Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
twitter

MetaCyc Compound: 3-hydroxybenzoate

Synonyms: 3-hydroxybenzoic acid, m-hydroxybenzoate

Superclasses: an acidall carboxy acidsa carboxylatean aromatic carboxylatea benzoate
an aromatic compoundan aromatic carboxylatea benzoate

Chemical Formula: C7H5O3

Molecular Weight: 137.12 Daltons

Monoisotopic Molecular Weight: 138.0316940589 Daltons

3-hydroxybenzoate compound structure

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

InChI: InChI=1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10)/p-1

InChIKey: InChIKey=IJFXRHURBJZNAO-UHFFFAOYSA-M

Unification Links: ChEBI:16193, ChemSpider:3186867, HMDB:HMDB02466, KEGG:C00587, PubChem:54675842

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -41.486458Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

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

m-cresol degradation :
3-hydroxybenzoate + NADH + oxygen + H+ → gentisate + NAD+ + H2O
3-hydroxybenzoate + NADPH + oxygen + H+ → protocatechuate + NADP+ + H2O

tetrahydroxyxanthone biosynthesis (from 3-hydroxybenzoate) :
3-hydroxybenzoate + ATP + coenzyme A → 3-hydroxybenzoyl-CoA + AMP + diphosphate

Not in pathways:
3-hydroxybenzoate + an reduced unknown electron acceptor + oxygen → 2,3-dihydroxybenzoate + an oxidized unknown electron acceptor + H2O

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

Not in pathways:
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

3-chlorobenzoate degradation III (via gentisate) :
3-chlorobenzoate + H2O → 3-hydroxybenzoate + chloride + H+

m-cresol degradation , patulin biosynthesis :
3-hydroxybenzaldehyde + NADP+ + H2O → 3-hydroxybenzoate + NADPH + 2 H+

Not in pathways:
3-hydroxybenzoyl-CoA + H2O → 3-hydroxybenzoate + coenzyme A + H+

Not in pathways:
an aryl aldehyde + oxygen + H2O → an aromatic carboxylate + hydrogen peroxide

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[periplasm] + H2O[periplasm]a carboxylate[periplasm] + sn-glycero-3-phosphocholine[periplasm] + H+[periplasm]
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 acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-O-(β-D-galactopyranosyl)-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 ↔ D-erythro-sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
chorismate = 3-hydroxybenzoate + pyruvate

Not in pathways:
AMP + an aryl aldehyde + NADP+ + diphosphate = ATP + an aromatic carboxylate + NADPH
an aryl aldehyde + NAD+ + H2O = an aromatic carboxylate + NADH + H+

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + sn-glycero-3-phosphocholine[periplasm] + H+[periplasm]
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[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]
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 unknown electron acceptor + H2O = a carboxylate + an reduced unknown 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 [iron-sulfur] cluster + H2O = a carboxylate + 2 a reduced ferredoxin [iron-sulfur] cluster + 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

Enzymes inhibited by 3-hydroxybenzoate, sorted by the type of inhibition, are:

Inhibitor (Noncompetitive) of: p-hydroxybenzoate hydroxylase [Hosokawa66] Inhibitor (Mechanism unknown) of: 3-hydroxyanthranilate 3,4-dioxygenase [Malherbe94]

This compound has been characterized as an alternative substrate of the following enzymes: 3-hydroxy-4-methylanthranilate adenylyltransferase, ATP:protocatechuate adenylyltransferase


References

Hosokawa66: Hosokawa K, Stanier RY (1966). "Crystallization and properties of p-hydroxybenzoate hydroxylase from Pseudomonas putida." J Biol Chem 241(10);2453-60. PMID: 4380381

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

Malherbe94: Malherbe P, Kohler C, Da Prada M, Lang G, Kiefer V, Schwarcz R, Lahm HW, Cesura AM (1994). "Molecular cloning and functional expression of human 3-hydroxyanthranilic-acid dioxygenase." J Biol Chem 269(19);13792-7. PMID: 7514594


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 19.5 on Thu Feb 11, 2016, BIOCYC11A.