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MetaCyc Compound: protocatechuate

Synonyms: 4-carboxy-1,2-dihydroxybenzene, catechol-4-carboxylic acid, 4,5-dihydroxybenzoic acid, benzoic acid, 3,4-dihydroxy-, 3,4-DHBA, protocatehuic acid, 3,4-dihydroxybenzoic acid, protocatechuic acid, 3,4-dihydroxybenzoate, 3,4-dihydrobenzoic acid, Pca

Superclasses: an acid all carboxy acids a carboxylate an aromatic carboxylate
an alcohol a diol a benzenediol a catechol
an aromatic compound a benzenediol a catechol
an aromatic compound an aromatic carboxylate

Summary:
4-Carboxy-1,2-dihydroxybenzene

Citations: [Lim02]

Chemical Formula: C7H5O4

Molecular Weight: 153.11 Daltons

Monoisotopic Molecular Weight: 154.026608681 Daltons

protocatechuate compound structure

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

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

InChIKey: InChIKey=YQUVCSBJEUQKSH-UHFFFAOYSA-M

Unification Links: ChEBI:36241 , ChemSpider:3353991 , DrugBank:DB03946 , HMDB:HMDB01856 , KEGG:C00230 , KNApSAcK:C00002668 , PubChem:54675866

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

Reactions known to consume the compound:

petrobactin biosynthesis :
protocatechuate + ATP + H+ → 3,4-dihydroxybenzoate-adenylate + diphosphate

protocatechuate degradation I (meta-cleavage pathway) :
protocatechuate + oxygen → 2-hydroxy-4-carboxymuconate-6-semialdehyde + H+

protocatechuate degradation II (ortho-cleavage pathway) :
protocatechuate + oxygen → 3-carboxy-cis,cis-muconate + 2 H+

protocatechuate degradation III (para-cleavage pathway) :
protocatechuate + oxygen → (2Z,4Z)-2-hydroxy-5-carboxymuconate-6-semialdehyde + H+

ubiquinol-6 bypass biosynthesis (eukaryotic) :
protocatechuate + all-trans-hexaprenyl diphosphate → 3,4-dihydroxy-5-all-trans-hexaprenylbenzoate + diphosphate

Not in pathways:
a catechol + S-adenosyl-L-methionine → a guaiacol + S-adenosyl-L-homocysteine + 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

Not in pathways:
4 a benzenediol + oxygen → 4 a benzosemiquinone + 2 H2O

Reactions known to produce the compound:

3-chlorobenzoate degradation II (via protocatechuate) :
3-chlorobenzoate-cis-3,4-diol → protocatechuate + chloride + H+

4-chlorobenzoate degradation , 4-hydroxymandelate degradation , toluene degradation to protocatechuate (via p-cresol) :
4-hydroxybenzoate + NADPH + oxygen + H+protocatechuate + NADP+ + H2O

4-nitrobenzoate degradation :
4-hydroxylaminobenzoate + H+ + H2O → protocatechuate + ammonium

4-toluenecarboxylate degradation :
(3S,4R)-3,4-dihydroxycyclohexa-1,5-diene-1,4-dicarboxylate + NAD+ + H2O → protocatechuate + hydrogen carbonate + NADH + H+

4-toluenesulfonate degradation I :
4-sulfobenzoate + NADH + oxygen → sulfite + protocatechuate + NAD+

m-cresol degradation :
3-hydroxybenzoate + NADPH + oxygen + H+protocatechuate + NADP+ + H2O

petrobactin biosynthesis , quinate degradation I , quinate degradation II , shikimate degradation I , shikimate degradation II :
3-dehydroshikimate → protocatechuate + H2O

phthalate degradation :
3,4-dihydroxyphthalate + H+ → CO2 + protocatechuate

rutin degradation :
2-protocatechuoylphloroglucinolcarboxylate + H2O → phloroglucinol carboxylate + protocatechuate + H+

vanillin and vanillate degradation I :
vanillate + a tetrahydrofolate → protocatechuate + an N5-methyl-tetrahydrofolate

vanillin and vanillate degradation II :
vanillate + NADH + oxygen + H+protocatechuate + formaldehyde + NAD+ + H2O

Not in pathways:
protocatechualdehyde + oxygen + H2O → protocatechuate + hydrogen peroxide + H+
4-hydroxybenzoate + NAD(P)H + oxygen + H+protocatechuate + NAD(P)+ + H2O

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+

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:
4,5-dihydroxyphthalate + H+ = CO2 + protocatechuate
(3S,4R)-3,4-dihydroxycyclohexa-1,5-diene-1,4-dicarboxylate + NAD+ = protocatechuate + CO2 + NADH
protocatechuate + H+ = CO2 + catechol

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+

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

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

Inhibitor (Noncompetitive) of: p-hydroxybenzoate hydroxylase [Hosokawa66]

This compound has been characterized as an alternative substrate of the following enzymes: 2-amino-5-chlorophenol 1,6-dioxygenase , 2,5-DHBA UDP-glucosyltransferase , gallate dioxygenase , catechol O-methyltransferase


References

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

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."

Lim02: Lim EK, Doucet CJ, Li Y, Elias L, Worrall D, Spencer SP, Ross J, Bowles DJ (2002). "The activity of Arabidopsis glycosyltransferases toward salicylic acid, 4-hydroxybenzoic acid, and other benzoates." J Biol Chem 277(1);586-92. PMID: 11641410

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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