Ligand ubiquinone

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Basic Ligand Information

Molecular Structure
Picture of ubiquinone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C14H18O4
ubiquinone
SOECUQMRSRVZQQ-UHFFFAOYSA-N
Synonyms:
1-ubiquinone, 2,3-dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone, 2,3-dimethoxy-5-methyl-6-isoprenyl-1,4-benzoquinone, 6-isoprenylubiquinone, coenzyme Q1, oxidized coenzyme Q1, ubiquinone-1, ubiquinone 1, ubiquinone Q1
Pathway Source
Pathways


Show all pahtways known for Show all BRENDA pathways known for ubiquinone

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (49 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(S)-malate + ubiquinone = oxaloacetate + ubiquinol
show the reaction diagram
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choline + coenzyme Q1 = betaine aldehyde + reduced coenzyme Q1
show the reaction diagram
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D-fructose + ubiquinone = 5-dehydro-D-fructose + ubiquinol
show the reaction diagram
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(S)-2-hydroxyglutarate + ubiquinone = 2-oxoglutarate + ubiquinol
show the reaction diagram
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phenylacetyl-CoA + H2O + ubiquinone = phenylglyoxylyl-CoA + ubiquinol
show the reaction diagram
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caffeine + ubiquinone + H2O = 1,3,7-trimethylurate + ubiquinol
show the reaction diagram
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pyruvate + ubiquinone + H2O = acetate + CO2 + ubiquinol
show the reaction diagram
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acetaldehyde + ubiquinone = acetate + ubiquinol
show the reaction diagram
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CO + ubiquinone + H2O = CO2 + ubiquinol
show the reaction diagram
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(S)-dihydroorotate + ubiquinone = orotate + ubiquinol
show the reaction diagram
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protoporphyrinogen IX + 3 ubiquinone = protoporphyrin IX + 3 ubiquinol
show the reaction diagram
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D-Pro + H2O + coenzyme Q1 = ?
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NADH + H+ + ubiquinone = NAD+ + ubiquinone
show the reaction diagram
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NADH + H+ + ubiquinone = NAD+ + ubiquinol
show the reaction diagram
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nitrite + ubiquinone + H2O = nitrate + ubiquinol
show the reaction diagram
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ubiquinone + NAD(P)H = ubiquinol + NAD(P)+
show the reaction diagram
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sulfide + ubiquinone-1 = sulfur + ubiquinol-1
show the reaction diagram
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2 thiosulfate + ubiquinone = tetrathionate + ubiquinol
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetaldehyde + ubiquinol = ethanol + ubiquinone
show the reaction diagram
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2 O2 + ubiquinol = 2 superoxide + ubiquinone + 2 H+
show the reaction diagram
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NADH + H+ + ubiquinone = NAD+ + ubiquinone
show the reaction diagram
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ubiquinol + O2 + H+[side 1] = ubiquinone + H2O + H+[side 2]
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (190 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ubiquinone-1 + NADPH = ?
show the reaction diagram
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D-lactate + ubiquinone = pyruvate + ubiquinol
show the reaction diagram
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D-lactate + ubiquinone 1 = pyruvate + reduced ubiquinone 1
show the reaction diagram
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L-2-hydroxyglutarate + ubiquinone-1 = 2-oxoglutarate + ubiquinol-1
show the reaction diagram
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D-glucose + coenzyme Q1 = D-glucono-1,5-lactone + reduced coenzyme Q1
show the reaction diagram
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choline + coenzyme Q1 = betaine aldehyde + reduced coenzyme Q1
show the reaction diagram
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D-fructose + ubiquinone = 5-dehydro-D-fructose + ubiquinol
show the reaction diagram
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cellobiose + ubiquinone = cellobiono-1,5-lactone + reduced ubiquinone
show the reaction diagram
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(S)-2-hydroxyglutarate + ubiquinone = 2-oxoglutarate + ubiquinol
show the reaction diagram
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D-gluconate + coenzyme Q1 = 2-oxogluconate + ?
show the reaction diagram
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phenylacetyl-CoA + H2O + ubiquinone = phenylglyoxylyl-CoA + ubiquinol
show the reaction diagram
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caffeine + ubiquinone + H2O = 1,3,7-trimethylurate + ubiquinol
show the reaction diagram
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pyruvate + ubiquinone + H2O = acetate + CO2 + ubiquinol
show the reaction diagram
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acetaldehyde + ubiquinone = acetate + ubiquinol
show the reaction diagram
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protoporphyrinogen IX + 3 ubiquinone = protoporphyrin IX + 3 ubiquinol
