Showing metabocard for 3-chloro-cis,cis-muconic acid (MMDBc0054217)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 22:59:38 UTC
Update Date2025-10-07 16:08:25 UTC
Metabolite IDMMDBc0054217
Metabolite Identification
Common Name3-chloro-cis,cis-muconic acid
Description3-chloro-cis,cis-muconic acid is a chlorinated derivative of muconic acid and belongs to the class of organic compounds known as carboxylic acids. Its chemical structure features a six-carbon backbone with two carboxylic acid groups and a chlorine substituent at the third carbon, with the cis configuration around the double bonds. This compound is involved in microbial degradation pathways, particularly in the breakdown of chlorinated aromatic compounds. For instance, enzyme assays have demonstrated that catechol 1,2-dioxygenase can convert catechol and 4-chlorocatechol into cis,cis-muconic acid and 3-chloro-cis,cis-muconic acid, respectively, indicating its role in the biodegradation process (PMID:14600240 ). Additionally, research has identified an enzyme responsible for the cycloisomerization of 2- and 3-chloro-cis,cis-muconic acid isolated from Pseudomonas sp. grown on 3-chlorobenzoate, further underscoring its significance in microbial metabolic pathways (PMID:7305906 ).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9aa4e47960>

 
  Mrv1533006041517122D          
 
 11 10  0  0  0  0            999 V2000
   16.9632   -9.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9632  -10.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6758   -9.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2507   -9.1415    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.2507  -10.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3921   -9.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5344  -10.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3883  -10.3772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1047   -9.1415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5382   -9.5547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8218  -10.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9aa4e47960>

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3D SDF for #<Metabolite:0x00007f9aa4e47960>
 
  Mrv1533006041517122D          
 
 11 10  0  0  0  0            999 V2000
   16.9632   -9.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9632  -10.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6758   -9.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2507   -9.1415    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.2507  -10.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3921   -9.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5344  -10.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3883  -10.3772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1047   -9.1415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5382   -9.5547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8218  -10.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054217

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)\C=C/C(/Cl)=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H5ClO4/c7-4(3-6(10)11)1-2-5(8)9/h1-3H,(H,8,9)(H,10,11)/b2-1-,4-3+

> <INCHI_KEY>
ICMVYBXQDUXEEE-BXTBVDPRSA-N

> <FORMULA>
C6H5ClO4

> <MOLECULAR_WEIGHT>
176.55

> <EXACT_MASS>
175.9876363

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
14.201514688240945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,4E)-4-chlorohexa-2,4-dienedioic acid

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
0.723064441

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.226480972223682

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.474123571016081

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
39.6418

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-chloro-cis,cis-muconic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f9aa4e47960>
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PDB for #<Metabolite:0x00007f9aa4e47960>
HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      31.665 -17.835   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.665 -19.378   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.995 -17.064   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0      30.335 -17.064   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0      30.335 -20.142   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      34.332 -17.835   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.997 -19.378   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      34.325 -19.371   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      35.662 -17.064   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      29.005 -17.835   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      27.667 -20.149   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1                                                            
CONECT    5    2    7                                                       
CONECT    6    3    8    9                                                  
CONECT    7    5   10   11                                                  
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for #<Metabolite:0x00007f9aa4e47960>
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SMILES for #<Metabolite:0x00007f9aa4e47960>
OC(=O)\C=C/C(/Cl)=C\C(O)=O
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INCHI for #<Metabolite:0x00007f9aa4e47960>
InChI=1S/C6H5ClO4/c7-4(3-6(10)11)1-2-5(8)9/h1-3H,(H,8,9)(H,10,11)/b2-1-,4-3+
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Synonyms
ValueSource
(e,Z)-3-Chloro-2,4-hexadienedioic acidChEBI
3-Chloro-cis,cis-muconateChEBI
(2E,4Z)-3-Chlorohexa-2,4-dienedioateKegg
(e,Z)-3-Chloro-2,4-hexadienedioateGenerator
(2E,4Z)-3-Chlorohexa-2,4-dienedioic acidGenerator
3-chloro-MuconateMeSH
Molecular FormulaC6H5ClO4
Average Mass176.55
Monoisotopic Mass175.9876363
IUPAC Name(2Z,4E)-4-chlorohexa-2,4-dienedioic acid
Traditional Name3-chloro-cis,cis-muconic acid
CAS Registry NumberNot Available
SMILES
OC(=O)\C=C/C(/Cl)=C\C(O)=O
InChI Identifier
InChI=1S/C6H5ClO4/c7-4(3-6(10)11)1-2-5(8)9/h1-3H,(H,8,9)(H,10,11)/b2-1-,4-3+
InChI KeyICMVYBXQDUXEEE-BXTBVDPRSA-N