Showing metabocard for 3-hydroxy-cis,cis-muconic acid (MMDBc0054226)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 23:00:09 UTC
Update Date2025-10-07 16:08:25 UTC
Metabolite IDMMDBc0054226
Metabolite Identification
Common Name3-hydroxy-cis,cis-muconic acid
Description3-hydroxy-cis,cis-muconic acid is a dicarboxylic acid and a member of the class of organic compounds known as muconic acids. Its chemical structure features a hydroxyl group and two carboxylic acid groups, contributing to its reactivity and participation in various biochemical pathways. This compound is generated through the ozonolysis of specific hydroxybenzenes, such as 1,2,3- and 1,2,4-trihydroxybenezene, leading to the formation of 2- and 3-hydroxy-cis,cis-muconic acid, respectively (PMID:26403273 ). Furthermore, 3-hydroxy-cis,cis-muconic acid is involved in metabolic pathways where it can be further processed into other dicarboxylic acids, such as 2,4- or 3,4-dihydroxyhex-2-enedioic acid, indicating its role in the degradation and transformation of aromatic compounds (PMID:26403273 ). This underscores its importance in the context of microbial metabolism and environmental biochemistry, where it may serve as an intermediate in the catabolism of aromatic pollutants.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9ad05c83d0>

 
  Mrv1533006041517302D          
 
 11 10  0  0  0  0            999 V2000
   10.8220   -8.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8220   -9.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5345   -7.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1094   -7.7813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1094   -9.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2508   -8.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3931   -9.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2470   -9.2643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9634   -7.8638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6805   -9.5163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3969   -8.3182    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:0x00007f9ad05c83d0>

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3D SDF for #<Metabolite:0x00007f9ad05c83d0>
 
  Mrv1533006041517302D          
 
 11 10  0  0  0  0            999 V2000
   10.8220   -8.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8220   -9.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5345   -7.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1094   -7.7813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1094   -9.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2508   -8.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3931   -9.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2470   -9.2643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9634   -7.8638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6805   -9.5163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3969   -8.3182    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>
MMDBc0054226

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O5/c7-4(3-6(10)11)1-2-5(8)9/h1-3,7H,(H,8,9)(H,10,11)/b2-1-,4-3+

> <INCHI_KEY>
DLKZGMNZEDNHKO-BXTBVDPRSA-N

> <FORMULA>
C6H6O5

> <MOLECULAR_WEIGHT>
158.109

> <EXACT_MASS>
158.021523293

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.066904424565717

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.03

> <JCHEM_LOGP>
-0.18454555700000005

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.387391383655183

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.621741867680603

> <JCHEM_PKA_STRONGEST_BASIC>
-6.5285863834849005

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
36.817899999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.88e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f9ad05c83d0>
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PDB for #<Metabolite:0x00007f9ad05c83d0>
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      20.201 -15.450   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.201 -16.993   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.531 -14.679   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      18.871 -14.525   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      18.871 -17.757   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.868 -15.450   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.534 -16.993   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      22.861 -17.293   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      24.198 -14.679   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      16.204 -17.764   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      17.541 -15.527   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:0x00007f9ad05c83d0>
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SMILES for #<Metabolite:0x00007f9ad05c83d0>
OC(=O)\C=C/C(/O)=C\C(O)=O
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INCHI for #<Metabolite:0x00007f9ad05c83d0>
InChI=1S/C6H6O5/c7-4(3-6(10)11)1-2-5(8)9/h1-3,7H,(H,8,9)(H,10,11)/b2-1-,4-3+
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Synonyms
ValueSource
3-Hydroxy-cis,cis-muconateChEBI
Molecular FormulaC6H6O5
Average Mass158.109
Monoisotopic Mass158.021523293
IUPAC Name(2Z,4E)-4-hydroxyhexa-2,4-dienedioic acid
Traditional Name3-hydroxy-cis,cis-muconate
CAS Registry NumberNot Available
SMILES
OC(=O)\C=C/C(/O)=C\C(O)=O
InChI Identifier
InChI=1S/C6H6O5/c7-4(3-6(10)11)1-2-5(8)9/h1-3,7H,(H,8,9)(H,10,11)/b2-1-,4-3+
InChI KeyDLKZGMNZEDNHKO-BXTBVDPRSA-N