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Showing metabocard for L-2-Amino-3-oxobutanoic acid (HMDB0006454)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 09:48:15 UTC
Update Date2023-02-21 17:17:18 UTC
HMDB IDHMDB0006454
Secondary Accession Numbers
  • HMDB06454
Metabolite Identification
Common NameL-2-Amino-3-oxobutanoic acid
DescriptionL-2-Amino-3-oxobutanoic acid, also known as L-2-amino-acetoacetate or 2-amino-3-ketobutyrIC ACID, 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. L-2-Amino-3-oxobutanoic acid exists in all living species, ranging from bacteria to plants to humans. In humans, L-2-amino-3-oxobutanoic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. L-2-Amino-3-oxobutanoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make L-2-amino-3-oxobutanoic acid a potential biomarker for the consumption of these foods. L-2-Amino-3-oxobutanoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on L-2-Amino-3-oxobutanoic acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006454 (L-2-Amino-3-oxobutanoic acid)

  Mrv0541 02231217162D          

  8  7  0  0  1  0            999 V2000
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for HMDB0006454 (L-2-Amino-3-oxobutanoic acid)

HMDB0006454
     RDKit          3D
L-2-Amino-3-oxobutanoic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    1.7374    0.6824   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7926   -0.4599   -0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959   -1.3330   -1.2031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880   -0.5793    0.4942 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1132   -1.7954    0.1790 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115    0.5612    0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4987    0.3384    0.0492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9428    1.8786    0.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3876    1.5123   -0.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7640    0.3978   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    1.0281    0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0526   -0.5968    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4227   -2.5761    0.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5305   -1.6648   -0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2885    2.6065    0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  1
  5 13  1  0
  5 14  1  0
  8 15  1  0
M  END
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3D SDF for HMDB0006454 (L-2-Amino-3-oxobutanoic acid)

  Mrv0541 02231217162D          

  8  7  0  0  1  0            999 V2000
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006454

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)[C@H](N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO3/c1-2(6)3(5)4(7)8/h3H,5H2,1H3,(H,7,8)/t3-/m0/s1

> <INCHI_KEY>
SAUCHDKDCUROAO-VKHMYHEASA-N

> <FORMULA>
C4H7NO3

> <MOLECULAR_WEIGHT>
117.1033

> <EXACT_MASS>
117.042593095

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
10.47020466024506

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-oxobutanoic acid

> <ALOGPS_LOGP>
-2.63

> <JCHEM_LOGP>
-3.0602758377471853

> <ALOGPS_LOGS>
0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.179862736987843

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8723113404422236

> <JCHEM_PKA_STRONGEST_BASIC>
7.249120732565084

> <JCHEM_POLAR_SURFACE_AREA>
80.39000000000001

> <JCHEM_REFRACTIVITY>
25.5346

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-ketobutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0006454 (L-2-Amino-3-oxobutanoic acid)

HMDB0006454
     RDKit          3D
L-2-Amino-3-oxobutanoic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    1.7374    0.6824   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7926   -0.4599   -0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959   -1.3330   -1.2031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880   -0.5793    0.4942 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1132   -1.7954    0.1790 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115    0.5612    0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4987    0.3384    0.0492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9428    1.8786    0.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3876    1.5123   -0.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7640    0.3978   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    1.0281    0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0526   -0.5968    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4227   -2.5761    0.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5305   -1.6648   -0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2885    2.6065    0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  1
  5 13  1  0
  5 14  1  0
  8 15  1  0
M  END
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PDB for HMDB0006454 (L-2-Amino-3-oxobutanoic acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   2.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.850   1.334   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0006454 (L-2-Amino-3-oxobutanoic acid)

COMPND    HMDB0006454
HETATM    1  C1  UNL     1       1.737   0.682  -0.304  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.793  -0.460  -0.384  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.996  -1.333  -1.203  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.388  -0.579   0.494  1.00  0.00           C  
HETATM    5  N1  UNL     1      -1.113  -1.795   0.179  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.311   0.561   0.378  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.499   0.338   0.049  1.00  0.00           O  
HETATM    8  O3  UNL     1      -0.943   1.879   0.612  1.00  0.00           O  
HETATM    9  H1  UNL     1       1.388   1.512  -0.936  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.764   0.398  -0.647  1.00  0.00           H  
HETATM   11  H3  UNL     1       1.871   1.028   0.757  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.053  -0.597   1.576  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.423  -2.576   0.199  1.00  0.00           H  
HETATM   14  H6  UNL     1      -1.531  -1.665  -0.772  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.289   2.607   0.001  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    4
CONECT    4    5    6   12
CONECT    5   13   14
CONECT    6    7    7    8
CONECT    8   15
END
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SMILES for HMDB0006454 (L-2-Amino-3-oxobutanoic acid)

CC(=O)[C@H](N)C(O)=O
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INCHI for HMDB0006454 (L-2-Amino-3-oxobutanoic acid)

InChI=1S/C4H7NO3/c1-2(6)3(5)4(7)8/h3H,5H2,1H3,(H,7,8)/t3-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(S)-2-Amino-3-oxobutanoic acidChEBI
2-AMINO-3-ketobutyrIC ACIDChEBI
L-2-Amino-3-oxobutanoateChEBI
L-2-Amino-acetoacetateChEBI
(S)-2-Amino-3-oxobutanoateGenerator
2-AMINO-3-ketobutyrateGenerator
L-2-Amino-acetoacetic acidGenerator
(2S)-2-amino-3-OxobutanoateHMDB
(2S)-2-amino-3-Oxobutanoic acidHMDB
2-amino-3-OxobutanoateHMDB
2-amino-3-Oxobutanoic acidHMDB
L-2-amino Acetic acidHMDB
Chemical FormulaC4H7NO3
Average Molecular Weight117.1033
Monoisotopic Molecular Weight117.042593095
IUPAC Name(2S)-2-amino-3-oxobutanoic acid
Traditional Name2-amino-3-ketobutyric acid
CAS Registry NumberNot Available
SMILES
CC(=O)[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C4H7NO3/c1-2(6)3(5)4(7)8/h3H,5H2,1H3,(H,7,8)/t3-/m0/s1
InChI KeySAUCHDKDCUROAO-VKHMYHEASA-N
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03915
Phenol Explorer Compound IDNot Available
FooDB IDFDB023915
KNApSAcK IDNot Available
Chemspider ID389046
KEGG Compound IDC03508
BioCyc IDAMINO-OXOBUT
BiGG ID41986
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440033
PDB IDAKB
ChEBI ID40673
Food Biomarker OntologyNot Available
VMH ID2AOBUT
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 5-aminolevulinate synthase, nonspecific, mitochondrial
General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS1
Uniprot ID:
P13196
Molecular weight:
70580.325
Enzyme Details
2. 2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial
General function:
Involved in glycine C-acetyltransferase activity
Specific function:
Not Available
Gene Name:
GCAT
Uniprot ID:
O75600
Molecular weight:
47973.79
Reactions
Acetyl-CoA + Glycine → Coenzyme A + L-2-Amino-3-oxobutanoic aciddetails
Acetyl-CoA + Glycine → Coenzyme A + L-2-Amino-3-oxobutanoic aciddetails