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MetaCyc Compound: 3-hydroxybenzoate

Synonyms: 3-hydroxybenzoic acid, m-hydroxybenzoate

Superclasses: an acid all carboxy acids a carboxylate an aromatic carboxylate a benzoate
an aromatic compound an aromatic carboxylate a 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 Change Formation (ΔfG in kcal/mol): -41.486458 Inferred 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:
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) :
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[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 β-monogalactosyldiacylglycerol + 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:
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[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 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 + 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

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: 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 19.0 on Mon Aug 31, 2015, BIOCYC14A.