Showing metabocard for 3-carboxy-cis,cis-muconic acid (MMDBc0055352)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 19:49:51 UTC
Update Date2025-10-07 16:09:04 UTC
Metabolite IDMMDBc0055352
Metabolite Identification
Common Name3-carboxy-cis,cis-muconic acid
Description3-carboxy-cis,cis-muconic acid is a dicarboxylic acid and a key intermediate in the catabolism of aromatic compounds, specifically within the biochemical pathways involving the degradation of phenolic compounds. Its chemical structure features two carboxylic acid groups and a conjugated diene system, which contributes to its reactivity and role in various metabolic processes. This compound is generated through the enzymatic conversion of protocatechuic acid (PCA) by certain microbial pathways, notably by the action of protocatechuate 4,5-dioxygenase (PCD), which facilitates the removal of reactive oxygen species (ROS) during this transformation (PMID:31762446 ). The presence of 3-carboxy-cis,cis-muconic acid in metabolic pathways highlights its importance in microbial degradation processes, particularly in the bioremediation of environmental pollutants and the metabolic versatility of certain microorganisms. Its formation and subsequent utilization underscore the interconnectedness of aromatic compound metabolism and the broader implications for ecological and industrial applications.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9aa03ffec0>


  Mrv1652306172221492D          

 16 15  0  0  0  0            999 V2000
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799    1.1994    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  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
 12  7  2  0  0  0  0
 13  7  1  0  0  0  0
 14  1  1  0  0  0  0
 15  2  1  0  0  0  0
 16  3  1  0  0  0  0
M  CHG  3   9  -1  11  -1  13  -1
M  END
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3D MOL for #<Metabolite:0x00007f9aa03ffec0>

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3D SDF for #<Metabolite:0x00007f9aa03ffec0>

  Mrv1652306172221492D          

 16 15  0  0  0  0            999 V2000
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799    1.1994    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  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
 12  7  2  0  0  0  0
 13  7  1  0  0  0  0
 14  1  1  0  0  0  0
 15  2  1  0  0  0  0
 16  3  1  0  0  0  0
M  CHG  3   9  -1  11  -1  13  -1
M  END
> <DATABASE_ID>
MMDBc0055352

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(/[H])\C(=C(\[H])C([O-])=O)\C([O-])=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O6/c8-5(9)2-1-4(7(12)13)3-6(10)11/h1-3H,(H,8,9)(H,10,11)(H,12,13)/p-3/b2-1-,4-3+

> <INCHI_KEY>
KJOVGYUGXHIVAY-BXTBVDPRSA-K

> <FORMULA>
C7H3O6

> <MOLECULAR_WEIGHT>
183.097

> <EXACT_MASS>
182.994608556

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
14.017818202719777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1E,3Z)-buta-1,3-diene-1,2,4-tricarboxylate

> <JCHEM_LOGP>
-0.0786447873333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.8992016949605643

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2693403466082382

> <JCHEM_POLAR_SURFACE_AREA>
120.38999999999999

> <JCHEM_REFRACTIVITY>
73.43610000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-carboxy-cis,cis-muconate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f9aa03ffec0>
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PDB for #<Metabolite:0x00007f9aa03ffec0>
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      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.310   1.334   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -4.620   0.000   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0       0.000   2.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.016   2.239   0.000  0.00  0.00           O-1
HETATM   14  H   UNK     0       0.000  -2.667   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0      -3.080  -2.667   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       2.310   1.334   0.000  0.00  0.00           H+0
CONECT    1    2    4   14                                                  
CONECT    2    1    5   15                                                  
CONECT    3    4    6   16                                                  
CONECT    4    1    3    7                                                  
CONECT    5    2    8    9                                                  
CONECT    6    3   10   11                                                  
CONECT    7    4   12   13                                                  
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    7                                                            
CONECT   14    1                                                            
CONECT   15    2                                                            
CONECT   16    3                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

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3D PDB for #<Metabolite:0x00007f9aa03ffec0>
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SMILES for #<Metabolite:0x00007f9aa03ffec0>
[H]\C(=C(/[H])\C(=C(\[H])C([O-])=O)\C([O-])=O)C([O-])=O
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INCHI for #<Metabolite:0x00007f9aa03ffec0>
InChI=1S/C7H6O6/c8-5(9)2-1-4(7(12)13)3-6(10)11/h1-3H,(H,8,9)(H,10,11)(H,12,13)/p-3/b2-1-,4-3+
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Synonyms
ValueSource
3-Carboxy-cis,cis-muconate trianionChEBI
3-Carboxy-cis,cis-muconic acid trianionGenerator
3-Carboxy-cis,cis-muconic acidGenerator
Molecular FormulaC7H3O6
Average Mass183.097
Monoisotopic Mass182.994608556
IUPAC Name(1E,3Z)-buta-1,3-diene-1,2,4-tricarboxylate
Traditional Name3-carboxy-cis,cis-muconate
CAS Registry NumberNot Available
SMILES
[H]\C(=C(/[H])\C(=C(\[H])C([O-])=O)\C([O-])=O)C([O-])=O
InChI Identifier
InChI=1S/C7H6O6/c8-5(9)2-1-4(7(12)13)3-6(10)11/h1-3H,(H,8,9)(H,10,11)(H,12,13)/p-3/b2-1-,4-3+
InChI KeyKJOVGYUGXHIVAY-BXTBVDPRSA-K