show the reaction diagram
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succinate + ubiquinone = fumarate + ubiquinol
show the reaction diagram
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N6-(2-isopentenyl)adenine + coenzyme Q1 = adenine + 3-methylbut-2-enal + reduced coenzyme Q1
show the reaction diagram
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L-proline + coenzyme Q1 + H2O = DELTA1-pyrroline-5-carboxylate + reduced coenzyme Q1
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nitrite + ubiquinone + H2O = nitrate + ubiquinol
show the reaction diagram
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ubiquinone + NAD(P)H = ubiquinol + NAD(P)+
show the reaction diagram
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2 thiosulfate + ubiquinone = tetrathionate + ubiquinol
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (41 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ubiquinol-1 + O2 = ubiquinone-1 + H2O
show the reaction diagram
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2 O2 + ubiquinol = 2 superoxide + ubiquinone + 2 H+
show the reaction diagram
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nicotinamide riboside + reduced coenzyme Q1 = dihydronicotinamide riboside + coenzyme Q1
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ubiquinol-1 + H2O2 = ubiquinone-1 + H2O
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electron-transferring flavoprotein + hydroquinone electron transferring flavoprotein + ubiquinol = semiquinone electron transferring flavoprotein + ubiquinone
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NADH + H+ + ubiquinone = NAD+ + ubiquinone
show the reaction diagram
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nitrate + ubiquinol = nitrite + ubiquinone + H2O
show the reaction diagram
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Enzyme Cofactor/Cosubstrate (29 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
possible physiological acceptor
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the mitochondrial enzyme requires oxidized ubiquinone, CoQ
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coenzyme Q1 is electron acceptor for PRODH/POX, which passes electrons directly to coenzyme Q1 (CoQ1) RODH/POX binds directly to CoQ1 without the formation of a tertiary complex. The transfer of electrons from proline to CoQ1 by PRODH/POX is dependent on downstream electron transfer from CoQ1 to Complexes III and IV
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tightly bound ubiquinone cofactor, which becomes oxidized to hydroquinone and is regenerated by the electron transport chain and O2PDI contains four transmembrane helices that surround the bound ubiquinone cofactor, overview
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enzyme contains approximately one bound ubiquinone
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
reduction of 2,6-dichlorophenol indophenol by solubilized enzyme is activated significantly by addition of the quinones decylubiquinone, duroquinone, 2-methyl-1,4-naphthoquinone (vitamin K3), ubiquinone-0 and ubiquinone-1. Optimal activation is observed with ubiquinone-1
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slight increase in activity might be due to formation of ubiquinol in the assay system
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Inhibitor in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
product inhibition, an excess amount of ubiquinol-2 is unable to suppress product inhibition with ubiquinone-1 therefore, the inhibition mode may not be competitive
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product inhibition, mixed-type
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3D Structure of Enzyme-Ligand-Complex (PDB) (25 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (85 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
76.3
-
using ethanol as cosubstrate, pH and temperature not specified in the publication
-999
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at saturating concentration of dihydroorotate
6.15
-
at saturating concentration of dihydroorotate
0.19
-
at pH 7.5 and 25°C
123.1
-
pH 6.5, recombinant enzyme
6.4
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pH 8.5, 60°C
0.000007
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at pH 8.0 and 30°C

KM Value (106 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.015
0.017
Km depending on enzyme form
0.015
-
pH 7.4, 25°C
0.047
-
using ethanol as cosubstrate, pH and temperature not specified in the publication
0.06
-
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0.11
-
-
0.0517
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using N-benzyl dihydronicotinamide as cosubstrate, at 25°C, in 50 mM Tris-HCl, pH 8.5
0.0131
-
at saturating concentration of dihydroorotate
0.0082
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pH 8.0, 37°C
0.0082
-
in 50 mM sodium-phosphate buffer (pH 8.0), at 37°C
0.124
-
at pH 7.5 and 25°C
0.12
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pH 8.5, 60°C
0.0152
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in 50 mM sodium phosphate buffer (pH 6.0) and 1 mM EDTA, temperature not specified in the publication
0.0156
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at pH 8.5 and 37°C
0.0028
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at pH 8.0 and 30°C

References & Links

Links to other databases for ubiquinone

ChEBI
PubChem
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PubChem