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MetaCyc Compound: 4-hydroxybenzoate

Synonyms: p-hydroxybenzoate

Superclasses: an aromatic compound

Chemical Formula: C7H5O3

Molecular Weight: 137.12 Daltons

Monoisotopic Molecular Weight: 138.0316940589 Daltons

4-hydroxybenzoate compound structure

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

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

InChIKey: InChIKey=FJKROLUGYXJWQN-UHFFFAOYSA-M

Unification Links: CAS:99-96-7, ChEBI:30763, ChemSpider:132, DrugBank:DB04242, HMDB:HMDB00500, IAF1260:34069, KEGG:C00156, MetaboLights:MTBLC17879, PubChem:135

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

Reactions known to consume the compound:

4-chlorobenzoate degradation , 4-hydroxymandelate degradation , 4-methylphenol degradation to protocatechuate :
4-hydroxybenzoate + NADPH + oxygen + H+ → protocatechuate + NADP+ + H2O

4-coumarate degradation (anaerobic) , phenol degradation II (anaerobic) :
4-hydroxybenzoate + ATP + coenzyme A → 4-hydroxybenzoyl-CoA + AMP + diphosphate

plastoquinol-9 biosynthesis II , ubiquinol-9 biosynthesis (eukaryotic) , ubiquinol-9 biosynthesis (prokaryotic) :
all-trans-nonaprenyl diphosphate + 4-hydroxybenzoate → 3-nonaprenyl-4-hydroxybenzoate + diphosphate

shikonin biosynthesis :
geranyl diphosphate + 4-hydroxybenzoate → 3-geranyl-4-hydroxybenzoate + diphosphate

superpathway of ubiquinol-6 biosynthesis (eukaryotic) , ubiquinol-6 biosynthesis from 4-hydroxybenzoate (eukaryotic) :
all-trans-hexaprenyl diphosphate + 4-hydroxybenzoate → 3-hexaprenyl-4-hydroxybenzoate + diphosphate

tetrahydromethanopterin biosynthesis :
4-hydroxybenzoate + 5-phospho-α-D-ribose 1-diphosphate + H+ → 4-(β-D-ribofuranosyl)hydroxybenzene 5'-phosphate + CO2 + diphosphate

ubiquinol-10 biosynthesis (eukaryotic) , ubiquinol-10 biosynthesis (prokaryotic) :
all-trans-decaprenyl diphosphate + 4-hydroxybenzoate → 3-decaprenyl-4-hydroxybenzoate + diphosphate

ubiquinol-7 biosynthesis (eukaryotic) , ubiquinol-7 biosynthesis (prokaryotic) :
all-trans-heptaprenyl diphosphate + 4-hydroxybenzoate → 3-heptaprenyl-4-hydroxybenzoate + diphosphate

ubiquinol-8 biosynthesis (eukaryotic) , ubiquinol-8 biosynthesis (prokaryotic) :
all-trans-octaprenyl diphosphate + 4-hydroxybenzoate → 3-octaprenyl-4-hydroxybenzoate + diphosphate

Not in pathways:
4-hydroxybenzoate + NAD(P)H + oxygen + H+ → protocatechuate + NAD(P)+ + H2O
4-hydroxybenzoate + NAD(P)H + oxygen + 2 H+ → CO2 + benzene-1,4-diol + NAD(P)+ + H2O
4-hydroxybenzoate + L-glutamate + ATP → N-(4-hydroxybenzoyl)-L-glutamate + AMP + diphosphate + H+

Reactions known to produce the compound:

4-chlorobenzoate degradation , 4-hydroxybenzoate biosynthesis I (eukaryotes) , 4-hydroxybenzoate biosynthesis V :
4-hydroxybenzoyl-CoA + H2O → 4-hydroxybenzoate + coenzyme A + H+

4-coumarate degradation (anaerobic) :
4-hydroxybenzaldehyde + NAD(P)+ + H2O → 4-hydroxybenzoate + NAD(P)H + 2 H+

4-hydroxybenzoate biosynthesis II (microbes) , tetrahydromethanopterin biosynthesis , ubiquinol-8 biosynthesis (eukaryotic) :
chorismate → 4-hydroxybenzoate + pyruvate

4-hydroxybenzoate biosynthesis IV :
4-hydroxybenzaldehyde + NAD+ + H2O → 4-hydroxybenzoate + NADH + 2 H+

