Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-28 18:16:31 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 An omega-aminoaldehyde that is butanal in which one of the hydrogens of the terminal methyl group has been replaced by an amino group.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?1588097791
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
Disposition

Biological location

Source

Route of exposure

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
PropertyValueSource
Water Solubility259 g/LALOGPS
logP10(-0.73) g/LALOGPS
logP10(-0.78) g/LChemAxon
logS10(0.47) g/LALOGPS
pKa (Strongest Acidic)14.83ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.53 m³·mol⁻¹ChemAxon
Polarizability9.72 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+116.70831661259
DarkChem[M-H]-110.48231661259
AllCCS[M+H]+123.21432859911
AllCCS[M-H]-127.36932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-AminobutyraldehydeNCCCC=O1460.6Standard polar33892256
4-AminobutyraldehydeNCCCC=O791.5Standard non polar33892256
4-AminobutyraldehydeNCCCC=O844.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Aminobutyraldehyde,1TMS,isomer #1C[Si](C)(C)OC=CCCN1052.5Semi standard non polar33892256
4-Aminobutyraldehyde,1TMS,isomer #1C[Si](C)(C)OC=CCCN1048.7Standard non polar33892256
4-Aminobutyraldehyde,1TMS,isomer #1C[Si](C)(C)OC=CCCN1633.9Standard polar33892256
4-Aminobutyraldehyde,1TMS,isomer #2C[Si](C)(C)NCCCC=O1099.8Semi standard non polar33892256
4-Aminobutyraldehyde,1TMS,isomer #2C[Si](C)(C)NCCCC=O1091.1Standard non polar33892256
4-Aminobutyraldehyde,1TMS,isomer #2C[Si](C)(C)NCCCC=O1386.1Standard polar33892256
4-Aminobutyraldehyde,2TMS,isomer #1C[Si](C)(C)NCCC=CO[Si](C)(C)C1252.5Semi standard non polar33892256
4-Aminobutyraldehyde,2TMS,isomer #1C[Si](C)(C)NCCC=CO[Si](C)(C)C1268.3Standard non polar33892256
4-Aminobutyraldehyde,2TMS,isomer #1C[Si](C)(C)NCCC=CO[Si](C)(C)C1321.2Standard polar33892256
4-Aminobutyraldehyde,2TMS,isomer #2C[Si](C)(C)N(CCCC=O)[Si](C)(C)C1311.0Semi standard non polar33892256
4-Aminobutyraldehyde,2TMS,isomer #2C[Si](C)(C)N(CCCC=O)[Si](C)(C)C1300.2Standard non polar33892256
4-Aminobutyraldehyde,2TMS,isomer #2C[Si](C)(C)N(CCCC=O)[Si](C)(C)C1342.9Standard polar33892256
4-Aminobutyraldehyde,3TMS,isomer #1C[Si](C)(C)OC=CCCN([Si](C)(C)C)[Si](C)(C)C1475.3Semi standard non polar33892256
4-Aminobutyraldehyde,3TMS,isomer #1C[Si](C)(C)OC=CCCN([Si](C)(C)C)[Si](C)(C)C1448.4Standard non polar33892256
4-Aminobutyraldehyde,3TMS,isomer #1C[Si](C)(C)OC=CCCN([Si](C)(C)C)[Si](C)(C)C1368.6Standard polar33892256
4-Aminobutyraldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCN1277.1Semi standard non polar33892256
4-Aminobutyraldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCN1268.9Standard non polar33892256
4-Aminobutyraldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCN1785.2Standard polar33892256
4-Aminobutyraldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCCC=O1329.1Semi standard non polar33892256
4-Aminobutyraldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCCC=O1317.1Standard non polar33892256
4-Aminobutyraldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCCC=O1489.2Standard polar33892256
4-Aminobutyraldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCC=CO[Si](C)(C)C(C)(C)C1689.4Semi standard non polar33892256
4-Aminobutyraldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCC=CO[Si](C)(C)C(C)(C)C1700.3Standard non polar33892256
4-Aminobutyraldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCC=CO[Si](C)(C)C(C)(C)C1584.8Standard polar33892256
4-Aminobutyraldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCC=O)[Si](C)(C)C(C)(C)C1709.1Semi standard non polar33892256
4-Aminobutyraldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCC=O)[Si](C)(C)C(C)(C)C1703.4Standard non polar33892256
4-Aminobutyraldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCC=O)[Si](C)(C)C(C)(C)C1549.0Standard polar33892256
4-Aminobutyraldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2065.7Semi standard non polar33892256
4-Aminobutyraldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2064.6Standard non polar33892256
4-Aminobutyraldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1708.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Aminobutyraldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-94697e4ef2bcd3d60d5e2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Aminobutyraldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobutyraldehyde 10V, Positive-QTOFsplash10-00dr-9000000000-fd2685ec491cf38768ee2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobutyraldehyde 20V, Positive-QTOFsplash10-00di-9000000000-60f7776b7139a61c4f4b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobutyraldehyde 40V, Positive-QTOFsplash10-0006-9000000000-6e8079ea34a19e4872b52015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobutyraldehyde 10V, Negative-QTOFsplash10-000i-9000000000-e49664a7c668c7c296942015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobutyraldehyde 20V, Negative-QTOFsplash10-000i-9000000000-a83b936ba2b53f85e38a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobutyraldehyde 40V, Negative-QTOFsplash10-0006-9000000000-b0d6add4724e3c8624ec2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobutyraldehyde 10V, Positive-QTOFsplash10-00dl-9000000000-884ccf15aae061d40a592021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobutyraldehyde 20V, Positive-QTOFsplash10-0006-9000000000-2b042b066a8512d7a90f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobutyraldehyde 40V, Positive-QTOFsplash10-0006-9000000000-d74d71aeb5b03e31d4032021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobutyraldehyde 10V, Negative-QTOFsplash10-000i-9000000000-cac7a5f55f0489e13d412021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobutyraldehyde 20V, Negative-QTOFsplash10-014r-9000000000-a11930dc09365c6544912021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobutyraldehyde 40V, Negative-QTOFsplash10-0006-9000000000-c5fd6cf3b0d48066b65c2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
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

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