of 4-aminobutyraldehyde and its properties on ion exchange chromatography. Jikeikai Medical Journal (1988), 35(1), 23-31.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kikonyogo A, Pietruszko R: Aldehyde dehydrogenase from adult human brain that dehydrogenates gamma-aminobutyraldehyde: purification, characterization, cloning and distribution. Biochem J. 1996 May 15;316 ( Pt 1):317-24. [PubMed:8645224 ]
  2. Kurys G, Shah PC, Kikonygo A, Reed D, Ambroziak W, Pietruszko R: Human aldehyde dehydrogenase. cDNA cloning and primary structure of the enzyme that catalyzes dehydrogenation of 4-aminobutyraldehyde. Eur J Biochem. 1993 Dec 1;218(2):311-20. [PubMed:8269919 ]
  3. McPherson JD, Wasmuth JJ, Kurys G, Pietruszko R: Human aldehyde dehydrogenase: chromosomal assignment of the gene for the isozyme that metabolizes gamma-aminobutyraldehyde. Hum Genet. 1994 Feb;93(2):211-2. [PubMed:8112751 ]
  4. Ambroziak W, Kurys G, Pietruszko R: Aldehyde dehydrogenase (EC 1.2.1.3): comparison of subcellular localization of the third isozyme that dehydrogenates gamma-aminobutyraldehyde in rat, guinea pig and human liver. Comp Biochem Physiol B. 1991;100(2):321-7. [PubMed:1799975 ]
  5. Ambroziak W, Pietruszko R: Human aldehyde dehydrogenase: metabolism of putrescine and histamine. Alcohol Clin Exp Res. 1987 Dec;11(6):528-32. [PubMed:3324802 ]
  6. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Enzymes

Enzyme Details
1. 4-trimethylaminobutyraldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
4-Aminobutyraldehyde + NAD + Water → gamma-Aminobutyric acid + NADHdetails
4-Aminobutyraldehyde + NADP + Water → gamma-Aminobutyric acid + NADPH + Hydrogen Iondetails
4-Aminobutyraldehyde + NAD + Water → gamma-Aminobutyric acid + NADH + Hydrogen Iondetails
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
4-Aminobutyraldehyde + NADP + Water → gamma-Aminobutyric acid + NADPH + Hydrogen Iondetails
4-Aminobutyraldehyde + NAD + Water → gamma-Aminobutyric acid + NADH + Hydrogen Iondetails
Enzyme Details
3. Aldehyde dehydrogenase family 1 member A3
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Enzyme Details
4. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
4-Aminobutyraldehyde + NADP + Water → gamma-Aminobutyric acid + NADPH + Hydrogen Iondetails
4-Aminobutyraldehyde + NAD + Water → gamma-Aminobutyric acid + NADH + Hydrogen Iondetails
Enzyme Details
5. Fatty aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
4-Aminobutyraldehyde + NADP + Water → gamma-Aminobutyric acid + NADPH + Hydrogen Iondetails
4-Aminobutyraldehyde + NAD + Water → gamma-Aminobutyric acid + NADH + Hydrogen Iondetails
Enzyme Details
6. Aldehyde dehydrogenase X, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
4-Aminobutyraldehyde + NADP + Water → gamma-Aminobutyric acid + NADPH + Hydrogen Iondetails
4-Aminobutyraldehyde + NAD + Water → gamma-Aminobutyric acid + NADH + Hydrogen Iondetails
Enzyme Details
7. Amiloride-sensitive amine oxidase [copper-containing]
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
Reactions
Putrescine + Oxygen + Water → 4-Aminobutyraldehyde + Ammonia + Hydrogen peroxidedetails