3,4-dihydroxybenzoic acid (CHEBI:36062)

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ChEBI Name	3,4-dihydroxybenzoic acid

ChEBI ID	CHEBI:36062

Definition	A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:1380, CHEBI:41912, CHEBI:16798, CHEBI:19879, CHEBI:20270, CHEBI:20272

Supplier Information	ChemicalBook:CB3305861, eMolecules:502573, ZINC000000013246

Download	Molfile XML SDF

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Wikipedia	License
Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies. It is produced commercially from vanillin.
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Formula

C7H6O4

Net Charge

Average Mass

154.120

Monoisotopic Mass

154.02661

InChI

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

InChIKey

YQUVCSBJEUQKSH-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC(=C(C=C1)O)O)O

Metabolite of Species	Details
Ficus mucuso (NCBI:txid309328)	Found in fruit (BTO:0000486). Methanolic extract of air-dried and powdered figs(fruits) See: PubMed
Origanum vulgare (NCBI:txid39352)	Found in aerial part (BTO:0001658). 95% EtOH extract of dried and powdered aerial parts See: PubMed
Oryza sativa (NCBI:txid4530)	See: PubMed
Cordyceps sinensis (NCBI:txid72228)	Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed
Alpinia (NCBI:txid94326)	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 1.14.11.2 (procollagen-proline dioxygenase) inhibitor An EC 1.14.11.* (oxidoreductase acting on paired donors, 2-oxoglutarate as one donor, incorporating 1 atom each of oxygen into both donors) inhibitor that interferes with the action of procollagen-proline dioxygenase (EC 1.14.11.2). EC 1.1.1.25 (shikimate dehydrogenase) inhibitor An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of shikimate dehydrogenase (EC 1.1.1.25). human xenobiotic metabolite Any human metabolite produced by metabolism of a xenobiotic compound in humans. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	3,4-dihydroxybenzoic acid (CHEBI:36062) has functional parent benzoic acid (CHEBI:30746) 3,4-dihydroxybenzoic acid (CHEBI:36062) has role antineoplastic agent (CHEBI:35610) 3,4-dihydroxybenzoic acid (CHEBI:36062) has role EC 1.1.1.25 (shikimate dehydrogenase) inhibitor (CHEBI:77484) 3,4-dihydroxybenzoic acid (CHEBI:36062) has role EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor (CHEBI:132365) 3,4-dihydroxybenzoic acid (CHEBI:36062) has role human xenobiotic metabolite (CHEBI:76967) 3,4-dihydroxybenzoic acid (CHEBI:36062) has role plant metabolite (CHEBI:76924) 3,4-dihydroxybenzoic acid (CHEBI:36062) is a catechols (CHEBI:33566) 3,4-dihydroxybenzoic acid (CHEBI:36062) is a dihydroxybenzoic acid (CHEBI:23778) 3,4-dihydroxybenzoic acid (CHEBI:36062) is conjugate acid of 3,4-dihydroxybenzoate (CHEBI:36241)

Incoming	1-(3,4-dihydroxybenzoyl)-β-D-glucopyranose (CHEBI:136876) has functional parent 3,4-dihydroxybenzoic acid (CHEBI:36062) ethyl 3,4-dihydroxybenzoate (CHEBI:132364) has functional parent 3,4-dihydroxybenzoic acid (CHEBI:36062) methyl 3,4-dihydroxybenzoate (CHEBI:132366) has functional parent 3,4-dihydroxybenzoic acid (CHEBI:36062) 3,4-dihydroxybenzoate (CHEBI:36241) is conjugate base of 3,4-dihydroxybenzoic acid (CHEBI:36062)

IUPAC Name

3,4-dihydroxybenzoic acid

Citations

Last Modified

05 July 2016