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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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x9ec22628> Close
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	Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
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:	1
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 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 24.53 m³·mol⁻¹ ChemAxon Polarizability 9.72 ų 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:	4-Aminobutyraldehyde + Water + NAD <> gamma-Aminobutyric acid +2 Hydrogen ion + NADH alpha-Ketoglutarate + Putrescine > 4-Aminobutyraldehyde + L-Glutamate Putrescine + alpha-Ketoglutarate <> 4-Aminobutyraldehyde + L-Glutamate 4-Aminobutyraldehyde + NAD + Water <> gamma-Aminobutyric acid + NADH + Hydrogen ion 4-Aminobutyraldehyde > 1-Pyrroline + Water 4-Aminobutyraldehyde + NAD + Water > gamma-Aminobutyric acid + NADH + Hydrogen ion Putrescine + Oxoglutaric acid <> 4-Aminobutyraldehyde + L-Glutamate 4-Aminobutyraldehyde + NAD + Water > gamma-Aminobutyric acid + NADH Ethylenediamine + alpha-Ketoglutarate + 4-Aminobutyraldehyde <> 1-Pyrroline + L-Glutamate + Water Putrescine + Oxoglutaric acid > L-Glutamic acid + 4-Aminobutyraldehyde + L-Glutamate
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