MetaCyc Compound: pyrogallol

Synonyms: 1,2,3-trihydroxybenzene, 1,2,3-benzenetriol, C.I. Oxidation Base 32, C.I. 76515, fouramine base ap, Fouramine Brown AP, fourrine 85, fourrine PG, Piral, Pyro, pyrogallic acid

Chemical Formula: C6H6O3

Molecular Weight: 126.11 Daltons

Monoisotopic Molecular Weight: 126.0316940589 Daltons

pyrogallol compound structure

SMILES: C1(C=C(O)C(O)=C(C=1)O)

InChI: InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H


Unification Links: ChEBI:16164, ChemSpider:13835557, HMDB:HMDB13674, KEGG:C01108, MetaboLights:MTBLC16164, PubChem:1057, UMBBD-Compounds:c0025

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -27.233282Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

2,2'-dihydroxybiphenyl degradation :
pyrogallol + oxygen → (2Z,4E)-2-hydroxyhexa-2,4-dienedioate + 2 H+

gallate degradation III (anaerobic) :
1,2,3,5-tetrahydroxybenzene + pyrogallol → 1,2,3,5-tetrahydroxybenzene + phloroglucinol

Reactions known to produce the compound:

2,2'-dihydroxybiphenyl degradation :
2,3-dihydroxybenzoate + NADH + oxygen + 2 H+pyrogallol + CO2 + NAD+ + H2O

Reactions known to both consume and produce the compound:

gallate degradation III (anaerobic) :
gallate + H+ ↔ CO2 + pyrogallol

Enzymes inhibited by pyrogallol, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: ethylnitronate monooxygenase [Kido78]

This compound has been characterized as an alternative substrate of the following enzymes: gallate dioxygenase


Kido78: Kido T, Soda K (1978). "Properties of 2-nitropropane dioxygenase of Hansenula mrakii. Formation and participation of superoxide." J Biol Chem 253(1);226-32. PMID: 201619

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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