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Showing metabocard for 2-Pyrocatechuic acid (HMDB0000397)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
enzymes (4) Show 4 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:47 UTC
HMDB IDHMDB0000397
Secondary Accession Numbers
  • HMDB00397
Metabolite Identification
Common Name2-Pyrocatechuic acid
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
Data?1676999687
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000397 (2-Pyrocatechuic acid)


  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
Download

3D MOL for HMDB0000397 (2-Pyrocatechuic acid)

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
Download

3D SDF for HMDB0000397 (2-Pyrocatechuic acid)


  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>
HMDB0000397

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0000397 (2-Pyrocatechuic acid)

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 HMDB0000397 (2-Pyrocatechuic acid)

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 HMDB0000397 (2-Pyrocatechuic acid)

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 HMDB0000397 (2-Pyrocatechuic acid)

OC(=O)C1=C(O)C(O)=CC=C1
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INCHI for HMDB0000397 (2-Pyrocatechuic acid)

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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View in JSmolView NMR AssignmentsView Stereo Labels
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
Chemical FormulaC7H6O4
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
IUPAC Name2,3-dihydroxybenzoic acid
Traditional Name2,3-dihydroxy-benzoic acid
CAS Registry Number303-38-8
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylic acids
Alternative Parents
Substituents
  • Salicylic acid
  • Benzoic acid
  • Benzoyl
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point204.00 to 208.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point362.00 to 363.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility26120 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.20HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available120.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000290
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.88 g/LALOGPS
logP1.42ALOGPS
logP1.67ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.56ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m³·mol⁻¹ChemAxon
Polarizability13.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.8431661259
DarkChem[M-H]-126.56931661259
AllCCS[M+H]+132.72132859911
AllCCS[M-H]-125.72232859911
DeepCCS[M+H]+130.68530932474
DeepCCS[M-H]-127.90730932474
DeepCCS[M-2H]-164.3230932474
DeepCCS[M+Na]+139.71730932474
AllCCS[M+H]+132.732859911
AllCCS[M+H-H2O]+128.232859911
AllCCS[M+NH4]+137.032859911
AllCCS[M+Na]+138.232859911
AllCCS[M-H]-125.732859911
AllCCS[M+Na-2H]-127.032859911
AllCCS[M+HCOO]-128.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Pyrocatechuic acidOC(=O)C1=C(O)C(O)=CC=C12636.8Standard polar33892256
2-Pyrocatechuic acidOC(=O)C1=C(O)C(O)=CC=C11473.1Standard non polar33892256
2-Pyrocatechuic acidOC(=O)C1=C(O)C(O)=CC=C11378.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Pyrocatechuic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC(O)=C1O1646.4Semi standard non polar33892256
2-Pyrocatechuic acid,1TMS,isomer #2C[Si](C)(C)OC1=C(O)C=CC=C1C(=O)O1664.0Semi standard non polar33892256
2-Pyrocatechuic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=CC(C(=O)O)=C1O1650.0Semi standard non polar33892256
2-Pyrocatechuic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C)=C1O1667.4Semi standard non polar33892256
2-Pyrocatechuic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC=CC(O)=C1O[Si](C)(C)C1676.1Semi standard non polar33892256
2-Pyrocatechuic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC=CC(C(=O)O)=C1O[Si](C)(C)C1713.5Semi standard non polar33892256
2-Pyrocatechuic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C1743.7Semi standard non polar33892256
2-Pyrocatechuic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O)=C1O1919.1Semi standard non polar33892256
2-Pyrocatechuic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O)C=CC=C1C(=O)O1943.1Semi standard non polar33892256
