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MetaCyc Compound: benzene-1,4-diol

Synonyms: 1,4-benzenediol, hydroquinol, hydroquinone

Superclasses: an alcohol a diol a benzenediol
an aromatic compound a benzenediol
an aromatic compound a 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): 12.246721 Inferred 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 → (2E,4Z)-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 , phosphate utilization in cell wall regeneration :
a phosphate monoester + H2O → an alcohol + phosphate

Not in pathways:
an organic hydroperoxide + NADH + H+an alcohol + NAD+ + H2O
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

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+
trans-cinnamoyl-β-D-glucoside + an alcohol = β-D-glucopyranose + 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

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

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: 4-hydroxyphenylacetate 3-monooxygenase , 1,2,4-trihydroxybenzene 1,2-dioxygenase


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."


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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 19.0 on Tue Aug 4, 2015, biocyc14.