Showing metabocard for 2,3-Dihydroxybenzoate (MMDBc0049960)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 22:47:08 UTC
Update Date2022-09-01 02:17:35 UTC
Metabolite IDMMDBc0049960
Metabolite Identification
Common Name2,3-Dihydroxybenzoate
Description2-Pyrocatechuic acid is a normal human benzoic acid metabolite found in plasma (PMID 16351159 ), and is normally found with increased levels after consumption of many nutrients and drugs, i.e.: cranberry juice (PMID 14733499 ), aspirin ingestion. (PMID 3342084 ) It has been found associated with idiopathic oro-facial pain due to stress (oxidative stress might enhance the production of free radicals); it has been suggested that OH radicals are responsible for the production of many systemic and local tissue injury diseases which may initially manifest as pain syndrome, and 2-Pyrocatechuic acid is a biological marker for the detection and quantification of OH radicals, and patients had significantly increased circulating levels of 2-Pyrocatechuic acid after aspirin ingestion than control subjects. (PMID 7748148 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f92580da678>


  Mrv1652309272007362D          

 11 11  0  0  0  0            999 V2000
    0.5024    0.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    1.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9265    0.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9265   -0.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2121   -0.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5024   -0.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2120    2.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6410    1.2155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2168    1.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2168    2.0407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9313    0.8032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f92580da678>

HMDB0000397
     RDKit          3D
2-Pyrocatechuic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.6208    1.1107   -0.6651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -0.0168   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9992   -1.1302   -0.4258 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7526   -0.2307   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2333   -1.4779    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095   -1.6722    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9307   -0.5563    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4498    0.7059    0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3077    1.7655    0.1087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129    0.8679   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659    2.0983   -0.4223 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3407   -1.4267    0.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9205   -2.3374    0.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749   -2.6594    0.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9740   -0.7077    0.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0609    2.7252   -0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0868    2.9421   -0.4406 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  1  0
  8 10  2  0
 10 11  1  0
 10  4  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  9 16  1  0
 11 17  1  0
M  END
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3D SDF for #<Metabolite:0x00007f92580da678>


  Mrv1652309272007362D          

 11 11  0  0  0  0            999 V2000
    0.5024    0.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    1.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9265    0.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9265   -0.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2121   -0.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5024   -0.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2120    2.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6410    1.2155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2168    1.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2168    2.0407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9313    0.8032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049960

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)

> <INCHI_KEY>
GLDQAMYCGOIJDV-UHFFFAOYSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.707382424253517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-dihydroxybenzoic acid

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.6736980806666664

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.64422447107911

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5588607789007356

> <JCHEM_PKA_STRONGEST_BASIC>
-6.335994161973777

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
37.275999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxy-benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f92580da678>

HMDB0000397
     RDKit          3D
2-Pyrocatechuic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.6208    1.1107   -0.6651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -0.0168   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9992   -1.1302   -0.4258 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7526   -0.2307   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2333   -1.4779    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095   -1.6722    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9307   -0.5563    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4498    0.7059    0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3077    1.7655    0.1087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129    0.8679   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659    2.0983   -0.4223 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3407   -1.4267    0.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9205   -2.3374    0.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749   -2.6594    0.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9740   -0.7077    0.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0609    2.7252   -0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0868    2.9421   -0.4406 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  1  0
  8 10  2  0
 10 11  1  0
 10  4  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  9 16  1  0
 11 17  1  0
M  END
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PDB for #<Metabolite:0x00007f92580da678>

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       0.938   1.499   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.396   2.269   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.729   1.499   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.729  -0.041   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.396  -0.811   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.938  -0.041   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.396   3.809   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -3.063   2.269   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.271   2.269   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.271   3.809   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.605   1.499   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2                                                            
CONECT    8    3                                                            
CONECT    9    1   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x00007f92580da678>

COMPND    HMDB0000397
HETATM    1  O1  UNL     1       2.621   1.111  -0.665  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.174  -0.017  -0.433  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.999  -1.130  -0.426  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.753  -0.231  -0.155  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.233  -1.478   0.106  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.109  -1.672   0.368  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.931  -0.556   0.359  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.450   0.706   0.103  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.308   1.765   0.109  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.113   0.868  -0.153  1.00  0.00           C  
HETATM   11  O4  UNL     1       0.466   2.098  -0.422  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.341  -1.427   0.485  1.00  0.00           H  
HETATM   13  H2  UNL     1       0.920  -2.337   0.103  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.475  -2.659   0.566  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.974  -0.708   0.563  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.061   2.725  -0.065  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.087   2.942  -0.441  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5   10
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7    8   15
CONECT    8    9   10   10
CONECT    9   16
CONECT   10   11
CONECT   11   17
END
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SMILES for #<Metabolite:0x00007f92580da678>

OC(=O)C1=C(O)C(O)=CC=C1
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INCHI for #<Metabolite:0x00007f92580da678>

InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)
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Synonyms
ValueSource
2,3 DHBChEBI
2,3-DIHYDROXY-benzoIC ACIDChEBI
3-Hydroxysalicylic acidChEBI
Catechol-3-carboxylic acidChEBI
DOBKChEBI
O-Pyrocatechuic acidChEBI
Pyrocatechuic acidChEBI
2,3-Dihydroxybenzoic acidKegg
2,3-DIHYDROXY-benzoateGenerator
3-HydroxysalicylateGenerator
Catechol-3-carboxylateGenerator
O-PyrocatechuateGenerator
PyrocatechuateGenerator
2,3-DihydroxybenzoateGenerator
2-PyrocatechuateGenerator
CatecholcarboxylateHMDB
Catecholcarboxylic acidHMDB
DHBAHMDB
2,3-Dihydroxy benzoic acidMeSH, HMDB
2-Pyrocatechuic acid, sodium saltMeSH, HMDB
Ferri-2,3-dihydroxybenzoic acidMeSH, HMDB
1,2-Dihydroxybenzene-3-carboxylic acidPhytoBank
Molecular FormulaC7H6O4
Average Mass154.121
Monoisotopic Mass154.026608673
IUPAC Name2,3-dihydroxybenzoic acid
Traditional Name2,3-dihydroxy-benzoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=C(O)C(O)=CC=C1
InChI Identifier
InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)
InChI KeyGLDQAMYCGOIJDV-UHFFFAOYSA-N