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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-08-06 20:49:14 UTC
HMDB IDHMDB01080
Secondary Accession Numbers
  • HMDB60247
Metabolite Identification
Common Name4-Aminobutyraldehyde
Description4-Aminobutyraldehyde is a metabolite of putrescine. It is a substrate of human liver aldehyde dehydrogenase (EC 1.2.1.3) cytoplasmic (E1) and mitochondrial (E2) isozymes (PMID 3324802 ).
Structure
Thumb
Synonyms
  1. 4-Amino-butanal
  2. 4-Amino-butyraldehyde
  3. 4-Aminobutanal
  4. 4-Aminobutyraldehyde
  5. 4-Ammoniobutanal
  6. gamma-Aminobutyraldehyde
Chemical FormulaC4H9NO
Average Molecular Weight87.1204
Monoisotopic Molecular Weight87.068413915
IUPAC Name4-aminobutanal
Traditional Name4-aminobutanal
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
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlkylamines
Sub ClassN/A
Other Descriptors
  • Aldehydes
  • aminobutanal(ChEBI)
Substituents
  • N/A
Direct ParentAlkylamines
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility259 g/LALOGPS
logP-0.73ALOGPS
logP-0.78ChemAxon
logS0.47ALOGPS
pKa (Strongest Acidic)14.83ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.53ChemAxon
Polarizability9.72ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Liver
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022412
KNApSAcK IDNot Available
Chemspider ID115
KEGG Compound IDC00555
BioCyc ID4-AMINO-BUTYRALDEHYDE
BiGG ID35337
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01080
Metagene LinkHMDB01080
METLIN ID3225
PubChem Compound118
PDB IDNot Available
ChEBI ID17769
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 Mar 3. doi: 10.1038/nbt.2488. Pubmed: 23455439

Enzymes

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
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
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
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
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
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
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