Showing metabocard for 4-hydroxy-4-methyl-2-oxoglutarate (MMDBc0055487)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 19:54:48 UTC
Update Date2025-10-07 16:09:09 UTC
Metabolite IDMMDBc0055487
Metabolite Identification
Common Name4-hydroxy-4-methyl-2-oxoglutarate
Description4-hydroxy-4-methyl-2-oxoglutarate is a metabolite classified within the chemical class of oxoglutarates. Its chemical structure features a hydroxyl group and a methyl group attached to the 4-position of a 2-oxoglutarate backbone, which is pivotal in various biochemical pathways. This compound is notably involved in the catabolism of aromatic compounds, specifically functioning as a substrate for the enzyme 4-hydroxy-4-methyl-2-oxoglutarate aldolase, which catalyzes the final step of the gallate and protocatechuate 4,5-cleavage pathways, linking aromatic degradation to central metabolism (PMID:27741265 ). Additionally, it plays a role in regulatory networks, with genes such as UDP-glycosyltransferase and 4-hydroxy-4-methyl-2-oxoglutarate aldolase being correlated with quantitative traits in various organisms (PMID:35991419 ). The enzyme itself is classified as a class II aldolase, dependent on divalent metal ions, and exhibits structural and kinetic characteristics that underscore its evolutionary significance in metabolic pathways (PMID:24359411 ). Overall, 4-hydroxy-4-methyl-2-oxoglutarate serves as a crucial intermediate in microbial metabolism and enzymatic reactions.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fae027df250>


  Mrv1652306172221542D          

 12 11  0  0  0  0            999 V2000
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   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
   -0.6039    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.4750    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.8250    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  5  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
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
M  CHG  2   8  -1  11  -1
M  END
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3D MOL for #<Metabolite:0x00007fae027df250>

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3D SDF for #<Metabolite:0x00007fae027df250>

  Mrv1652306172221542D          

 12 11  0  0  0  0            999 V2000
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   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
   -0.6039    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.4750    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.8250    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  5  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
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
M  CHG  2   8  -1  11  -1
M  END
> <DATABASE_ID>
MMDBc0055487

> <DATABASE_NAME>
MIME

> <SMILES>
CC(O)(CC(=O)C([O-])=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O6/c1-6(12,5(10)11)2-3(7)4(8)9/h12H,2H2,1H3,(H,8,9)(H,10,11)/p-2

> <INCHI_KEY>
YRWAMSXHYBBHFL-UHFFFAOYSA-L

> <FORMULA>
C6H6O6

> <MOLECULAR_WEIGHT>
174.109

> <EXACT_MASS>
174.017535073

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.826303157528585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-2-methyl-4-oxopentanedioate

> <JCHEM_LOGP>
-0.3916558743333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.457350902943283

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6071830196248458

> <JCHEM_PKA_STRONGEST_BASIC>
-3.941142775616501

> <JCHEM_POLAR_SURFACE_AREA>
117.56000000000002

> <JCHEM_REFRACTIVITY>
56.608700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-2-methyl-4-oxopentanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fae027df250>
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PDB for #<Metabolite:0x00007fae027df250>
HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.206   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.206   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.127   1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.127   4.620   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0       1.540   4.620   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.206  -2.310   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    6                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    8    9                                                  
CONECT    5    6   10   11                                                  
CONECT    6    1    2    5   12                                             
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for #<Metabolite:0x00007fae027df250>
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SMILES for #<Metabolite:0x00007fae027df250>
CC(O)(CC(=O)C([O-])=O)C([O-])=O
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INCHI for #<Metabolite:0x00007fae027df250>
InChI=1S/C6H8O6/c1-6(12,5(10)11)2-3(7)4(8)9/h12H,2H2,1H3,(H,8,9)(H,10,11)/p-2
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Synonyms
ValueSource
4-Hydroxy-4-methyl-2-oxoglutarate dianionChEBI
4-Hydroxy-4-methyl-2-oxoglutaric acid dianionGenerator
4-Hydroxy-4-methyl-2-oxoglutaric acidGenerator
Molecular FormulaC6H6O6
Average Mass174.109
Monoisotopic Mass174.017535073
IUPAC Name2-hydroxy-2-methyl-4-oxopentanedioate
Traditional Name2-hydroxy-2-methyl-4-oxopentanedioate
CAS Registry NumberNot Available
SMILES
CC(O)(CC(=O)C([O-])=O)C([O-])=O
InChI Identifier
InChI=1S/C6H8O6/c1-6(12,5(10)11)2-3(7)4(8)9/h12H,2H2,1H3,(H,8,9)(H,10,11)/p-2
InChI KeyYRWAMSXHYBBHFL-UHFFFAOYSA-L