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Showing metabocard for 2-Isopropyl-3-oxosuccinate (HMDB0012149)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:02 UTC
Update Date2023-02-21 17:17:40 UTC
HMDB IDHMDB0012149
Secondary Accession Numbers
  • HMDB12149
Metabolite Identification
Common Name2-Isopropyl-3-oxosuccinate
Description2-Isopropyl-3-oxosuccinate belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain that contains less than 6 carbon atoms. 2-Isopropyl-3-oxosuccinate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Isopropyl-3-oxosuccinate exists in all living species, ranging from bacteria to humans. 2-Isopropyl-3-oxosuccinate has been detected, but not quantified in, several different foods, such as garden onion (var.), German camomiles, limes, cloud ear fungus, and citrus. This could make 2-isopropyl-3-oxosuccinate a potential biomarker for the consumption of these foods. 2-Isopropyl-3-oxosuccinate is an intermediate in leucine biosynthesis and can be generated from (2R,3S)-3-isopropylmalate. It is the third step in leucine biosynthesis after the fork from valine synthesis. It is an oxidative decarboxylation. Leucine biosynthesis involves a five-step conversion process starting with the valine precursor 2-keto-isovalerate. The final step in this pathway is catalyzed by two transaminases of broad specificity: branched-chain amino acid transferase (IlvE) and tyrosine aminotransferase (TyrB). In this pathway, 2-isopropyl-3-oxosuccinate is converted into 4-methyl-2-oxopentanoate via a spontaneous reaction (BioCyc).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012149 (2-Isopropyl-3-oxosuccinate)

  Mrv1652309042000342D          

 12 11  0  0  0  0            999 V2000
   -0.7810    0.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4955   -0.2232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7810    1.0142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0665   -0.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0665   -1.0482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    0.1892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6478    1.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0665    1.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623    1.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623   -0.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623   -1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    0.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  4  5  2  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
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3D MOL for HMDB0012149 (2-Isopropyl-3-oxosuccinate)

HMDB0012149
     RDKit          3D
2-Isopropyl-3-oxosuccinate
 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.6772    0.6107   -0.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799   -0.2393    0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253   -1.6941   -0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1227   -0.0837    0.6769 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3703    1.3031    1.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7253    1.6210    2.2668 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087    2.3317    0.1853 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611   -0.4897   -0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533   -0.9513   -1.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5520   -0.3572    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8826    0.1014    1.2963 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6208   -0.7147   -0.6657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833    0.5583   -1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6576    0.2254   -1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8896    1.6679   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9526   -0.0098    1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211   -2.3192    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766   -2.0773    0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401   -1.8705   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334   -0.7230    1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2639    3.1688    0.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1370   -0.0585   -1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  7 21  1  0
 12 22  1  0
M  END
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3D SDF for HMDB0012149 (2-Isopropyl-3-oxosuccinate)

  Mrv1652309042000342D          

 12 11  0  0  0  0            999 V2000
   -0.7810    0.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4955   -0.2232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7810    1.0142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0665   -0.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0665   -1.0482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    0.1892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6478    1.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0665    1.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623    1.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623   -0.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623   -1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    0.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  4  5  2  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012149

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H10O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-4H,1-2H3,(H,9,10)(H,11,12)/t4-/m0/s1

> <INCHI_KEY>
HIIZAGQWABAMRR-BYPYZUCNSA-N

> <FORMULA>
C7H10O5

> <MOLECULAR_WEIGHT>
174.1513

> <EXACT_MASS>
174.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.82669184112504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-2-oxo-3-(propan-2-yl)butanedioic acid

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
1.2326764389999998

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.030518812521971

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.933653579611946

> <JCHEM_PKA_STRONGEST_BASIC>
-9.953657597776589

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
38.057900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-isopropyl-3-oxobutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0012149 (2-Isopropyl-3-oxosuccinate)

