Showing metabocard for cis,cis-Muconic acid (MMDBc0047950)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:18:20 UTC
Update Date2022-09-01 02:02:45 UTC
Metabolite IDMMDBc0047950
Metabolite Identification
Common Namecis,cis-Muconic acid
Descriptioncis-cis-Muconic acid is a presumptive metabolite of benzene. Muconic acid was first isolated from the urine of rabbits and dogs in 1909 (M. Jaffe, Z Physiol Chem 62:58-67). It was originally thought that if muconic acid was formed by the opening of the benzene ring in vivo then the cis-cis isomer should be the initial (and primary) product. However subsequent studies conducted in the 1950s proved that trans-trans-muconic acid is a true metabolite of benzene in mammals (Parke DV, Williams RT. Biochem J 51:339-348 (1952)). Furthermore, dosing rabbits with phenol or catechol also resulted in the urinary excretion of trans-trans-muconic acid. The oxidative ring opening of benzene first gives rise to cis-cis-muconaldehyde, which then isomerizes to cis-trans- and trans-trans-muconaldehyde; the latter is oxidized in vivo to trans-trans-muconic acid. Isomerization of the trans-trans form may take place in vivo to yield small amounts if the cis-cis and cis-trans form of muconic acid. cis-cis-Muconic acid may also be generated from microbial fermentation of benzoic acid. Certain strains of arthobacter are particularly efficient at this process. cis-cis-Muconic acid can also be found in Pseudomonas and Escherichia coli (https://link.springer.com/article/10.1007/BF00250491) (PMID:26360870 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f1218160ef0>


  Mrv1652305271900062D          

 10  9  0  0  0  0            999 V2000
 9993.2135 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9277 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7546 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4682 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1837 9993.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4682 9992.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3880 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6733 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9586 9993.3504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6733 9994.5873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f1218160ef0>

HMDB0006331
     RDKit          3D
cis,cis-Muconic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.0259   -2.0091   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -0.8240   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7536   -0.5880   -0.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.3671   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2518    0.4136    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -0.7871    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8343   -0.7499    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072    0.4245    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.2333    0.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    1.7439    0.3501 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1866    0.0990    0.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0728    1.3710   -0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.4201    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -1.7840    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3584   -1.7469    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4442    2.4164   -0.3844 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
 10 16  1  0
M  END
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3D SDF for #<Metabolite:0x00007f1218160ef0>


  Mrv1652305271900062D          

 10  9  0  0  0  0            999 V2000
 9993.2135 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9277 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7546 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4682 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1837 9993.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4682 9992.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3880 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6733 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9586 9993.3504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6733 9994.5873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047950

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1-,4-2-

> <INCHI_KEY>
TXXHDPDFNKHHGW-CCAGOZQPSA-N

> <FORMULA>
C6H6O4

> <MOLECULAR_WEIGHT>
142.1094

> <EXACT_MASS>
142.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.537125034306658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
0.486301342

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.654855678562283

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.87177055186766

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
34.925599999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
muconic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f1218160ef0>

HMDB0006331
     RDKit          3D
cis,cis-Muconic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.0259   -2.0091   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -0.8240   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7536   -0.5880   -0.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.3671   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2518    0.4136    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -0.7871    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8343   -0.7499    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072    0.4245    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.2333    0.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    1.7439    0.3501 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1866    0.0990    0.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0728    1.3710   -0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.4201    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -1.7840    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3584   -1.7469    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4442    2.4164   -0.3844 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
 10 16  1  0
M  END
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PDB for #<Metabolite:0x00007f1218160ef0>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8653.9998654.254   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8655.3328655.023   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8656.8758655.023   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8658.2078654.254   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8659.5438655.023   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8658.2078652.713   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8652.4588654.254   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8651.1238655.023   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8649.7898654.254   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8651.1238656.563   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x00007f1218160ef0>

COMPND    HMDB0006331
HETATM    1  O1  UNL     1       2.026  -2.009  -0.139  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.344  -0.824  -0.117  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.754  -0.588  -0.218  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.567   0.367  -0.008  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.252   0.414   0.098  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.523  -0.787   0.111  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.834  -0.750   0.215  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.607   0.425   0.323  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.897   0.233   0.417  1.00  0.00           O  
HETATM   10  O4  UNL     1      -2.280   1.744   0.350  1.00  0.00           O  
HETATM   11  H1  UNL     1       4.187   0.099   0.366  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.073   1.371  -0.008  1.00  0.00           H  
HETATM   13  H3  UNL     1      -0.219   1.420   0.175  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.040  -1.784   0.033  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.358  -1.747   0.217  1.00  0.00           H  
HETATM   16  H6  UNL     1      -2.444   2.416  -0.384  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    5   12
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7    8   15
CONECT    8    9    9   10
CONECT   10   16
END
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SMILES for #<Metabolite:0x00007f1218160ef0>

OC(=O)\C=C/C=C\C(O)=O
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INCHI for #<Metabolite:0x00007f1218160ef0>

InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1-,4-2-
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Synonyms
ValueSource
(2Z,4Z)-HEXA-2,4-dienedioIC ACIDChEBI
(Z,Z)-2,4-Hexadienedioic acidChEBI
cis,cis-2,4-Hexadienedioic acidChEBI
cis,cis-HexadienedioateKegg
(2Z,4Z)-HEXA-2,4-dienedioateGenerator
(Z,Z)-2,4-HexadienedioateGenerator
cis,cis-2,4-HexadienedioateGenerator
cis,cis-Hexadienedioic acidGenerator
cis,cis-MuconateGenerator
trans-trans-MuconateHMDB
2,4-HexadienedioateHMDB
2,4-Hexadienedioic acidHMDB
Muconic acidHMDB
Muconic acid, (e,e)-isomerHMDB
trans-beta-Hydromuconic acidHMDB
trans,trans-Muconic acidHMDB
Molecular FormulaC6H6O4
Average Mass142.1094
Monoisotopic Mass142.02660868
IUPAC Name(2Z,4Z)-hexa-2,4-dienedioic acid
Traditional Namemuconic acid
CAS Registry Number1119-72-8
SMILES
OC(=O)\C=C/C=C\C(O)=O
InChI Identifier
InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1-,4-2-
InChI KeyTXXHDPDFNKHHGW-CCAGOZQPSA-N