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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: 4-hydroxybenzoate

Synonyms: p-hydroxybenzoate

Superclasses: an aromatic compound

Chemical Formula: C7H5O3

Molecular Weight: 137.12 Daltons

Monoisotopic Molecular Weight: 138.0316940589 Daltons

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 Change Formation (ΔfG in kcal/mol): -41.486458 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

4-chlorobenzoate degradation , 4-hydroxymandelate degradation , toluene degradation to protocatechuate (via p-cresol) :
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 , toluene degradation to protocatechuate (via p-cresol) :
4-hydroxybenzaldehyde + NAD+ + H2O → 4-hydroxybenzoate + NADH + 2 H+

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

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 + a reduced electron acceptor + oxygen → 4-hydroxybenzoate + formaldehyde + an oxidized electron acceptor + H2O
benzoate + NADPH + oxygen + H+4-hydroxybenzoate + NADP+ + H2O

Reactions known to both consume and produce the compound:

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

In Reactions of unknown directionality:

Not in pathways:
4-chlorobenzoate + H2O = chloride + 4-hydroxybenzoate + H+
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+[periplasmic space]4-hydroxybenzoate[periplasmic space] + 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]


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
Page generated by SRI International Pathway Tools version 18.5 on Thu Nov 27, 2014, BIOCYC13B.