4-aminobutanal (YMDB00587)

Identification

YMDB ID

YMDB00587

Name

4-aminobutanal

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

4-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

MOL SDF PDB SMILES InChI

Synonyms

4-amino-butanal
4-amino-butyraldehyde
4-Aminobutanal
4-aminobutyraldehyde
ABAL
Butyraldehyde, 4-amino-
gamma-aminobutanal
gamma-aminobutyraldehyde
4-Ammoniobutanal

CAS number

4390-05-0

Weight

Average: 87.1204
Monoisotopic: 87.068413915

InChI Key

DZQLQEYLEYWJIB-UHFFFAOYSA-N

InChI

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

IUPAC Name

4-aminobutanal

Traditional IUPAC Name

ω-aminoaldehyde

Chemical Formula

C₄H₉NO

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-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 Framework

Aliphatic acyclic compounds

External Descriptors

aminobutanal (CHEBI:17769 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	259 g/L	ALOGPS
logP	-0.73	ALOGPS
logP	-0.78	ChemAxon
logS	0.47	ALOGPS
pKa (Strongest Acidic)	14.83	ChemAxon
pKa (Strongest Basic)	9.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	24.53 m³·mol⁻¹	ChemAxon
Polarizability	9.72 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

mitochondrion
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

beta-Alanine metabolism

PW002381

KEGG Pathways

Arginine and proline metabolism	ec00330
beta-Alanine metabolism	ec00410

SMPDB Reactions

Not 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 Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-94697e4ef2bcd3d60d5e	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-9000000000-fd2685ec491cf38768ee	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-60f7776b7139a61c4f4b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-6e8079ea34a19e4872b5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-e49664a7c668c7c29694	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-a83b936ba2b53f85e38a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-b0d6add4724e3c8624ec	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-9000000000-884ccf15aae061d40a59	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-2b042b066a8512d7a90f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-d74d71aeb5b03e31d403	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-cac7a5f55f0489e13d41	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-9000000000-a11930dc09365c654491	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-c5fd6cf3b0d48066b65c	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	17769
HMDB ID	HMDB01080
Pubchem Compound ID	118
Kegg ID	C00555
ChemSpider ID	115
FOODB ID	FDB022412
Wikipedia ID	Not Available
BioCyc ID	4-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.

Structure for #<Compound:0xa32a5e38>

Enzymes

Reactions

Reactions

Reactions