HMDB0012149
     RDKit          3D
2-Isopropyl-3-oxosuccinate
 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.6772    0.6107   -0.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799   -0.2393    0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253   -1.6941   -0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1227   -0.0837    0.6769 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3703    1.3031    1.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7253    1.6210    2.2668 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087    2.3317    0.1853 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611   -0.4897   -0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533   -0.9513   -1.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5520   -0.3572    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8826    0.1014    1.2963 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6208   -0.7147   -0.6657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833    0.5583   -1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6576    0.2254   -1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8896    1.6679   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9526   -0.0098    1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211   -2.3192    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766   -2.0773    0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401   -1.8705   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334   -0.7230    1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2639    3.1688    0.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1370   -0.0585   -1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  7 21  1  0
 12 22  1  0
M  END
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PDB for HMDB0012149 (2-Isopropyl-3-oxosuccinate)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.458   0.353   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.792  -0.417   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -1.458   1.893   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.124  -0.417   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.124  -1.957   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.209   0.353   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.209   1.893   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.124   2.663   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.543   2.663   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.543  -0.417   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.543  -1.957   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.877   0.353   0.000  0.00  0.00           C+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    6    5                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for HMDB0012149 (2-Isopropyl-3-oxosuccinate)

COMPND    HMDB0012149
HETATM    1  C1  UNL     1      -1.677   0.611  -0.939  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.280  -0.239   0.211  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.525  -1.694  -0.141  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.123  -0.084   0.677  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.370   1.303   1.103  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.725   1.621   2.267  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.209   2.332   0.185  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.161  -0.490  -0.259  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.953  -0.951  -1.405  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.552  -0.357   0.150  1.00  0.00           C  
HETATM   11  O4  UNL     1       2.883   0.101   1.296  1.00  0.00           O  
HETATM   12  O5  UNL     1       3.621  -0.715  -0.666  1.00  0.00           O  
HETATM   13  H1  UNL     1      -0.983   0.558  -1.799  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.658   0.225  -1.323  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.890   1.668  -0.635  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.953  -0.010   1.064  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.721  -2.319   0.289  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.477  -2.077   0.275  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.540  -1.871  -1.235  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.233  -0.723   1.599  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.264   3.169   0.523  1.00  0.00           H  
HETATM   22  H10 UNL     1       4.137  -0.059  -1.237  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   16
CONECT    3   17   18   19
CONECT    4    5    8   20
CONECT    5    6    6    7
CONECT    7   21
CONECT    8    9    9   10
CONECT   10   11   11   12
CONECT   12   22
END
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SMILES for HMDB0012149 (2-Isopropyl-3-oxosuccinate)

CC(C)[C@H](C(O)=O)C(=O)C(O)=O
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INCHI for HMDB0012149 (2-Isopropyl-3-oxosuccinate)

InChI=1S/C7H10O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-4H,1-2H3,(H,9,10)(H,11,12)/t4-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(2S)-2-(1-Methylethyl)-3-oxobutanedioic acidChEBI
(2S)-2-Isopropyl-3-oxosuccinateChEBI
3-Carboxy-4-methyl-2-oxopentanoateChEBI
2-oxo-4-Methyl-3-carboxypentanoateKegg
(2S)-2-(1-Methylethyl)-3-oxobutanedioateGenerator
(2S)-2-Isopropyl-3-oxosuccinic acidGenerator
3-Carboxy-4-methyl-2-oxopentanoic acidGenerator
2-oxo-4-Methyl-3-carboxypentanoic acidGenerator
2-Isopropyl-3-oxosuccinic acidGenerator
(2S)-3-oxo-2-(Propan-2-yl)butanedioateHMDB
(2S)-3-oxo-2-(Propan-2-yl)butanedioic acidHMDB
2-(1-Methylethyl)-3-oxobutanedioic acidHMDB
2-Oxo-3-isopropylsuccinic acidHMDB
Chemical FormulaC7H10O5
Average Molecular Weight174.1513
Monoisotopic Molecular Weight174.05282343
IUPAC Name(3S)-2-oxo-3-(propan-2-yl)butanedioic acid
Traditional Name(2S)-2-isopropyl-3-oxobutanedioic acid
CAS Registry Number1245945-28-1
SMILES
CC(C)[C@H](C(O)=O)C(=O)C(O)=O
InChI Identifier
InChI=1S/C7H10O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-4H,1-2H3,(H,9,10)(H,11,12)/t4-/m0/s1
InChI KeyHIIZAGQWABAMRR-BYPYZUCNSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Beta-keto acid
  • Branched fatty acid
  • Short-chain keto acid
  • Methyl-branched fatty acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Fatty acyl
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
Process
Naturally occurring process
RoleNot Available
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 LocationsNot Available
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028806
KNApSAcK IDNot Available
Chemspider ID4575347
KEGG Compound IDC04236
BioCyc IDCPD-7100
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5462259
PDB IDNot Available
ChEBI ID1467
Food Biomarker OntologyNot Available
VMH ID3C4MOP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available