Showing metabocard for 3-oxoadipate (MMDBc0055404)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 19:51:15 UTC
Update Date2025-10-07 16:09:06 UTC
Metabolite IDMMDBc0055404
Metabolite Identification
Common Name3-oxoadipate
Description3-oxoadipate is a dicarboxylic acid derivative belonging to the chemical class of keto acids. It is characterized by a six-carbon backbone with two carboxyl groups and a ketone functional group, which plays a crucial role in various metabolic pathways. In microbial metabolism, 3-oxoadipate is an intermediate in the degradation of aromatic compounds, particularly in the ortho- and meta-cleavage pathways. For instance, it is formed during the conversion of 3-chlorocatechol, which is derived from 3-chlorobenzoate, as detailed in the literature (PMID:38488372 ). Additionally, it participates in the metabolic engineering of strains to enhance the shikimate and β-ketoadipic acid pathways, where the 3-oxoadipate CoA-transferase gene is often targeted to prevent the loss of biosynthetic intermediates (PMID:39343057 ). The yeast Candida parapsilosis utilizes both the 3-oxoadipate and gentisate pathways, with specific gene clusters encoding the necessary enzymes and transporters that are upregulated in a substrate-specific manner (PMID:35255079 ). Furthermore, the detection of 3-oxoadipate indicates the coexistence of dual metabolic pathways for phenol degradation in certain strains (PMID:37651933 ).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9ac47e36a8>


  Mrv1652306172221512D          

 11 10  0  0  0  0            999 V2000
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  6  1  0  0  0  0
M  CHG  2   9  -1  11  -1
M  END
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3D MOL for #<Metabolite:0x00007f9ac47e36a8>

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3D SDF for #<Metabolite:0x00007f9ac47e36a8>

  Mrv1652306172221512D          

 11 10  0  0  0  0            999 V2000
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  6  1  0  0  0  0
M  CHG  2   9  -1  11  -1
M  END
> <DATABASE_ID>
MMDBc0055404

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O5/c7-4(3-6(10)11)1-2-5(8)9/h1-3H2,(H,8,9)(H,10,11)/p-2

> <INCHI_KEY>
RTGHRDFWYQHVFW-UHFFFAOYSA-L

> <FORMULA>
C6H6O5

> <MOLECULAR_WEIGHT>
158.11

> <EXACT_MASS>
158.022620453

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.2508358903325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxohexanedioate

> <JCHEM_LOGP>
-0.1766289986666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.235829200342627

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4748505038613806

> <JCHEM_PKA_STRONGEST_BASIC>
-7.5471659957939785

> <JCHEM_POLAR_SURFACE_AREA>
97.33

> <JCHEM_REFRACTIVITY>
55.1064

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
β-ketoadipate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f9ac47e36a8>
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PDB for #<Metabolite:0x00007f9ac47e36a8>
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       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.287   1.127   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.953   2.667   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.286   4.977   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O-1
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    4    6                                                       
CONECT    4    1    3    7                                                  
CONECT    5    2    8    9                                                  
CONECT    6    3   10   11                                                  
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for #<Metabolite:0x00007f9ac47e36a8>
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SMILES for #<Metabolite:0x00007f9ac47e36a8>
[O-]C(=O)CCC(=O)CC([O-])=O
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INCHI for #<Metabolite:0x00007f9ac47e36a8>
InChI=1S/C6H8O5/c7-4(3-6(10)11)1-2-5(8)9/h1-3H2,(H,8,9)(H,10,11)/p-2
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Synonyms
ValueSource
3-Keto-adipateChEBI
3-Keto-adipic acidGenerator
3-Oxoadipic acidGenerator
Molecular FormulaC6H6O5
Average Mass158.11
Monoisotopic Mass158.022620453
IUPAC Name3-oxohexanedioate
Traditional Nameβ-ketoadipate
CAS Registry NumberNot Available
SMILES
[O-]C(=O)CCC(=O)CC([O-])=O
InChI Identifier
InChI=1S/C6H8O5/c7-4(3-6(10)11)1-2-5(8)9/h1-3H2,(H,8,9)(H,10,11)/p-2
InChI KeyRTGHRDFWYQHVFW-UHFFFAOYSA-L