Showing metabocard for 2-Ketobutyric acid (MMDBc0000005)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:13:26 UTC
Update Date2024-10-09 16:41:13 UTC
Metabolite IDMMDBc0000005
Metabolite Identification
Common Name2-Ketobutyric acid
Description2-Ketobutyric acid, also known as alpha-ketobutyrate or 2-oxobutyrate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Ketobutyric acid is a substance that is involved in the metabolism of many amino acids (glycine, methionine, valine, leucine, serine, threonine, isoleucine) as well as propanoate metabolism and C-5 branched dibasic acid metabolism. It is also one of the degradation products of threonine. It can be converted into propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted into succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle. More specifically, 2-ketobutyric acid is a product of the lysis of cystathionine.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb2c0126b0>

      
  Mrv1652309032023492D          

  7  6  0  0  0  0            999 V2000
    2.4602    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7456    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -0.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdb2c0126b0>

HMDB0000005
     RDKit          3D
2-Ketobutyric acid
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.7055   -0.6699    0.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8926    0.4866   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    0.0723   -0.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -0.4456   -1.7421 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6340    0.2367    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5055    0.7589    1.3554 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9003   -0.1376   -0.1660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0786   -1.5747    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302   -0.9681   -0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1732   -0.4066    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4677    0.9348   -1.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8426    1.2620    0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6309    0.4514   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  7 13  1  0
M  END
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3D SDF for #<Metabolite:0x00007fdb2c0126b0>

      
  Mrv1652309032023492D          

  7  6  0  0  0  0            999 V2000
    2.4602    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7456    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -0.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000005

> <DATABASE_NAME>
MIME

> <SMILES>
CCC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)

> <INCHI_KEY>
TYEYBOSBBBHJIV-UHFFFAOYSA-N

> <FORMULA>
C4H6O3

> <MOLECULAR_WEIGHT>
102.0886

> <EXACT_MASS>
102.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.1994455800129

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxobutanoic acid

> <ALOGPS_LOGP>
0.07

> <JCHEM_LOGP>
0.7664098003333332

> <ALOGPS_LOGS>
-0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1869864284881544

> <JCHEM_PKA_STRONGEST_BASIC>
-9.650960797412663

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
22.616600000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.92e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fdb2c0126b0>

HMDB0000005
     RDKit          3D
2-Ketobutyric acid
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.7055   -0.6699    0.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8926    0.4866   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    0.0723   -0.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -0.4456   -1.7421 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6340    0.2367    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5055    0.7589    1.3554 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9003   -0.1376   -0.1660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0786   -1.5747    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302   -0.9681   -0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1732   -0.4066    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4677    0.9348   -1.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8426    1.2620    0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6309    0.4514   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  7 13  1  0
M  END
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PDB for #<Metabolite:0x00007fdb2c0126b0>

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       4.592   0.949   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.258   1.719   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.925   0.949   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.925  -0.591   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.591   1.719   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.742   0.949   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.591   3.259   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for #<Metabolite:0x00007fdb2c0126b0>

COMPND    HMDB0000005
HETATM    1  C1  UNL     1      -1.706  -0.670   0.383  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.893   0.487  -0.163  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.446   0.072  -0.607  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.574  -0.446  -1.742  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.634   0.237   0.214  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.505   0.759   1.355  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.900  -0.138  -0.166  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.079  -1.575   0.546  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.530  -0.968  -0.292  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.173  -0.407   1.366  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.468   0.935  -1.018  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.843   1.262   0.635  1.00  0.00           H  
HETATM   13  H6  UNL     1       3.631   0.451  -0.511  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4    4    5
CONECT    5    6    6    7
CONECT    7   13
END
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SMILES for #<Metabolite:0x00007fdb2c0126b0>

CCC(=O)C(O)=O
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INCHI for #<Metabolite:0x00007fdb2c0126b0>

InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
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Synonyms
ValueSource
2-Ketobutanoic acidChEBI
2-Oxobutyric acidChEBI
3-Methyl pyruvic acidChEBI
alpha-KetobutyrateChEBI
alpha-Ketobutyric acidChEBI
alpha-oxo-N-Butyric acidChEBI
2-OxobutyrateKegg
2-Oxobutanoic acidKegg
2-KetobutanoateGenerator
3-Methyl pyruvateGenerator
a-KetobutyrateGenerator
a-Ketobutyric acidGenerator
Α-ketobutyrateGenerator
Α-ketobutyric acidGenerator
a-oxo-N-ButyrateGenerator
a-oxo-N-Butyric acidGenerator
alpha-oxo-N-ButyrateGenerator
Α-oxo-N-butyrateGenerator
Α-oxo-N-butyric acidGenerator
2-OxobutanoateGenerator
2-KetobutyrateGenerator
2-oxo-ButanoateHMDB
2-oxo-Butanoic acidHMDB
2-oxo-ButyrateHMDB
2-oxo-Butyric acidHMDB
2-oxo-N-ButyrateHMDB
2-oxo-N-Butyric acidHMDB
3-MethylpyruvateHMDB
3-Methylpyruvic acidHMDB
a-Keto-N-butyrateHMDB
a-Keto-N-butyric acidHMDB
a-OxobutyrateHMDB
a-Oxobutyric acidHMDB
alpha-Keto-N-butyrateHMDB
alpha-Keto-N-butyric acidHMDB
alpha-Ketobutric acidHMDB
alpha-OxobutyrateHMDB
alpha-Oxobutyric acidHMDB
Methyl-pyruvateHMDB
Methyl-pyruvic acidHMDB
Propionyl-formateHMDB
Propionyl-formic acidHMDB
alpha-Ketobutyric acid, sodium saltHMDB
2-Ketobutyric acidChEBI
Molecular FormulaC4H6O3
Average Mass102.0886
Monoisotopic Mass102.031694058
IUPAC Name2-oxobutanoic acid
Traditional Name2-oxobutanoic acid
CAS Registry Number600-18-0
SMILES
CCC(=O)C(O)=O
InChI Identifier
InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
InChI KeyTYEYBOSBBBHJIV-UHFFFAOYSA-N