ECMDB: 4-Aminobutyraldehyde (ECMDB01080) (M2MDB000246)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (720)

Record Information

Version

2.0

Creation Date

2012-05-31 13:44:48 -0600

Update Date

2015-06-04 15:14:16 -0600

Secondary Accession Numbers

ECMDB01080

Identification

Name:

4-Aminobutyraldehyde

Description

4-Aminobutyraldehyde is a metabolite of putrescine. In both arginine and proline metabolism, and beta-alanine metabolism, it is a substrate of aminobutyraldehyde dehydrogenase [EC:1.2.1.19]. It is converted to 4-aminobutanoate. (KEGG)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

γ-aminobutyraldehyde
4-Amino-butanal
4-Amino-butyraldehyde
4-Aminobutanal
4-Aminobutyraldehyde
ABAL
g-Aminobutyraldehyde
Gamma-Aminobutyraldehyde
γ-Aminobutyraldehyde

Chemical Formula:

C₄H₉NO

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

CAS number:

4390-05-0

IUPAC Name:

4-aminobutanal

Traditional IUPAC Name:

ω-aminoaldehyde

SMILES:

NCCCC=O

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	Source

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:

Cytoplasm

Reactions:

SMPDB Pathways:

arginine metabolism	PW000790
beta-Alanine metabolism	PW000896
ornithine metabolism	PW000791

KEGG Pathways:

Arginine and proline metabolism ec00330
beta-Alanine metabolism ec00410

EcoCyc Pathways:

putrescine degradation I PUTDEG-PWY

Concentrations

Not Available

Spectra

Spectra:

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

References

References:

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
Ambroziak W, Pietruszko R: Human aldehyde dehydrogenase: metabolism of putrescine and histamine. Alcohol Clin Exp Res. 1987 Dec;11(6):528-32. Pubmed: 3324802
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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
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
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
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
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

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.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17769
HMDB ID	HMDB01080
Pubchem Compound ID	118
Kegg ID	C00555
ChemSpider ID	115
Wikipedia ID	Not Available
BioCyc ID	4-AMINO-BUTYRALDEHYDE
EcoCyc ID	4-AMINO-BUTYRALDEHYDE

Enzymes

Protein Details

1. Putrescine aminotransferase

General function:: Involved in transaminase activity
Specific function:: Catalyzes the aminotransferase reaction from putrescine to 2-oxoglutarate, leading to glutamate and 4-aminobutanal, which spontaneously cyclizes to form 1-pyrroline. Is also able to transaminate cadaverine and, in lower extent, spermidine, but not ornithine. Alpha-ketobutyrate and pyruvate can also act as amino acceptors, although much less efficiently
Gene Name:: patA
Uniprot ID:: P42588
Molecular weight:: 49661

Reactions

Putrescine + 2-oxoglutarate = L-glutamate + 1-pyrroline + H(2)O.

Protein Details

2. Gamma-aminobutyraldehyde dehydrogenase

General function:: Involved in aminobutyraldehyde dehydrogenase activity
Specific function:: Catalyzes the oxidation of 1-pyrroline, which is spontaneously formed from 4-aminobutanal, leading to 4- aminobutanoate (GABA). Can also oxidize n-alkyl medium-chain aldehydes, but with a lower catalytic efficiency
Gene Name:: ydcW
Uniprot ID:: P77674
Molecular weight:: 50830

Reactions

4-aminobutanal + NAD(+) + H(2)O = 4-aminobutanoate + NADH.

4-Aminobutyraldehyde (ECMDB01080) (M2MDB000246)

Structure for #<Compound:0xa9a89ba8>

Enzymes

Reactions

Reactions