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4-aminobutanal (YMDB00587)

Identification
YMDB IDYMDB00587
Name4-aminobutanal
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 4-amino-butanal
  • 4-amino-butyraldehyde
  • 4-Aminobutanal
  • 4-aminobutyraldehyde
  • ABAL
  • Butyraldehyde, 4-amino-
  • gamma-aminobutanal
  • gamma-aminobutyraldehyde
  • 4-Ammoniobutanal
CAS number4390-05-0
WeightAverage: 87.1204
Monoisotopic: 87.068413915
InChI KeyDZQLQEYLEYWJIB-UHFFFAOYSA-N
InChIInChI=1S/C4H9NO/c5-3-1-2-4-6/h4H,1-3,5H2
IUPAC Name4-aminobutanal
Traditional IUPAC Nameω-aminoaldehyde
Chemical FormulaC4H9NO
SMILES[H]C(=O)CCCN
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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 Area43.09 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.53 m³·mol⁻¹ChemAxon
Polarizability9.72 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
beta-Alanine metabolismec00410 Map00410
SMPDB ReactionsNot Available
KEGG Reactions
NAD + 4-aminobutanal + water → NADH + gamma-Aminobutyric acid + hydron
Spermidine + Ubiquinone-6 + water → 1,3-Diaminopropane + Ubiquinol-6 + 4-aminobutanal
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-94697e4ef2bcd3d60d5eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-9000000000-fd2685ec491cf38768eeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-60f7776b7139a61c4f4bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-6e8079ea34a19e4872b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-e49664a7c668c7c29694JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-a83b936ba2b53f85e38aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b0d6add4724e3c8624ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-9000000000-884ccf15aae061d40a59JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-2b042b066a8512d7a90fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-d74d71aeb5b03e31d403JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-cac7a5f55f0489e13d41JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-9000000000-a11930dc09365c654491JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c5fd6cf3b0d48066b65cJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Asakura, 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.
External Links:
ResourceLink
CHEBI ID17769
HMDB IDHMDB01080
Pubchem Compound ID118
Kegg IDC00555
ChemSpider ID115
FOODB IDFDB022412
Wikipedia IDNot Available
BioCyc ID4-AMINO-BUTYRALDEHYDE

Enzymes

Protein Details
1. Potassium-activated aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(+) + H(2)O = an acid + NADH
Gene Name:
ALD4
Uniprot ID:
P46367
Molecular weight:
56723.19922
Reactions
An aldehyde + NAD(+) + H(2)O → an acid + NADH.
Protein Details
2. Aldehyde dehydrogenase 5, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Minor mitochondrial aldehyde dehydrogenase isoform. Plays a role in regulation or biosynthesis of electron transport chain components. Involved in the biosynthesis of acetate during anaerobic growth on glucose
Gene Name:
ALD5
Uniprot ID:
P40047
Molecular weight:
56620.39844
Reactions
An aldehyde + NAD(+) + H(2)O → an acid + NADH.
An aldehyde + NADP(+) + H(2)O → an acid + NADPH.
Protein Details
3. Deoxyhypusine synthase
General function:
Involved in peptidyl-lysine modification to hypusine
Specific function:
Catalyzes the NAD-dependent oxidative cleavage of spermidine and the subsequent transfer of the butylamine moiety of spermidine to the epsilon-amino group of a specific lysine residue of the eIF-5A precursor protein to form the intermediate deoxyhypusine residue
Gene Name:
DYS1
Uniprot ID:
P38791
Molecular weight:
42891.80078
Reactions
[eIF5A-precursor]-lysine + spermidine → [eIF5A-precursor]-deoxyhypusine + propane-1,3-diamine.