General Information of MET (ID: META01214)
Name 2,5-Dihydroxybenzoic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
2,5-DIHYDROXYBENZOIC ACID; gentisic acid; 490-79-9; Benzoic acid, 2,5-dihydroxy-; Hydroquinonecarboxylic acid; Gentisate; 5-Hydroxysalicylic acid; Gensigen; Gensigon; 2,5-Dioxybenzoic acid; 2,5-Dhba; Gentisinic acid; Salicylic acid, 5-hydroxy-; Kyselina gentisinova; Gentisinate; UNII-VP36V95O3T; MFCD00002460; NSC 27224; Kyselina 2,5-dihydroxybenzoova; 3,6-dihydroxybenzoic acid; 2,5-Dihydroxy benzoic acid; CHEMBL1461; VP36V95O3T; CHEBI:17189; BENZOIC ACID,2,5-DIHYDROXY; Gentinatre; Gentalpin; Gentasol
Source Aromatic homomonocyclic compounds
Structure Type   Benzoic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Benzenoids
Benzene and substituted derivatives
Benzoic acids and derivatives
PubChem CID
3469
HMDB ID
HMDB0000152
Formula
C7H6O4
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00628
ChEBI ID
17189
FooDB ID
FDB000844
ChemSpider ID
3350
METLIN ID
618
Physicochemical Properties Molecular Weight 154.12 Topological Polar Surface Area 77.8
XlogP 1.6 Complexity 157
Heavy Atom Count 11 Rotatable Bond Count 1
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Function
Gentisic acid, also known as gentisate or 2,5-dioxybenzoate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. Gentisic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Gentisic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Gentisic acid is found, on average, in the highest concentration within a few different foods, such as tarragons, common thymes, and common sages and in a lower concentration in grape wines, rosemaries, and sweet marjorams. Gentisic acid has also been detected, but not quantified in, several different foods, such as common grapes, fennels, german camomiles, evening primroses, and guava. This could make gentisic acid a potential biomarker for the consumption of these foods. Gentisic acid is also a byproduct of tyrosine and benzoate metabolism. There is an increasing amount of evidence indicating that gentisic acid has a broad spectrum of biological activity, such as anti-inflammatory, antirheumatic and antioxidant properties. Gentisic acid is an active metabolite of salicylic acid degradation. It is a crystalline powder that forms monoclinic prism in water solution. It is a fungal metabolite as well (ChEBI). Gentisic acid is a dihydroxybenzoic acid.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transcription factor (TF)
            R2R3-MYB (AN2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of AN2
                      Induced Change 2,5-Dihydroxybenzoic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the increase of 2,5-dihydroxybenzoic acid levels compared with control group.
References
1 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.

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