Showing metabocard for Pyrocatechol (MMDBc0048005)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-19 21:49:31 UTC
Update Date2024-10-07 02:13:53 UTC
Metabolite IDMMDBc0048005
Metabolite Identification
Common NamePyrocatechol
DescriptionPyrocatechol, often known as catechol or benzene-1,2-diol, is a benzenediol, with formula C6H4(OH)2. It was first prepared in 1839 by H. Reinsch by distilling catechin (the juice of Mimosa catechu). This colourless compound occurs naturally, but about 20000 tons are manufactured each year, mainly as precursors to pesticides, flavors, and fragrances. Its sulfonic acid is often present in the urine of many mammals. Small amounts of catechol occur naturally in fruits and vegetables, along with the enzyme polyphenol oxidase. Upon mixing the enzyme with the substrate and exposure to oxygen (as when a potato or apple is cut), the colorless catechol oxidizes to reddish-brown benzoquinone derivatives. The enzyme is inactivated by adding an acid, such as lemon juice, or by refrigeration. Excluding oxygen also prevents the browning reaction. Catechol melts at 28 °C and boils at 250 °C. It is employed in medicine as an expectorant. The dimethyl ether or veratrol is also used in medicine. Many other pyrocatechin derivatives have been suggested for therapeutic application. Pyrocatechol has also been found to be a microbial metabolite in Escherichia, Mycobacterium and Pseudomonas (PMID:19300498 ; PMID:25281236 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000559d01022ff8>


  Mrv1652309272007412D          

  8  8  0  0  0  0            999 V2000
    0.0000    0.8250    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    0.4125    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
    0.0000   -0.8250    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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  6  2  2  0  0  0  0
  1  8  1  0  0  0  0
  3  7  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000559d01022ff8>

HMDB0000957
     RDKit          3D
Pyrocatechol
 14 14  0  0  0  0  0  0  0  0999 V2000
    1.6743   -1.6790    0.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996   -0.8057    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -1.2721    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7721   -0.4071   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088    0.9633   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196    1.4455   -0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698    0.5578   -0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0526    1.0989   -0.0109 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6461   -1.4306    0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8196   -2.3565    0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7883   -0.8049    0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4704    1.6115   -0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1324    2.5191   -0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8826    0.5599    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
M  END
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3D SDF for #<Metabolite:0x0000559d01022ff8>


  Mrv1652309272007412D          

  8  8  0  0  0  0            999 V2000
    0.0000    0.8250    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    0.4125    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
    0.0000   -0.8250    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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  6  2  2  0  0  0  0
  1  8  1  0  0  0  0
  3  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0048005

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=C(O)C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H

> <INCHI_KEY>
YCIMNLLNPGFGHC-UHFFFAOYSA-N

> <FORMULA>
C6H6O2

> <MOLECULAR_WEIGHT>
110.1106

> <EXACT_MASS>
110.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.692303526357614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzene-1,2-diol

> <ALOGPS_LOGP>
0.74

> <JCHEM_LOGP>
1.3661151726666665

> <ALOGPS_LOGS>
-0.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.794732100904419

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.342309260967141

> <JCHEM_PKA_STRONGEST_BASIC>
-6.287220763519362

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
30.019799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.50e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
catechol

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x0000559d01022ff8>

HMDB0000957
     RDKit          3D
Pyrocatechol
 14 14  0  0  0  0  0  0  0  0999 V2000
    1.6743   -1.6790    0.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996   -0.8057    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -1.2721    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7721   -0.4071   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088    0.9633   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196    1.4455   -0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698    0.5578   -0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0526    1.0989   -0.0109 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6461   -1.4306    0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8196   -2.3565    0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7883   -0.8049    0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4704    1.6115   -0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1324    2.5191   -0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8826    0.5599    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
M  END
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PDB for #<Metabolite:0x0000559d01022ff8>

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
CONECT    1    2    3    8                                                  
CONECT    2    1    6                                                       
CONECT    3    1    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2                                                       
CONECT    7    3                                                            
CONECT    8    1                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for #<Metabolite:0x0000559d01022ff8>

COMPND    HMDB0000957
HETATM    1  O1  UNL     1       1.674  -1.679   0.041  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.600  -0.806   0.019  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.714  -1.272   0.021  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.772  -0.407  -0.001  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.609   0.963  -0.027  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.320   1.445  -0.029  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.770   0.558  -0.007  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.053   1.099  -0.011  1.00  0.00           O  
HETATM    9  H1  UNL     1       2.646  -1.431   0.041  1.00  0.00           H  
HETATM   10  H2  UNL     1      -0.820  -2.357   0.041  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.788  -0.805   0.002  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.470   1.612  -0.043  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.132   2.519  -0.049  1.00  0.00           H  
HETATM   14  H6  UNL     1       2.883   0.560   0.004  1.00  0.00           H  
CONECT    1    2    9
CONECT    2    3    3    7
CONECT    3    4   10
CONECT    4    5    5   11
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7    8
CONECT    8   14
END
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SMILES for #<Metabolite:0x0000559d01022ff8>

OC1=C(O)C=CC=C1
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INCHI for #<Metabolite:0x0000559d01022ff8>

InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
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Synonyms
ValueSource
1,2-BenzenediolChEBI
1,2-DihydroxybenzeneChEBI
2-HydroxyphenolChEBI
alpha-HydroxyphenolChEBI
BrenzcatechinChEBI
O-BenzenediolChEBI
O-HydroxyphenolChEBI
PyrocatechinChEBI
a-HydroxyphenolGenerator
Α-hydroxyphenolGenerator
CatecholHMDB
Durafur developer CHMDB
Fouramine PCHHMDB
Fourrine 68HMDB
O-DihydroxybenzeneHMDB
O-DioxybenzeneHMDB
O-HydroquinoneHMDB
O-PhenylenediolHMDB
OxyphenateHMDB
Oxyphenic acidHMDB
Pelagol grey CHMDB
PhthalhydroquinoneHMDB
Phthalic alcoholHMDB
PyrocatechineHMDB
1,3-DihydroxybenzeneHMDB
Catechol dipotassium saltHMDB
Catechol, 14C-labeled CPDHMDB
Catechol sodium saltHMDB
Benzene-1,2-diolPhytoBank
PyrocatecholPhytoBank
1,2-HydroxybenzenePhytoBank
Molecular FormulaC6H6O2
Average Mass110.1106
Monoisotopic Mass110.036779436
IUPAC Namebenzene-1,2-diol
Traditional Namecatechol
CAS Registry NumberNot Available
SMILES
OC1=C(O)C=CC=C1
InChI Identifier
InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
InChI KeyYCIMNLLNPGFGHC-UHFFFAOYSA-N