ECMDB: L-2-Amino-3-oxobutanoic acid (ECMDB06454) (M2MDB000671)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (276)

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

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:

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 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	25.53 m³·mol⁻¹	ChemAxon
Polarizability	10.47 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:

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

Protein Details

1. L-threonine 3-dehydrogenase

General function:: Involved in zinc ion binding
Specific function:: L-threonine + NAD(+) = L-2-amino-3- oxobutanoate + NADH
Gene Name:: tdh
Uniprot ID:: P07913
Molecular weight:: 37239

Reactions

L-threonine + NAD(+) = L-2-amino-3-oxobutanoate + NADH.

Protein Details

2. 2-amino-3-ketobutyrate coenzyme A ligase

General function:: Involved in glycine C-acetyltransferase activity
Specific function:: Catalyzes the cleavage of 2-amino-3-ketobutyrate to glycine and acetyl-CoA
Gene Name:: kbl
Uniprot ID:: P0AB77
Molecular weight:: 43117

Reactions

Acetyl-CoA + glycine = CoA + 2-amino-3-oxobutanoate.

Protein Details

3. NADP-dependent L-serine/L-allo-threonine dehydrogenase ydfG

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADP-dependent oxidation of L-allo- threonine to L-2-amino-3-keto-butyrate, which is spontaneously decarboxylated into aminoacetone. Also acts on L-serine, D-serine, D-threonine, D-3-hydroxyisobutyrate, L-3-hydroxyisobutyrate, D- glycerate and L-glycerate
Gene Name:: ydfG
Uniprot ID:: P39831
Molecular weight:: 27249

Reactions

3-hydroxypropanoate + NADP(+) = 3-oxopropanoate + NADPH.

L-2-Amino-3-oxobutanoic acid (ECMDB06454) (M2MDB000671)

Structure for #<Compound:0x6dffa038>

Enzymes

Reactions

Reactions

Reactions