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Record Information
Version	2.0
Creation Date	2012-05-31 14:08:24 -0600
Update Date	2015-06-03 15:54:52 -0600
Secondary Accession Numbers	ECMDB06454
Identification
Name:	L-2-Amino-3-oxobutanoic acid
Description	L-2-Amino-3-oxobutanoic acid or L-2-amino acetic acid is involved in glycine/serine metabolism and is a breakdown product from glycine. It spontaneously decomposes to aminoacetone. Delta-aminolevuliinate synthase is the enzyme that catalyzes the interconversion between glycine and L-2-amino-3-oxobutanoic acid. Glycine C-acetyltransferase is also capable of catalyzing this reaction.
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa43805f0> Close
Synonyms:	α-amino-β-ketobutyrate α-amino-β-ketobutyric acid (2S)-2-amino-3-oxobutanoate (2S)-2-amino-3-oxobutanoic acid (S)-2-Amino-3-oxobutanoate (S)-2-Amino-3-oxobutanoic acid 2-Amino-3-ketobutyrate 2-Amino-3-ketobutyric acid 2-Amino-3-oxobutanoate 2-Amino-3-oxobutanoic acid 2-Amino-3-oxobutyrate 2-Amino-3-oxobutyric acid 2-Amino-acetoacetate 2-Amino-acetoacetic acid a-amino-b-Ketobutyrate a-amino-b-Ketobutyric acid Alpha-Amino-beta-ketobutyrate Alpha-Amino-beta-ketobutyric acid L-2-Amino acetate L-2-Amino acetic acid L-2-Amino-3-oxobutanoate L-2-Amino-3-oxobutanoic acid L-2-Amino-acetoacetate L-2-Amino-acetoacetic acid α-amino-β-Ketobutyrate α-amino-β-Ketobutyric acid
Chemical Formula:	C4H7NO3
Weight:	Average: 117.1033 Monoisotopic: 117.042593095
InChI Key:	SAUCHDKDCUROAO-VKHMYHEASA-N
InChI:	InChI=1S/C4H7NO3/c1-2(6)3(5)4(7)8/h3H,5H2,1H3,(H,7,8)/t3-/m0/s1
CAS number:	Not Available
IUPAC Name:	(2S)-2-amino-3-oxobutanoic acid
Traditional IUPAC Name:	2-amino-3-ketobutyric acid
SMILES:	CC(=O)[C@H](N)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	L-alpha-amino acids
Alternative Parents	Short-chain keto acids and derivatives Beta-keto acids and derivatives Beta-hydroxy ketones 1,3-dicarbonyl compounds Alpha-amino ketones Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
Substituents	L-alpha-amino acid Beta-keto acid Short-chain keto acid Beta-hydroxy ketone Keto acid 1,3-dicarbonyl compound Alpha-aminoketone Amino acid Ketone Carboxylic acid Monocarboxylic acid or derivatives Organic nitrogen compound Organonitrogen compound Organooxygen compound Primary aliphatic amine Primary amine Hydrocarbon derivative Organic oxide Carbonyl group Organopnictogen compound Organic oxygen compound Amine Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	non-proteinogenic L-alpha-amino acid (CHEBI:40673 ) 2-amino-3-oxobutanoic acid (CHEBI:40673 ) Oxo fatty acids (C03508 ) Oxo fatty acids (LMFA01060172 )
Physical Properties
State:	Solid
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 206 g/L ALOGPS logP -2.6 ALOGPS logP -3.1 ChemAxon logS 0.25 ALOGPS pKa (Strongest Acidic) 1.87 ChemAxon pKa (Strongest Basic) 7.25 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 80.39 Ų ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 25.53 m³·mol⁻¹ ChemAxon Polarizability 10.47 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:	L-Allothreonine + NADP <> L-2-Amino-3-oxobutanoic acid + Hydrogen ion + NADPH NAD + L-Threonine <> L-2-Amino-3-oxobutanoic acid + Hydrogen ion + NADH Acetyl-CoA + Glycine <> L-2-Amino-3-oxobutanoic acid + Coenzyme A L-2-Amino-3-oxobutanoic acid + Hydrogen ion > Aminoacetone + Carbon dioxide Glycine + Acetyl-CoA <> Hydrogen ion + L-2-Amino-3-oxobutanoic acid + Coenzyme A L-Threonine + NAD > Hydrogen ion + L-2-Amino-3-oxobutanoic acid + NADH Acetyl-CoA + Glycine > CoA + L-2-Amino-3-oxobutanoic acid L-Threonine + NAD > L-2-Amino-3-oxobutanoic acid + NADH L-Allothreonine + NADP + L-2-Amino-3-oxobutanoic acid <> Aminoacetone + Carbon dioxide + NADPH + Hydrogen ion L-Threonine + NAD + L-Threonine > Hydrogen ion + NADH + L-2-Amino-3-oxobutanoic acid L-2-Amino-3-oxobutanoic acid + Coenzyme A > Acetyl-CoA + Glycine
SMPDB Pathways:	L-threonine degradation to methylglyoxal PW002106 Pyrimidine metabolism PW000942 threonine biosynthesis PW000817
KEGG Pathways:	Glycine, serine and threonine metabolism ec00260 Pyrimidine metabolism ec00240
EcoCyc Pathways:	threonine degradation II THREONINE-DEG2-PWY threonine degradation III (to methylglyoxal) THRDLCTCAT-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-006x-9000000000-22150e9e4fa3d3433203 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-006y-9300000000-b1976cb0fd0e419923c4 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 splash10-0gi0-5900000000-1565f4db4a91c43d6697 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0fk9-9200000000-1dcade0f25d1eaa7da38 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0pb9-9100000000-ef438e90f9a367453dd6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014i-9800000000-e0bdda855b20afe7598c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00di-9200000000-95fb6afa14c1b9b751e7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00di-9000000000-210f3affcabb1713c4e3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00di-9000000000-b0afa4195d3cbff82f87 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00di-9000000000-c542fb4af78140fc2eaa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-5136afe8f7ab28631fe4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-01b9-4900000000-cbd7caa68b545994551b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00dj-9200000000-45cde5b7b6c52af1dee2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9000000000-1e9dea60f3fc6a6303f7 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:	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 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:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16944 HMDB ID HMDB06454 Pubchem Compound ID 5460100 Kegg ID C03508 ChemSpider ID 389046 Wikipedia ID Not Available BioCyc ID AMINO-OXOBUT EcoCyc ID AMINO-OXOBUT Ligand Expo AKB

Enzymes