Showing metabocard for 2,5-dihydroxybenzoic acid (MMDBc0054204)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 22:58:37 UTC
Update Date2025-10-07 16:08:25 UTC
Metabolite IDMMDBc0054204
Metabolite Identification
Common Name2,5-dihydroxybenzoic acid
Description2,5-dihydroxybenzoic acid is a phenolic compound belonging to the class of organic acids. Its chemical structure features a benzene ring with two hydroxyl groups at the 2 and 5 positions, contributing to its reactivity and biological functions. This metabolite is involved in various biochemical pathways, including iron transport, where it acts as a siderophore to facilitate iron entry into mitochondria, as observed in MEL cells (PMID:40957995 ). Additionally, it has been implicated in metabolic processes, such as ameliorating metabolic dysfunction-associated steatotic liver disease by targeting the CCL2-CCR2 axis to reduce lipid accumulation (PMID:40507104 ). The green Mediterranean diet has also been shown to elevate plasma levels of 2,5-dihydroxybenzoic acid, suggesting its role in hepatic lipid metabolism (PMID:40507104 ). Furthermore, it is associated with starch and sucrose metabolism and tyrosine metabolism pathways, indicating its potential significance in plant responses to environmental stressors, such as flooding and hypoxia (PMID:40350109 ). Its utility extends to analytical applications, where it serves as a matrix in mass spectrometry for tissue analysis (PMID:40693997 ).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f2e38e2d8e0>


  Mrv1533004231515392D          

 11 11  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
    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
    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    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
  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
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  CHG  1  11  -1
M  END
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3D MOL for #<Metabolite:0x00007f2e38e2d8e0>

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3D SDF for #<Metabolite:0x00007f2e38e2d8e0>

  Mrv1533004231515392D          

 11 11  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
    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
    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    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
  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
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  CHG  1  11  -1
M  END
> <DATABASE_ID>
MMDBc0054204

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=CC=C(O)C(=C1)C([O-])=O

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

> <INCHI_KEY>
WXTMDXOMEHJXQO-UHFFFAOYSA-M

> <FORMULA>
C7H5O4

> <MOLECULAR_WEIGHT>
153.114

> <EXACT_MASS>
153.019332221

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
13.332106388455845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dihydroxybenzoate

> <ALOGPS_LOGP>
0.65

> <JCHEM_LOGP>
1.6736980806666664

> <ALOGPS_LOGS>
-0.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.024335409652737

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5281776702814094

> <JCHEM_PKA_STRONGEST_BASIC>
-5.934430569892133

> <JCHEM_POLAR_SURFACE_AREA>
80.59

> <JCHEM_REFRACTIVITY>
48.1131

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gentisate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f2e38e2d8e0>
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PDB for #<Metabolite:0x00007f2e38e2d8e0>
HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-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  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+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  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   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:0x00007f2e38e2d8e0>
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SMILES for #<Metabolite:0x00007f2e38e2d8e0>
OC1=CC=C(O)C(=C1)C([O-])=O
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INCHI for #<Metabolite:0x00007f2e38e2d8e0>
InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)/p-1
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Synonyms
ValueSource
2,5-Dihydroxybenzoate anionChEBI
5-HydroxysalicylateChEBI
GentisateChEBI
HydroquinonecarboxylateChEBI
2,5-Dihydroxybenzoic acid anionGenerator
5-Hydroxysalicylic acidGenerator
Gentisic acidGenerator
Hydroquinonecarboxylic acidGenerator
2,5-Dihydroxybenzoic acidGenerator
Molecular FormulaC7H5O4
Average Mass153.114
Monoisotopic Mass153.019332221
IUPAC Name2,5-dihydroxybenzoate
Traditional Namegentisate
CAS Registry NumberNot Available
SMILES
OC1=CC=C(O)C(=C1)C([O-])=O
InChI Identifier
InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)/p-1
InChI KeyWXTMDXOMEHJXQO-UHFFFAOYSA-M