Information on EC 1.6.5.3 - NADH:ubiquinone reductase (H+-translocating)

for references in articles please use BRENDA:EC1.6.5.3
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The expected taxonomic range for this enzyme is: Archaea, Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.6.5.3
-
RECOMMENDED NAME
GeneOntology No.
NADH:ubiquinone reductase (H+-translocating)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
NADH + ubiquinone + 6 H+[side 1] = NAD+ + ubiquinol + 7 H+[side 2]
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
aerobic respiration I (cytochrome c)
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aerobic respiration III (alternative oxidase pathway)
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Fe(II) oxidation
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NAD/NADH phosphorylation and dephosphorylation
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NADH to cytochrome bd oxidase electron transfer I
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NADH to cytochrome bo oxidase electron transfer I
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Oxidative phosphorylation
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
NADH:ubiquinone oxidoreductase
A flavoprotein (FMN) containing iron-sulfur clusters. The complex is present in mitochondria and aerobic bacteria. Breakdown of the complex can release EC 1.6.99.3, NADH dehydrogenase. In photosynthetic bacteria, reversed electron transport through this enzyme can reduce NAD+ to NADH.
CAS REGISTRY NUMBER
COMMENTARY hide
9028-04-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Bacillus sp. SR-2-1/1
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Chlamydomonas sp.
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
var. melopepo, zucchini
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Manually annotated by BRENDA team
mutant derivative of strain BW25113 from which the nuo operon is deleted by genomic replacement
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Manually annotated by BRENDA team
GR19N
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
C57/Bl mice
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Manually annotated by BRENDA team
cultivar Samsun
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
T1KH75 i.e. 49 kDa subunit, A0A1D8X822 i.e. PSST subunit
T1KH75 and A0A1D8X822
UniProt
Manually annotated by BRENDA team
Thermus thermophilus HB27 / ATCC BAA-163 / DSM 7039
-
UniProt
Manually annotated by BRENDA team
subunit NqrB
UniProt
Manually annotated by BRENDA team
subunit NqrB
UniProt
Manually annotated by BRENDA team
Vitis vinifera x Vitis vinifera
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Manually annotated by BRENDA team
NUGM, 30-kDa subunit of complex I
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2 ferricyanide + deamino-NADH
2 ferrocyanide + deamino-NAD+ + H+
show the reaction diagram
2 ferricyanide + NADH
2 ferrocyanide + NAD+ + H+
show the reaction diagram
2 ferricyanide + NADPH
2 ferrocyanide + NADP+ + H+
show the reaction diagram
2 ferricytochrome c + NADH
2 ferrocytochrome c + NAD+ + H+
show the reaction diagram
2,3-dimethyl-1,4-naphthoquinone + NADH + H+
2,3-dimethyl-1,4-hydronaphthoquinol + NAD+
show the reaction diagram
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADH + H+
2-methyl-1,4-naphthoquinol + NAD+
show the reaction diagram
amplex red + NADH + O2
resorufin + NAD+ + H2O2
show the reaction diagram
-
the rate of H2O2 formation by complex I strongly depends upon the NAD+/NADH ratio
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-
?
benzoquinone + NADH + H+
benzohydroquinone + NAD+
show the reaction diagram
-
-
-
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?
deamino-NADH + dimethoxy-5-methyl-6-decyl-1,4-benzoquinone
deamino-NAD+ + reduced dimethoxy-5-methyl-6-decyl-1,4-benzoquinone
show the reaction diagram
-
-
-
-
?
deamino-NADH + ubiquinone
deamino-NAD+ + ubiquinol
show the reaction diagram
-
-
-
-
?
deamino-nicotinamide-adeninedinucleotide + n-decylubiquinone
? + n-decylubiquinol
show the reaction diagram
-
-
-
-
?
decyl-ubiquinone + NADH
decyl-ubiquinol + NAD+
show the reaction diagram
decyl-ubiquinone + NADH + H+
decyl-ubiquinol + NAD+
show the reaction diagram
-
-
-
-
?
dihydroethidium + O2
ethidium + H2O2
show the reaction diagram
-
dihydroethidium reduction shows that, upon reducing O2, it produces approximately 20% superoxide and 80% H2O2
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-
?
glutamate
?
show the reaction diagram
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-
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-
?
malate
?
show the reaction diagram
-
-
-
-
?
malate + pyruvate + O2
?
show the reaction diagram
-
-
-
-
?
NADH + 1,1'-carbamoylmethylviologen
NAD+ + reduced 1,1'-carbamoylmethylviologen
show the reaction diagram
-
-
-
-
r
NADH + 2,3-dimethoxy-5-methyl-6-isoprenyl-1,4-benzoquinone
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + 2,3-dimethoxy-5-methyl-6-[(6-methyl-2,3-dihydroimidazo[2,1-b][1,3]thiazol-5-yl)methyl]benzo-1,4-quinone
NAD+ + ?
show the reaction diagram
NADH + 2,3-dimethoxy-5-methyl-6-[(6-methylimidazo[2,1-b][1,3]thiazol-5-yl)methyl]benzo-1,4-quinone
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + 2,3-dimethoxy-5-methyl-6-[(6-phenylimidazo[2,1-b][1,3]thiazol-5-yl)methyl]benzo-1,4-quinone
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + 2-methyl-1,4-naphthoquinone
NAD+ + 2-methyl-1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
NADH + 2-methylnaphthoquinone
NAD+ + ?
show the reaction diagram
NADH + 2-[(2,6-dimethylimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-5,6-dimethoxy-3-methylbenzo-1,4-quinone
NAD+ + ?
show the reaction diagram
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-
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?
