CHEBI:17189 - 2,5-dihydroxybenzoic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 2,5-dihydroxybenzoic acid
ChEBI ID CHEBI:17189
Definition A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:19381, CHEBI:19382, CHEBI:11451, CHEBI:936
Supplier Information eMolecules:1934497, ZINC000004655377
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Atrazine ( A-trə-zeen) is a chlorinated herbicide of the triazine class. It is used to prevent pre-emergence broadleaf weeds in crops such as maize (corn), soybean and sugarcane and on turf, such as golf courses and residential lawns. Atrazine's primary manufacturer is Syngenta and it is one of the most widely used herbicides in the United States, Canadian, and Australian agriculture. Its use was banned in the European Union in 2004, when the EU found groundwater levels exceeding the limits set by regulators, and Syngenta could not show that this could be prevented nor that these levels were safe. At least two significant Canadian farm well studies showed that atrazine was the most common contaminant found. As of 2001, atrazine was the most commonly detected pesticide contaminating drinking water in the U.S.: 44  Studies suggest it is an endocrine disruptor, an agent that can alter the natural hormonal system. However, in 2006 the U.S. Environmental Protection Agency (EPA) had stated that under the Food Quality Protection Act "the risks associated with the pesticide residues pose a reasonable certainty of no harm", and in 2007, the EPA said that atrazine does not adversely affect amphibian sexual development and that no additional testing was warranted. The EPA's 2009 review concluded that "the agency's scientific bases for its regulation of atrazine are robust and ensure prevention of exposure levels that could lead to reproductive effects in humans". However, in their 2016 Refined Ecological Risk Assessment for Atrazine, it was stated that "it is difficult to make definitive conclusions about the impact of atrazine at a given concentration but multiple studies have reported effects to various endpoints at environmentally-relevant concentrations." EPA started a registration review in 2013. The EPA's review has been criticized, and the safety of atrazine remains controversial. EPA has however stated that "If at any time EPA determines there are urgent human or environmental risks from atrazine exposure that require prompt attention, we will take appropriate regulatory action, regardless of the status of the registration review process."
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Formula C7H6O4
Net Charge 0
Average Mass 154.12014
Monoisotopic Mass 154.02661
InChI InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
InChIKey WXTMDXOMEHJXQO-UHFFFAOYSA-N
SMILES OC(=O)c1cc(O)ccc1O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Tremella fuciformis (NCBI:txid64657) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor
A lipoxygenase inhibitor that interferes with the action of arachidonate 15-lipoxygenase (EC 1.13.11.33).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Application(s): MALDI matrix material
A compound used to form the matrix for MALDI (matrix-assisted laser desorption/ionization) mass spectrometry. MALDI matrix materials are crystalline compounds with a fairly low molecular weight, so as to allow facile vaporization, have strong absorption at UV or IR wavelengths (to rapidly and efficiently absorb laser irradiation), generally contain polar groups (enabling them to be used in aqueous solutions) and are frequently acidic (so assisting ionisation of the compound being studied, which is contained within the matrix material).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 2,5-dihydroxybenzoic acid (CHEBI:17189) has functional parent benzoic acid (CHEBI:30746)
2,5-dihydroxybenzoic acid (CHEBI:17189) has role EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor (CHEBI:64996)
2,5-dihydroxybenzoic acid (CHEBI:17189) has role fungal metabolite (CHEBI:76946)
2,5-dihydroxybenzoic acid (CHEBI:17189) has role human metabolite (CHEBI:77746)
2,5-dihydroxybenzoic acid (CHEBI:17189) has role MALDI matrix material (CHEBI:64345)
2,5-dihydroxybenzoic acid (CHEBI:17189) has role mouse metabolite (CHEBI:75771)
2,5-dihydroxybenzoic acid (CHEBI:17189) is a dihydroxybenzoic acid (CHEBI:23778)
2,5-dihydroxybenzoic acid (CHEBI:17189) is conjugate acid of 2,5-dihydroxybenzoate (CHEBI:58044)
Incoming 2,5-dihydroxybenzoic acid 2-O-β-D-glucoside (CHEBI:136922) has functional parent 2,5-dihydroxybenzoic acid (CHEBI:17189)
2,5-dihydroxybenzoic acid 5-O-β-D-glucoside (CHEBI:136772) has functional parent 2,5-dihydroxybenzoic acid (CHEBI:17189)
2,5-dihydroxybenzoyl-CoA (CHEBI:90176) has functional parent 2,5-dihydroxybenzoic acid (CHEBI:17189)
benzyl 2,5-dihydroxybenzoate (CHEBI:155896) has functional parent 2,5-dihydroxybenzoic acid (CHEBI:17189)
mygalin (CHEBI:64901) has functional parent 2,5-dihydroxybenzoic acid (CHEBI:17189)
2,5-dihydroxybenzoate (CHEBI:58044) is conjugate base of 2,5-dihydroxybenzoic acid (CHEBI:17189)
IUPAC Name
2,5-dihydroxybenzoic acid
Synonyms Sources
2,5-Dihydroxybenzoate KEGG COMPOUND
2,5-dihydroxybenzoic acid ChEBI
2,5-Dihydroxybenzoic acid KEGG COMPOUND
5-hydroxysalicylic acid ChEBI
Gentisate KEGG COMPOUND
Gentisic acid KEGG COMPOUND
Hydroquinonecarboxylic acid KEGG COMPOUND
Manual Xrefs Databases
3260 DrugCentral
C00002648 KNApSAcK
C00628 KEGG COMPOUND
CPD-633 MetaCyc
Gentisic_acid Wikipedia
GTQ PDBeChem
HMDB0000152 HMDB
LSM-19031 LINCS
View more database links
Registry Numbers Types Sources
2209119 Reaxys Registry Number Reaxys
490-79-9 CAS Registry Number KEGG COMPOUND
490-79-9 CAS Registry Number ChemIDplus
Citations Types Sources
15862799 PubMed citation Europe PMC
18314336 PubMed citation Europe PMC
22770225 PubMed citation Europe PMC
24547933 PubMed citation Europe PMC
Last Modified
19 June 2020