4-hydroxymandelate degradation :
4-hydroxybenzaldehyde + NAD+ + H2O → 4-hydroxybenzoate + NADH + 2 H+
4-hydroxybenzaldehyde + NADP+ + H2O → 4-hydroxybenzoate + NADPH + 2 H+

4-methylphenol degradation to protocatechuate :
4-hydroxybenzaldehyde + NADP+ + H2O → 4-hydroxybenzoate + NADPH + 2 H+

cyanidin 3,7-diglucoside polyacylation biosynthesis :
cyanidin 3-O-glucoside-7-O-(6-O-(p-hydroxybenzoyl)-glucoside) + 1-O-4-hydroxybenzoyl-β-D-glucose → cyanidin 3-O-glucoside-7-O-(6-O-(4-O-(glucosyl)-oxybenzoyl)-glucoside) + 4-hydroxybenzoate + H+

cyanidin diglucoside biosynthesis (acyl-glucose dependent) :
cyanidin-3-O-β-D-glucoside + 1-O-4-hydroxybenzoyl-β-D-glucose → cyanidin 3,7-di-O-β-D-glucoside + 4-hydroxybenzoate

violdelphin biosynthesis :
delphinidin 3-O-rutinoside + 1-O-4-hydroxybenzoyl-β-D-glucose → delphinidin 3-O-rutinoside-7-O-glucoside + 4-hydroxybenzoate + H+
delphinidin 3-O-rutinoside-7-O-(6-O-(p-hydroxybenzoyl)-glucoside) + 1-O-4-hydroxybenzoyl-β-D-glucose → delphinidin 3-O-rutinoside-7-O-(6-O-(4-O-(glucosyl)-oxybenzoyl)-glucoside) + 4-hydroxybenzoate + H+

Not in pathways:
2',4'-dihydroxyacetophenone + oxygen → formate + 4-hydroxybenzoate + 2 H+
4-methoxybenzoate + an reduced unknown electron acceptor + oxygen → 4-hydroxybenzoate + formaldehyde + an oxidized unknown electron acceptor + H2O
benzoate + NADPH + oxygen + H+4-hydroxybenzoate + NADP+ + H2O
4-hydroxybenzoate 1-phenylethylidene + H2O → 4-hydroxybenzoate + acetophenone hydrazone + H+

Reactions known to both consume and produce the compound:

phenol degradation II (anaerobic) :
phenyl phosphate + CO2 + H2O ↔ 4-hydroxybenzoate + phosphate + H+

In Reactions of unknown directionality:

Not in pathways:
4-chlorobenzoate + H2O = chloride + 4-hydroxybenzoate + H+
4-hydroxybenzoate + ATP + H+ = 4-hydroxybenzoyl-adenylate + diphosphate
UDP-α-D-glucose + 4-hydroxybenzoate = 4-(β-D-glucosyloxy)benzoate + UDP + H+
an isoprenoid diphosphate + 4-hydroxybenzoate = a 4-hydroxy-3-polyprenylbenzoate + diphosphate
4-hydroxybenzoate + H+ = CO2 + phenol

In Transport reactions:
4-hydroxybenzoate[cytosol] + H+[periplasm]4-hydroxybenzoate[periplasm] + H+[cytosol]

Enzymes inhibited by 4-hydroxybenzoate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: chorismate lyase [Holden02, Comment 1], hydroquinone 1,2-dioxygenase [Moonen08]

This compound has been characterized as an alternative substrate of the following enzymes: 6-hydroxynicotinate 3-monooxygenase, ATP:protocatechuate adenylyltransferase, 2,5-DHBA UDP-glucosyltransferase


References

Holden02: Holden MJ, Mayhew MP, Gallagher DT, Vilker VL (2002). "Chorismate lyase: kinetics and engineering for stability." Biochim Biophys Acta 1594(1);160-7. PMID: 11825618

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

Moonen08: Moonen MJ, Synowsky SA, van den Berg WA, Westphal AH, Heck AJ, van den Heuvel RH, Fraaije MW, van Berkel WJ (2008). "Hydroquinone dioxygenase from pseudomonas fluorescens ACB: a novel member of the family of nonheme-iron(II)-dependent dioxygenases." J Bacteriol 190(15);5199-209. PMID: 18502867

Siebert94: Siebert M, Severin K, Heide L (1994). "Formation of 4-hydroxybenzoate in Escherichia coli: characterization of the ubiC gene and its encoded enzyme chorismate pyruvate-lyase." Microbiology 1994;140 ( Pt 4);897-904. PMID: 8012607


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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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