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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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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

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-phenylpropionate degradation :
3-hydroxybenzoyl-CoA + H+ + oxygen → gentisate + coenzyme A

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

dimethylsulfoniopropionate 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:
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → 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+
a 1-lysophosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
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


a monocarboxylic-acid-amide + H2O = a monocarboxylate + ammonium


eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
an aldehyde + pyrroloquinoline quinone + H2O = a carboxylate + pyrroloquinoline quinol + H+
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 oxidized electron acceptor + H2O = a carboxylate + a 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


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 18.5 on Thu Nov 27, 2014, BIOCYC13B.