Showing metabocard for 2-hydroxy-1,4-benzoquinone (MMDBc0054168)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 22:56:56 UTC
Update Date2022-09-01 02:27:40 UTC
Metabolite IDMMDBc0054168
Metabolite Identification
Common Name2-hydroxy-1,4-benzoquinone
Description2-hydroxy-1,4-benzoquinone belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. It is formed by the reaction of 1,4-benzoquinone with hydrogen peroxide and is a byproduct of the metabolism of phenols, such as 1,2,4-benzenetriol. 2-hydroxy-1,4-benzoquinone is an extremely weak basic (essentially neutral) compound (based on its pKa). The IUPAC name is 2-hydroxycyclohexa-2,5-diene-1,4-dione. It tends to dimerize spontaneously by peroxo bridges. The enzyme 2-hydroxy-1,4-benzoquinone-2-reductase converts it to 1,4-benzoquinone. The compound is often called 2-hydroxy-1,4-benzoquinone, but the "2-" prefix is superfluous since there is no other hydroxy derivative of 1,4-benzoquinone. The enzyme 1,2,4-benzenetriol dehydrogenase catalyzes the conversion of 1,2,4-benzenetriol to 2-hydroxy-1,4-benzoquinone, and the enzyme hydroxybenzoquinone reductase catalyzes the reverse reaction. It is one of three hydroxybenzoquinone isomers and one of the simplest hydroxyquinones. Hydroxy-1,4-benzoquinone, also called hydroxy-para-benzoquinone, is an organic compound with formula C6H4O3, formally derived from 1,4-Benzoquinone by replacing one hydrogen atom with a hydroxyl (OH) group.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fecf4607d98>


  Mrv1533004161519562D          

  9  9  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 O   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
    1.4289    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
    2.1434   -0.4125    0.0000 O   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
    0.0000    0.0000    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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fecf4607d98>

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3D SDF for #<Metabolite:0x00007fecf4607d98>

  Mrv1533004161519562D          

  9  9  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 O   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
    1.4289    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
    2.1434   -0.4125    0.0000 O   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
    0.0000    0.0000    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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054168

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=CC(=O)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H4O3/c7-4-1-2-5(8)6(9)3-4/h1-3,9H

> <INCHI_KEY>
GPLIMIJPIZGPIF-UHFFFAOYSA-N

> <FORMULA>
C6H4O3

> <MOLECULAR_WEIGHT>
124.095

> <EXACT_MASS>
124.016043989

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
10.656930085035139

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxycyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
-0.07

> <JCHEM_LOGP>
0.50545613

> <ALOGPS_LOGS>
-0.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.032783890481755

> <JCHEM_PKA_STRONGEST_BASIC>
-5.089520326303512

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
32.996199999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-1,4-benzoquinone

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fecf4607d98>
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PDB for #<Metabolite:0x00007fecf4607d98>
HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for #<Metabolite:0x00007fecf4607d98>
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SMILES for #<Metabolite:0x00007fecf4607d98>
OC1=CC(=O)C=CC1=O
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INCHI for #<Metabolite:0x00007fecf4607d98>
InChI=1S/C6H4O3/c7-4-1-2-5(8)6(9)3-4/h1-3,9H
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Synonyms
ValueSource
2-Hydroxy-p-benzoquinoneChEBI
2-Hydroxycyclohexa-2,5-diene-1,4-dioneChEBI
HydroxybenzoquinoneChEBI
Molecular FormulaC6H4O3
Average Mass124.095
Monoisotopic Mass124.016043989
IUPAC Name2-hydroxycyclohexa-2,5-diene-1,4-dione
Traditional Name2-hydroxy-1,4-benzoquinone
CAS Registry NumberNot Available
SMILES
OC1=CC(=O)C=CC1=O
InChI Identifier
InChI=1S/C6H4O3/c7-4-1-2-5(8)6(9)3-4/h1-3,9H
InChI KeyGPLIMIJPIZGPIF-UHFFFAOYSA-N