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MetaCyc Compound: gallate

Synonyms: gallic acid, 3,4,5-trihydroxybenzoic acid, 3,4,5-trihydroxybenzoate, pyrogallol-5-carboxylic acid, pyrogallol-5-carboxylate

Chemical Formula: C7H5O5

Molecular Weight: 169.11 Daltons

Monoisotopic Molecular Weight: 170.0215233031 Daltons

gallate compound structure

SMILES: C([O-])(=O)C1(C=C(C(=C(C=1)O)O)O)

InChI: InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)/p-1


Unification Links: CAS:149-91-7, ChEBI:16918, ChemSpider:3790309, HMDB:HMDB05807, KEGG:c01424, PubChem:54675821, UMBBD-Compounds:c0006

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -120.44646Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

gallate degradation I :
gallate + oxygen → (1E)-4-oxobut-1-ene-1,2,4-tricarboxylate + 2 H+

gallate degradation II :
gallate + oxygen → 2-pyrone-4,6-dicarboxylate + H2O + H+

galloylated catechin biosynthesis , pentagalloylglucose biosynthesis :
UDP-α-D-glucose + gallate → 1-O-galloyl-β-D-glucose + UDP

Reactions known to produce the compound:

gallate biosynthesis :
3,5-didehydroshikimate → gallate

syringate degradation :
3-O-methylgallate + a tetrahydrofolate → gallate + an N5-methyl-tetrahydrofolate

Not in pathways:
digallate + H2O → 2 gallate + H+

Reactions known to both consume and produce the compound:

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

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

Inhibitor (Competitive) of: glutamate decarboxylase A [Youngs91, Helmward89], glutamate decarboxylase B [Youngs91, Helmward89]

This compound has been characterized as an alternative substrate of the following enzymes: protocatechuate 4,5-dioxygenase


Helmward89: Helmward Z "Handbook of Enzyme Inhibitors. 2nd, revised and enlarged edition." Weinheim, Federal Republic of Germany ; New York, NY, USA , 1989.

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

Youngs91: Youngs TL, Tunnicliff G (1991). "Substrate analogues and divalent cations as inhibitors of glutamate decarboxylase from Escherichia coli." Biochem Int 1991;23(5);915-22. PMID: 1883399

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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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