2-Pyrocatechuic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC(C(=O)O)=C1O1929.2Semi standard non polar33892256
2-Pyrocatechuic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O2155.6Semi standard non polar33892256
2-Pyrocatechuic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O)=C1O[Si](C)(C)C(C)(C)C2142.8Semi standard non polar33892256
2-Pyrocatechuic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC(C(=O)O)=C1O[Si](C)(C)C(C)(C)C2216.0Semi standard non polar33892256
2-Pyrocatechuic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2408.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Pyrocatechuic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0924000000-1ed6156dbe82344d29af2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (3 TMS)splash10-0a4u-3922000000-0b326da278c57df03c1a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Pyrocatechuic acid GC-EI-TOF (Non-derivatized)splash10-0a4i-0924000000-1ed6156dbe82344d29af2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (Non-derivatized)splash10-0a4u-3922000000-0b326da278c57df03c1a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Pyrocatechuic acid GC-EI-TOF (Non-derivatized)splash10-0a4l-0922000000-beddd6836f31d4813a142017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zg0-4900000000-44419ba3a3e768caaeee2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (3 TMS) - 70eV, Positivesplash10-008a-5192000000-86efa4079dcb0a7d61742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pyrocatechuic acid GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Pyrocatechuic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-0zfr-0900000000-9d9306f70123d5d263ef2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Pyrocatechuic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0a4i-4900000000-702a14e999a2e830a9d52012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Pyrocatechuic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0a4i-7900000000-a88a9646fb3070aef98d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Pyrocatechuic acid Linear Ion Trap , negative-QTOFsplash10-0a4i-0900000000-9bbc26971da28557772e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Pyrocatechuic acid , negative-QTOFsplash10-0pb9-0900000000-7f5ec409ec11ea326d422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Pyrocatechuic acid Linear Ion Trap , positive-QTOFsplash10-0a4i-0900000000-ba9640b66d655cdb32952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Pyrocatechuic acid Linear Ion Trap , positive-QTOFsplash10-0201-0900000000-40f4ec4c2b33e147f78b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Pyrocatechuic acid 40V, Negative-QTOFsplash10-0a4i-6900000000-c5444a948b6dfffe40592021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Pyrocatechuic acid 35V, Negative-QTOFsplash10-0a4i-0900000000-6000163ae935d019ab252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Pyrocatechuic acid 35V, Negative-QTOFsplash10-0pb9-0900000000-b9e3e795548fcdc52ee42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Pyrocatechuic acid 20V, Negative-QTOFsplash10-0a4i-2900000000-9aef155a0507c9c6d9862021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Pyrocatechuic acid 10V, Negative-QTOFsplash10-0pb9-0900000000-5d283030559c5931b8242021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pyrocatechuic acid 10V, Positive-QTOFsplash10-0a4i-0900000000-68a4f0df325353ecd0822017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pyrocatechuic acid 20V, Positive-QTOFsplash10-0a4r-0900000000-1b11ae0f71a80e056a932017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pyrocatechuic acid 40V, Positive-QTOFsplash10-0udi-9200000000-f64ac01c6efb684a4f552017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pyrocatechuic acid 10V, Negative-QTOFsplash10-0zfr-0900000000-cb45151fcc0e74008de32017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pyrocatechuic acid 20V, Negative-QTOFsplash10-0a4i-0900000000-df3ca8c192f0fcf2b6202017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pyrocatechuic acid 40V, Negative-QTOFsplash10-0a4i-9700000000-e3faafae5f2aad580cdd2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pyrocatechuic acid 