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discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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MetaCyc Compound: benzene-1,4-diol

Synonyms: 1,4-benzenediol, hydroquinol, hydroquinone

Superclasses: a redox electron carrier Membrane-Electron-Carriers an electron-transfer-related quinol
an alcohol a diol a benzenediol
an aromatic compound a benzenediol
an aromatic compound a quinol an electron-transfer-related quinol

Chemical Formula: C6H6O2

Molecular Weight: 110.11 Daltons

Monoisotopic Molecular Weight: 110.03677943679999 Daltons

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+

methane oxidation to methanol II :
methane + an electron-transfer-related quinol + oxygen → methanol + an electron-transfer-related quinone + H2O

TCA cycle VI (obligate autotrophs) :
succinate[in] + an electron-transfer-related quinone[CCO-OUT-CCO-IN] ← fumarate[in] + an electron-transfer-related quinol[CCO-OUT-CCO-IN]

Not in pathways:
2 an oxidized c-type cytochrome[out] + an electron-transfer-related quinol → 2 a reduced c-type cytochrome[out] + an electron-transfer-related quinone + 2 H+[in]


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

Reactions known to produce the compound:

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

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

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

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

(5R)-carbapenem carboxylate biosynthesis , citrulline biosynthesis , L-Nδ-acetylornithine biosynthesis , proline degradation :
L-proline + an electron-transfer-related quinone[inner membrane] → (S)-1-pyrroline-5-carboxylate + an electron-transfer-related quinol[inner membrane] + H+

4-hydroxymandelate degradation :
(S)-4-hydroxymandelate + an electron-transfer-related quinone → 2-(4-hydroxyphenyl)-2-oxoacetate + an electron-transfer-related quinol

alanine degradation I :
D-alanine + an electron-transfer-related quinone[inner membrane] + H2O → ammonium + pyruvate + an electron-transfer-related quinol[inner membrane]

sulfide oxidation I (sulfide-quinone reductase) :
hydrogen sulfide + an electron-transfer-related quinone → intracellular S0 + an electron-transfer-related quinol

TCA cycle IV (2-oxoglutarate decarboxylase) , TCA cycle V (2-oxoglutarate:ferredoxin oxidoreductase) , TCA cycle VII (acetate-producers) :
succinate[in] + an electron-transfer-related quinone[CCO-OUT-CCO-IN] → fumarate[in] + an electron-transfer-related quinol[CCO-OUT-CCO-IN]

trans-4-hydroxy-L-proline degradation I :
trans-4-hydroxy-L-proline[in] + an electron-transfer-related quinone → pyrroline-hydroxy-carboxylate[in] + an electron-transfer-related quinol + H+[in]

trans-lycopene biosynthesis II (plants) :
9,9'-di-cis-ζ-carotene + an electron-transfer-related quinone → 7,9,9'-cis-neurosporene + an electron-transfer-related quinol
7,9,9'-cis-neurosporene + an electron-transfer-related quinone → prolycopene + an electron-transfer-related quinol


sn-glycerol 3-phosphate[in] + an electron-transfer-related quinone[CCO-OUT-CCO-IN] → dihydroxyacetone phosphate[in] + an electron-transfer-related quinol[CCO-OUT-CCO-IN]
D-glucopyranose[out] + an electron-transfer-related quinone + 2 H+[in] → D-glucono-1,5-lactone[out] + an electron-transfer-related quinol + 2 H+[out]
a D-amino acid[in] + an electron-transfer-related quinone[CCO-OUT-CCO-IN] + H2O[in] → a 2-oxo carboxylate[in] + ammonium[in] + an electron-transfer-related quinol[CCO-OUT-CCO-IN]
NADPH + an electron-transfer-related quinone + H+ → NADP+ + an electron-transfer-related quinol
(S)-dihydroorotate + an electron-transfer-related quinone[inner membrane] → orotate + an electron-transfer-related quinol[inner membrane]

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

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

TCA cycle I (prokaryotic) , TCA cycle VII (acetate-producers) :
(S)-malate + a quinone → oxaloacetate + a quinol

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


a cyclic alcohol + a quinone → a cyclic ketone + a quinol
a quinone + NAD(P)H + H+a quinol + NAD(P)+

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:

nitrate reduction I (denitrification) , nitrate reduction VII (denitrification) :
nitrate[in] + an electron-transfer-related quinol ↔ nitrite[in] + an electron-transfer-related quinone + H2O[in]

In Reactions of unknown directionality:

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


an oxidized coenzyme F420 + an electron-transfer-related quinol = a reduced coenzyme F420 + an electron-transfer-related quinone
an (R)-2-hydroxyacid + an electron-transfer-related quinone = a 2-oxo acid + an electron-transfer-related quinol
NADH + an electron-transfer-related quinone + H+ = NAD+ + an electron-transfer-related quinol
formate + an electron-transfer-related quinone + H+ = CO2 + an electron-transfer-related quinol
9,9'-di-cis-ζ-carotene + 2 an electron-transfer-related quinone = prolycopene + 2 an electron-transfer-related quinol


1-(β-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone + H+ = a quinol + 1-(β-D ribofuranosyl)nicotinamide
phenylacetyl-CoA + 2 a quinone + H2O = 2 a quinol + phenylglyoxylyl-CoA


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

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

In Redox half-reactions:
an electron-transfer-related quinone + 2 H+[in] + 2 e-an electron-transfer-related quinol

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

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


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 SRI International Pathway Tools version 18.5 on Sun Dec 21, 2014, BIOCYC14A.