Showing metabocard for 4-Hydroxy-2-oxoglutaric acid (MMDBc0029681)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:37:19 UTC
Update Date2022-08-31 17:11:57 UTC
Metabolite IDMMDBc0029681
Metabolite Identification
Common Name4-Hydroxy-2-oxoglutaric acid
Description4-hydroxy-2-oxoglutaric acid is a member of the chemical class known as Gamma Keto-Acids and Derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. 4-hydroxy-2-oxoglutaric acid is invovled in Glyoxylate and dicarboxylate metabolism. 2-Keto-4-hydroxyglutarate aldolase also plays a role in respiratory metabolic pathways, which suggests a mechanism for respiration resumption during the termination of the SOS response. (PMID 8524853 )
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f92397b5890>


  Mrv0541 02231219212D          

 11 10  0  0  0  0            999 V2000
   25.4195   -5.5109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9905   -4.6859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2774   -4.6859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7050   -3.4483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5630   -3.4483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8484   -5.5109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4195   -4.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1340   -4.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7050   -4.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5630   -4.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8484   -4.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  2  0  0  0  0
  6 11  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f92397b5890>

HMDB0002070
     RDKit          3D
4-Hydroxy-2-oxoglutaric acid
 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.5276   -1.7368    0.5703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -0.4988    0.4399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8032    0.1308    0.4236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3662    0.2609    0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4324    1.5051    0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0407   -0.3985    0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0412    0.6541    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037    1.2774   -1.0572 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892    0.0498    0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0773    0.1648   -0.9187 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9432   -0.6524    1.1744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0044    0.8916   -0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375   -1.0574   -0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1164   -1.0284    1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    1.3991    0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0324    0.6134   -1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290   -1.5749    1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  3 12  1  0
  6 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
 11 17  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f92397b5890>


  Mrv0541 02231219212D          

 11 10  0  0  0  0            999 V2000
   25.4195   -5.5109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9905   -4.6859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2774   -4.6859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7050   -3.4483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5630   -3.4483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8484   -5.5109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4195   -4.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1340   -4.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7050   -4.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5630   -4.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8484   -4.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  2  0  0  0  0
  6 11  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029681

> <DATABASE_NAME>
MIME

> <SMILES>
OC(CC(=O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O6/c6-2(4(8)9)1-3(7)5(10)11/h2,6H,1H2,(H,8,9)(H,10,11)

> <INCHI_KEY>
WXSKVKPSMAHCSG-UHFFFAOYSA-N

> <FORMULA>
C5H6O6

> <MOLECULAR_WEIGHT>
162.0975

> <EXACT_MASS>
162.016437924

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
12.76221872205969

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-4-oxopentanedioic acid

> <ALOGPS_LOGP>
-1.11

> <JCHEM_LOGP>
-0.8244217603333331

> <ALOGPS_LOGS>
-0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.33119390093207

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.449105918946765

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8864249286801433

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999998

> <JCHEM_REFRACTIVITY>
30.221199999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.98e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-2-oxoglutaric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f92397b5890>

HMDB0002070
     RDKit          3D
4-Hydroxy-2-oxoglutaric acid
 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.5276   -1.7368    0.5703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -0.4988    0.4399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8032    0.1308    0.4236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3662    0.2609    0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4324    1.5051    0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0407   -0.3985    0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0412    0.6541    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037    1.2774   -1.0572 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892    0.0498    0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0773    0.1648   -0.9187 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9432   -0.6524    1.1744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0044    0.8916   -0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375   -1.0574   -0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1164   -1.0284    1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    1.3991    0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0324    0.6134   -1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290   -1.5749    1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  3 12  1  0
  6 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
 11 17  1  0
M  END
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PDB for #<Metabolite:0x00007f92397b5890>

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  O   UNK     0      47.450 -10.287   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      44.782  -8.747   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      52.784  -8.747   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      46.116  -6.437   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      51.451  -6.437   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      50.117 -10.287   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      47.450  -8.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      48.783  -7.977   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      46.116  -7.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      51.451  -7.977   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      50.117  -8.747   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    9                                                            
CONECT    5   10                                                            
CONECT    6   11                                                            
CONECT    7    1    8    9                                                  
CONECT    8    7   11                                                       
CONECT    9    2    4    7                                                  
CONECT   10    3    5   11                                                  
CONECT   11    6    8   10                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for #<Metabolite:0x00007f92397b5890>

COMPND    HMDB0002070
HETATM    1  O1  UNL     1      -2.528  -1.737   0.570  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.583  -0.499   0.440  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.803   0.131   0.424  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.366   0.261   0.307  1.00  0.00           C  
HETATM    5  O3  UNL     1      -1.432   1.505   0.176  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.041  -0.398   0.322  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.041   0.654   0.164  1.00  0.00           C  
HETATM    8  O4  UNL     1       0.804   1.277  -1.057  1.00  0.00           O  
HETATM    9  C5  UNL     1       2.389   0.050   0.114  1.00  0.00           C  
HETATM   10  O5  UNL     1       3.077   0.165  -0.919  1.00  0.00           O  
HETATM   11  O6  UNL     1       2.943  -0.652   1.174  1.00  0.00           O  
HETATM   12  H1  UNL     1      -4.004   0.892  -0.216  1.00  0.00           H  
HETATM   13  H2  UNL     1       0.037  -1.057  -0.581  1.00  0.00           H  
HETATM   14  H3  UNL     1       0.116  -1.028   1.221  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.988   1.399   0.996  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.032   0.613  -1.768  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.329  -1.575   1.090  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5    6
CONECT    6    7   13   14
CONECT    7    8    9   15
CONECT    8   16
CONECT    9   10   10   11
CONECT   11   17
END
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SMILES for #<Metabolite:0x00007f92397b5890>

OC(CC(=O)C(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007f92397b5890>

InChI=1S/C5H6O6/c6-2(4(8)9)1-3(7)5(10)11/h2,6H,1H2,(H,8,9)(H,10,11)
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Synonyms
ValueSource
4-Hydroxy-2-oxoglutarateGenerator
2-Keto-4-hydroxyglutarateMeSH
2-Keto-4-hydroxyglutarate, (+-)-isomerMeSH
(+/-)-2-hydroxy-4-oxopentanedioateHMDB
(+/-)-2-hydroxy-4-oxopentanedioic acidHMDB
2-Hydroxy-4-oxopentanedioateHMDB
2-Hydroxy-4-oxopentanedioic acidHMDB
2-oxo-4-HydroxyglutarateHMDB
4-Hydroxy-2-ketoglutarateHMDB
D-4-Hydroxy-2-ketoglutarateHMDB
Molecular FormulaC5H6O6
Average Mass162.0975
Monoisotopic Mass162.016437924
IUPAC Name2-hydroxy-4-oxopentanedioic acid
Traditional Name4-hydroxy-2-oxoglutaric acid
CAS Registry NumberNot Available
SMILES
OC(CC(=O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H6O6/c6-2(4(8)9)1-3(7)5(10)11/h2,6H,1H2,(H,8,9)(H,10,11)
InChI KeyWXSKVKPSMAHCSG-UHFFFAOYSA-N