Showing metabocard for 2-Isopropyl-3-oxosuccinate (MMDBc0029916)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:46:44 UTC
Update Date2022-08-31 17:37:36 UTC
Metabolite IDMMDBc0029916
Metabolite Identification
Common Name2-Isopropyl-3-oxosuccinate
Description2-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 to 4-Methyl-2-oxopentanoate via spontaneous reaction.(BioCyc)
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fecadb8ac08>


  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
Download

3D MOL for #<Metabolite:0x00007fecadb8ac08>

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
Download

3D SDF for #<Metabolite:0x00007fecadb8ac08>


  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>
MMDBc0029916

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007fecadb8ac08>

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
Download

PDB for #<Metabolite:0x00007fecadb8ac08>

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 #<Metabolite:0x00007fecadb8ac08>

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 #<Metabolite:0x00007fecadb8ac08>

CC(C)[C@H](C(O)=O)C(=O)C(O)=O
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INCHI for #<Metabolite:0x00007fecadb8ac08>

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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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
Molecular FormulaC7H10O5
Average Mass174.1513
Monoisotopic Mass174.05282343
IUPAC Name(3S)-2-oxo-3-(propan-2-yl)butanedioic acid
Traditional Name(2S)-2-isopropyl-3-oxobutanedioic acid
CAS Registry NumberNot Available
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