10V, Positive-QTOFsplash10-000i-0900000000-f9afef76ab6c6ac97e512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pyrocatechuic acid 20V, Positive-QTOFsplash10-0a4i-5900000000-0ca2af142a25251b2a852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pyrocatechuic acid 40V, Positive-QTOFsplash10-0ue9-9100000000-18f4a8eefdb99c1dd8ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pyrocatechuic acid 10V, Negative-QTOFsplash10-0a4i-0900000000-31cc76875b7e828b57e32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pyrocatechuic acid 20V, Negative-QTOFsplash10-0a4i-2900000000-2b91af5de3160a31b13d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pyrocatechuic acid 40V, Negative-QTOFsplash10-066u-9100000000-1810b7542f18d07d2e102021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 430 details
BloodDetected and Quantified0.129 +/- 0.034 uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.11 +/- 0.08 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.11 +/- 0.031 uMAdult (>18 years old)BothIdiopathic oro-facial pain details
UrineDetected and Quantified0.14 +/- 0.05 umol/mmol creatinineAdult (>18 years old)BothIdiopathic oro-facial pain details
Associated Disorders and Diseases
Disease References
Idiopathic oro-facial pain
  1. Aghabeigi B, Haque M, Wasil M, Hodges SJ, Henderson B, Harris M: The role of oxygen free radicals in idiopathic facial pain. Br J Oral Maxillofac Surg. 1997 Jun;35(3):161-5. [PubMed:9212290 ]
Associated OMIM IDsNone
DrugBank IDDB01672
Phenol Explorer Compound ID430
FooDB IDFDB012200
KNApSAcK IDC00002669
Chemspider ID18
KEGG Compound IDC00196
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,3-Dihydroxybenzoic_acid
METLIN ID5386
PubChem Compound19
PDB IDNot Available
ChEBI ID18026
Food Biomarker OntologyNot Available
VMH ID23DHB
MarkerDB IDNot Available
Good Scents IDrw1161691
References
Synthesis ReferenceMega, Izumi; Ozawa, Shuji. Manufacture of 2,3-dihydroxybenzoic acid. Jpn. Kokai Tokkyo Koho (2001), 3 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. A J, Trygg J, Gullberg J, Johansson AI, Jonsson P, Antti H, Marklund SL, Moritz T: Extraction and GC/MS analysis of the human blood plasma metabolome. Anal Chem. 2005 Dec 15;77(24):8086-94. [PubMed:16351159 ]
  2. Grootveld M, Halliwell B: Aromatic hydroxylation as a potential measure of hydroxyl-radical formation in vivo. Identification of hydroxylated derivatives of salicylate in human body fluids. Biochem J. 1986 Jul 15;237(2):499-504. [PubMed:3026319 ]
  3. Kaur H, Edmonds SE, Blake DR, Halliwell B: Hydroxyl radical generation by rheumatoid blood and knee joint synovial fluid. Ann Rheum Dis. 1996 Dec;55(12):915-20. [PubMed:9014586 ]
  4. Schulz JB, Dehmer T, Schols L, Mende H, Hardt C, Vorgerd M, Burk K, Matson W, Dichgans J, Beal MF, Bogdanov MB: Oxidative stress in patients with Friedreich ataxia. Neurology. 2000 Dec 12;55(11):1719-21. [PubMed:11113228 ]
  5. Grootveld M, Halliwell B: 2,3-Dihydroxybenzoic acid is a product of human aspirin metabolism. Biochem Pharmacol. 1988 Jan 15;37(2):271-80. [PubMed:3342084 ]
  6. Zhang K, Zuo Y: GC-MS determination of flavonoids and phenolic and benzoic acids in human plasma after consumption of cranberry juice. J Agric Food Chem. 2004 Jan 28;52(2):222-7. [PubMed:14733499 ]
  7. Haque MF, Aghabeighi B, Wasil M, Hodges S, Harris M: Oxygen free radicals in idiopathic facial pain. Bangladesh Med Res Counc Bull. 1994 Dec;20(3):104-16. [PubMed:7748148 ]

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
2-Pyrocatechuic acid → 3-Methoxysalicylic aciddetails
2-Pyrocatechuic acid → 3-hydroxy-2-methoxybenzoic aciddetails
Enzyme Details
2. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2-Pyrocatechuic acid → 6-(3-carboxy-2-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-Pyrocatechuic acid → 6-(2-carboxy-6-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-Pyrocatechuic acid → 6-(2,3-dihydroxybenzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Enzyme Details
3. Glycine N-acyltransferase
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
2-Pyrocatechuic acid → 2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}acetic aciddetails
Enzyme Details
4. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
2-Pyrocatechuic acid → 2-hydroxy-3-(sulfooxy)benzoic aciddetails