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MetaCyc Compound: benzene-1,4-diol

Synonyms: 1,4-benzenediol, hydroquinol, hydroquinone

Superclasses: an alcohola diola benzenediol
an aromatic compounda benzenediol
an aromatic compounda quinol

Chemical Formula: C6H6O2

Molecular Weight: 110.11 Daltons

Monoisotopic Molecular Weight: 110.03677943679999 Daltons

benzene-1,4-diol compound structure

SMILES: C1(=CC(O)=CC=C(O)1)

InChI: InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H

InChIKey: InChIKey=QIGBRXMKCJKVMJ-UHFFFAOYSA-N

Unification Links: CAS:123-31-9, ChEBI:17594, ChemSpider:764, HMDB:HMDB02434, IAF1260:35259, KEGG:C00530, MetaboLights:MTBLC17594, PubChem:785

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 12.246721Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

4-aminophenol degradation :
benzene-1,4-diol → 1,2,4-benzenetriol

4-hydroxyacetophenone degradation , 4-nitrophenol degradation I :
benzene-1,4-diol + oxygen → (2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate + H+

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

Reactions known to produce the compound:

4-aminophenol degradation :
4-aminophenol + H2O + H+benzene-1,4-diol + ammonium

4-hydroxyacetophenone degradation :
4-hydroxyphenylacetate + H2O → benzene-1,4-diol + acetate

4-nitrophenol degradation I :
1,4-benzoquinone + NADPH + H+benzene-1,4-diol + NADP+

echinenone and zeaxanthin biosynthesis (Synechocystis) :
all-trans-β-carotene + 2 1,4-benzoquinone + H2O → echinenone + 2 benzene-1,4-diol

Not in pathways:
arbutin-6-phosphate + H2O → β-D-glucose 6-phosphate + benzene-1,4-diol
4-hydroxybenzoate + NAD(P)H + oxygen + 2 H+ → CO2 + benzene-1,4-diol + NAD(P)+ + H2O

phenylacetate degradation II (anaerobic) :
phenylacetyl-CoA + 2 a quinone + H2O → 2 a quinol + phenylglyoxylyl-CoA

quinate degradation I :
L-quinate + a quinone → 3-dehydroquinate + a quinol

shikimate degradation I :
shikimate + a quinone → 3-dehydroshikimate + a quinol

thiosulfate oxidation II (via tetrathionate) :
2 thiosulfate + a quinone → tetrathionate + a quinol

Not in pathways:
a cyclic alcohol + a quinone → a cyclic ketone + a quinol

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 :
a phosphate monoester + H2O → an alcohol + phosphate

Not in pathways:
an organic hydroperoxide + NADH + H+an alcohol + NAD+ + H2O
a 6-phospho-β-D-galactoside + H2O → D-galactopyranose 6-phosphate + an alcohol
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

In Reactions of unknown directionality:

Not in pathways:
gentisate + H+ = CO2 + benzene-1,4-diol
UDP-α-D-glucose + benzene-1,4-diol = arbutin + UDP + H+
chloride + benzene-1,4-diol + glutathione disulfide + H+ = chlorohydroquinone + 2 glutathione

Not in pathways:
1-(β-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone + H+ = a quinol + 1-(β-D ribofuranosyl)nicotinamide

Not in pathways:
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+
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
trans-cinnamoyl-β-D-glucoside + an alcohol = alkyl cinnamate + D-glucopyranose
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

In Transport reactions:
benzene-1,4-diol[cytosol]benzene-1,4-diol[periplasm]

Enzymes inhibited by benzene-1,4-diol, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: ethylnitronate monooxygenase [Kido78]

This compound has been characterized as an alternative substrate of the following enzymes: 1,2,4-trihydroxybenzene 1,2-dioxygenase, 4-hydroxyphenylacetate 3-monooxygenase


References

Kido78: Kido T, Soda K (1978). "Properties of 2-nitropropane dioxygenase of Hansenula mrakii. Formation and participation of superoxide." J Biol Chem 253(1);226-32. PMID: 201619

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


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 Pathway Tools version 19.5 (software by SRI International) on Sat Feb 6, 2016, biocyc14.