Showing metabocard for 2-hydroxy-5-methylquinone (MMDBc0055238)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 19:47:01 UTC
Update Date2025-10-07 16:09:02 UTC
Metabolite IDMMDBc0055238
Metabolite Identification
Common Name2-hydroxy-5-methylquinone
Description2-hydroxy-5-methylquinone is a quinone, specifically a substituted derivative of quinone, characterized by the presence of a hydroxyl group at the 2-position and a methyl group at the 5-position of the quinone ring. Its chemical structure features a six-membered aromatic ring with alternating double bonds, typical of quinones, and additional functional groups that enhance its reactivity. This compound plays a role in various biochemical pathways, particularly in the degradation of nitroaromatic compounds. For instance, strain DNT catalyzes the conversion of 4M5NC to 2-hydroxy-5-methylquinone, facilitating the removal of the nitro group during the degradation of 2,4-dinitrotoluene (PMID:16751499 ). Additionally, it is produced through the activity of enzymes such as DntB or MNC monooxygenase, which metabolize 4M5NC and MNC, respectively, in the presence of NADPH and oxygen (PMIDs:12801097, 8830701). The identification of 2-hydroxy-5-methylquinone has been confirmed using gas chromatography-mass spectrometry, highlighting its significance in environmental and microbial biochemistry (PMID:8195105 ).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f2e2d304758>


  Mrv1652306172221472D          

 10 10  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
M  CHG  1  10  -1
M  END
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3D MOL for #<Metabolite:0x00007f2e2d304758>

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3D SDF for #<Metabolite:0x00007f2e2d304758>

  Mrv1652306172221472D          

 10 10  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
M  CHG  1  10  -1
M  END
> <DATABASE_ID>
MMDBc0055238

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=CC(=O)C([O-])=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O3/c1-4-2-6(9)7(10)3-5(4)8/h2-3,10H,1H3/p-1

> <INCHI_KEY>
BMBZVGUSOUAIMK-UHFFFAOYSA-M

> <FORMULA>
C7H5O3

> <MOLECULAR_WEIGHT>
137.115

> <EXACT_MASS>
137.024417601

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.366191577611012

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methyl-3,6-dioxocyclohexa-1,4-dien-1-olate

> <JCHEM_LOGP>
0.9010066193333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.119153970368877

> <JCHEM_PKA_STRONGEST_BASIC>
-5.0517420533608695

> <JCHEM_POLAR_SURFACE_AREA>
57.2

> <JCHEM_REFRACTIVITY>
47.9036

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-methyl-3,6-dioxocyclohexa-1,4-dien-1-olate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f2e2d304758>
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PDB for #<Metabolite:0x00007f2e2d304758>
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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O-1
CONECT    1    4                                                            
CONECT    2    4    6                                                       
CONECT    3    5    7                                                       
CONECT    4    1    2    5                                                  
CONECT    5    3    4    8                                                  
CONECT    6    2    7    9                                                  
CONECT    7    3    6   10                                                  
CONECT    8    5                                                            
CONECT    9    6                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for #<Metabolite:0x00007f2e2d304758>
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SMILES for #<Metabolite:0x00007f2e2d304758>
CC1=CC(=O)C([O-])=CC1=O
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INCHI for #<Metabolite:0x00007f2e2d304758>
InChI=1S/C7H6O3/c1-4-2-6(9)7(10)3-5(4)8/h2-3,10H,1H3/p-1
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Synonyms
ValueSource
2-Hydroxy-5-methylquinoneChEBI
2-Hydroxy-5-methylquinone(1-)ChEBI
Molecular FormulaC7H5O3
Average Mass137.115
Monoisotopic Mass137.024417601
IUPAC Name4-methyl-3,6-dioxocyclohexa-1,4-dien-1-olate
Traditional Name4-methyl-3,6-dioxocyclohexa-1,4-dien-1-olate
CAS Registry NumberNot Available
SMILES
CC1=CC(=O)C([O-])=CC1=O
InChI Identifier
InChI=1S/C7H6O3/c1-4-2-6(9)7(10)3-5(4)8/h2-3,10H,1H3/p-1
InChI KeyBMBZVGUSOUAIMK-UHFFFAOYSA-M