P. aeruginosa Metabolome Database: L-2-Amino-3-oxobutanoic acid (PAMDB000671)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000671

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 PDB SMILES InChI View 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

Average Molecular Weight:

117.1033

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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
Short-chain keto acid
Beta-keto acid
Amino fatty acid
Fatty acyl
1,3-dicarbonyl compound
Keto acid
Beta-hydroxy ketone
Alpha-aminoketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

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	206.0 mg/mL	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:

Pathways:

Glycine, serine and threonine metabolism pae00260
Pyrimidine metabolism pae00240

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
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

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

L-2-Amino-3-oxobutanoic acid (PAMDB000671)

Structure for L-2-Amino-3-oxobutanoic acid (PAMDB000671)