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MetaCyc Compound: gentisate

Synonyms: gentisic acid, hydroquinonecarboxylic acid, 2,5-dihydroxybenzoate, 2,5-DHBA, 2,5-dihydroxybenzoic acid, 2,5-dioxybenzoic acid, 3,6-dihydroxybenzoic acid, 5-hydroxysalicylic acid, 5-hydroxysalicylate

Superclasses: an acid all carboxy acids a carboxylate a hydroxy carboxylate
an acid all carboxy acids a carboxylate a monocarboxylate

Citations: [Dean08]

Chemical Formula: C7H5O4

Molecular Weight: 153.11 Daltons

Monoisotopic Molecular Weight: 154.026608681 Daltons

gentisate compound structure

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

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

InChIKey: InChIKey=WXTMDXOMEHJXQO-UHFFFAOYSA-M

Unification Links: CAS:490-79-9 , ChEBI:58044 , ChemSpider:144318 , HMDB:HMDB00152 , KEGG:C00628 , MetaboLights:MTBLC58044 , PubChem:54675839

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -80.96645 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

gentisate degradation I , gentisate degradation II , salicylate degradation IV :
gentisate + oxygen → maleylpyruvate + H+

salicylate glucosides biosynthesis II :
gentisate + UDP-α-D-glucose → 2,5-dihydroxybenzoate 5-O-β-D-glucoside + UDP + H+

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

3-chlorobenzoate degradation III (via gentisate) , m-cresol degradation :
3-hydroxybenzoate + NADH + oxygen + H+gentisate + NAD+ + H2O

3-phenylpropanoate degradation :
3-hydroxybenzoyl-CoA + an unknown reduced electron acceptor + oxygen → gentisate + coenzyme A + an unknown oxidized electron acceptor + H+

patulin biosynthesis :
gentisaldehyde + NADP+ + H2O → gentisate + NADPH + 2 H+

salicylate degradation II , salicylate glucosides biosynthesis II :
salicylate + NADH + oxygen + H+gentisate + NAD+ + H2O

salicylate degradation IV :
gentisyl-CoA + H2O → gentisate + coenzyme A + H+

3,3'-thiodipropanoate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+

Not in pathways:
a 1-acyl 2-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-β-D-galactosyl-sn-glycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
gentisate + H+ = CO2 + benzene-1,4-diol

Not in pathways:
a monocarboxylic-acid-amide + H2O = a monocarboxylate + ammonium

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an unknown oxidized electron acceptor + H2O = a carboxylate + an unknown reduced electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

This compound has been characterized as an alternative substrate of the following enzymes: salicylate 1,2-dioxygenase , 2,3-dihydroxybenzoate-AMP ligase , salicylate hydroxylase


References

Dean08: Dean JV, Delaney SP (2008). "Metabolism of salicylic acid in wild-type, ugt74f1 and ugt74f2 glucosyltransferase mutants of Arabidopsis thaliana." Physiol Plant 132(4);417-25. PMID: 18248508

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Wed May 6, 2015, biocyc12.