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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
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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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

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+


4 a benzenediol + oxygen → 4 a benzosemiquinone + 2 H2O

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


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 II (via protocatechuate) :
3-chlorobenzoate-cis-3,4-diol + NAD+protocatechuate + chloride + NADH

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


an aryl aldehyde + oxygen + H2O → an aromatic carboxylate + hydrogen peroxide

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+


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

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+

phosphate acquisition , phosphate utilization in cell wall regeneration :
a phosphate monoester + H2O ↔ an alcohol + phosphate


an alcohol + NAD+ + H2O ← an organic hydroperoxide + NADH + H+
an α-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a phosphate monoester + H2O → an alcohol + phosphate
RH + a reduced [NADPH-hemoprotein reductase] + oxygen → ROH + an oxidized [NADPH-hemoprotein reductase] + H2O
an oligosaccharide with β-L-arabinopyranose at the non-reducing end + H2O → β-L-arabinopyranose + an alcohol
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acetic ester + H2O → an alcohol + acetate + H+
a reduced thioredoxin + an organic hydroperoxide → an oxidized thioredoxin + an alcohol + H2O
a 6-O-(β-D-xylopyranosyl)-β-D-glucopyranoside + H2O → β-primeverose + an alcohol
an organic molecule + H2O + 2 oxygen → an alcohol + 2 superoxide + 2 H+
an N5-acyl-L-ornithine-ester + H2O → an N5-acyl-L-ornithine + an alcohol
α-L-fucoside + H2O → L-fucopyranose + an alcohol
a 2-deoxy-α-D-glucoside + H2O → 2-deoxy-D-glucose + an alcohol
a 6-phospho-β-D-galactoside + H2O → α-D-galactose 6-phosphate + an alcohol

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


AMP + an aryl aldehyde + NADP+ + diphosphate = ATP + an aromatic carboxylate + NADPH
an aryl aldehyde + NAD+ + H2O = an aromatic carboxylate + NADH + H+


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


an alcohol + 3'-phosphoadenylyl-sulfate = adenosine 3',5'-bisphosphate + an organosulfate + H+
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
an alcohol + NADP+ = an aldehyde + NADPH + H+
trans-cinnamoyl-β-D-glucoside + an alcohol = β-D-glucose + alkyl cinnamate
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
2 protein cysteines + an organic hydroperoxide = a protein disulfide + an alcohol + H2O
an organic molecule + an organic hydroperoxide = 2 an alcohol
an organic molecule + hydrogen peroxide = an alcohol + H2O

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

Inhibitor (Competitive) of: glutamate decarboxylase A [Youngs, 1991, Helmward89] , glutamate decarboxylase B [Youngs, 1991, Helmward89]

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


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

Youngs, 1991: 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


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 Fri Nov 28, 2014, BIOCYC13B.