NADH + 2-[(2-chloro-6-methylimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-5,6-dimethoxy-3-methylbenzo-1,4-quinone
NAD+ + ?
show the reaction diagram
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?
NADH + 2-[(2-chloro-6-phenylimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-5,6-dimethoxy-3-methylbenzo-1,4-quinone
NAD+ + ?
show the reaction diagram
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?
NADH + 2-[(6-chloro-2,3-dihydroimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-5,6-dimethoxy-3-methylbenzo-1,4-quinone
NAD+ + ?
show the reaction diagram
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?
NADH + 2-[(6-chloro-2-methylimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-5,6-dimethoxy-3-methylbenzo-1,4-quinone
NAD+ + ?
show the reaction diagram
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?
NADH + 2-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-5,6-dimethoxy-3-methylbenzo-1,4-quinone
NAD+ + ?
show the reaction diagram
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?
NADH + 3'-acetyl pyridine adenine dinucleotide
NAD+ + ?
show the reaction diagram
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?
NADH + 6-decyl-ubiquinone
NAD+ + 6-decyl-ubiquinol
show the reaction diagram
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?
NADH + anthraquinone-2,6-disulfonate
NAD+ + ?
show the reaction diagram
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?
NADH + benzoquinone
NAD+ + benzoquinol
show the reaction diagram
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?
NADH + benzoquinone + H+
NAD+ + benzoquinol
show the reaction diagram
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?
NADH + caldariellaquinone
NAD+ + caldariellaquinol
show the reaction diagram
NADH + coenzyme Q0
NAD+ + ?
show the reaction diagram
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?
NADH + coenzyme Q1
NAD+ + ?
show the reaction diagram
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-
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?
NADH + coenzyme Q1 + H+
NAD+ + reduced coenzyme Q1
show the reaction diagram
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?
NADH + coenzyme Q10
?
show the reaction diagram
NADH + coenzyme Q2
NAD+ + ?
show the reaction diagram
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?
NADH + decyl-ubiquinone
NAD+ + decyl-ubiquinol
show the reaction diagram
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?
NADH + decyl-ubiquinone + H+
NAD+ + decyl-ubiquinol
show the reaction diagram
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-
-
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?
NADH + decylubiquinone
NAD+ + decylubiquinol
show the reaction diagram
NADH + decylubiquinone + H+
NAD+ + decylubiquinol
show the reaction diagram
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-
-
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?
NADH + duroquinone
NAD+ + ?
show the reaction diagram
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-
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?
NADH + duroquinone
NAD+ + duroquinol
show the reaction diagram
NADH + FAD
NAD+ + FADH2
show the reaction diagram
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-
-
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?
NADH + Fe(CN)63-
?
show the reaction diagram
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?
NADH + H+ + 1,4-benzoquinone
NAD+ + 1,4-benzoquinol
show the reaction diagram
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-
-
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?
NADH + H+ + 1,4-naphthoquinone
NAD+ + 1,4-naphthoquinol
show the reaction diagram
NADH + H+ + 2,5-dimethyl-1,4-benzoquinone
NAD+ + 2,5-dimethyl-1,4-benzoquinol
show the reaction diagram
-
-
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?
NADH + H+ + 2-methyl-1,4-benzoquinone
NAD+ + 2-methyl-1,4-benzoquinol
show the reaction diagram
-
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?
NADH + H+ + 2-methyl-1,4-naphthoquinone
NAD+ + 2-methyl-1,4-naphthoquinol
show the reaction diagram
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-
-
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?
NADH + H+ + 4-nitroacetophenone
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 4-nitrobenzaldehyde
NAD+ + ?
show the reaction diagram
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-
-
-
?
NADH + H+ + 4-nitrobenzoic acid
NAD+ + ?
show the reaction diagram
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-
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?
NADH + H+ + 5,8-dioxo-1,4-naphthoquinone
NAD+ + 5,8-dioxo-1,4-naphthoquinol
show the reaction diagram
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-
-
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?
NADH + H+ + 5-oxo-1,4-naphthoquinone
NAD+ + 5-oxo-1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + 9,10-phenanthrenequinone
NAD+ + 9,10-phenanthrenequinol
show the reaction diagram
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-
-
-
?
NADH + H+ + adriamycin
NAD+ + ?
show the reaction diagram
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-
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?
NADH + H+ + coenzyme Q1
NAD+ + reduced coenzyme Q1
show the reaction diagram
NADH + H+ + coenzyme Q2
NAD+ + reduced coenzyme Q2
show the reaction diagram
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-
-
-
?
NADH + H+ + decylubiquinone
NAD+ + decylubiquinol
show the reaction diagram
NADH + H+ + duroquinone
NAD+ + duroquinol
show the reaction diagram
NADH + H+ + idebenone
NAD+ + ?
show the reaction diagram
-
studies of ubiquinone reduction by isolated complex I are problematic because the extremely hydrophobic natural substrate, ubiquinone-10, must be substituted with a relatively hydrophilic analogue (such as ubiquinone-1). Hydrophilic ubiquinones are reduced by an additional, non-energy-transducing pathway. Inhibitor-insensitive ubiquinone reduction occurs by a ping-pong type mechanism, catalyzed by the flavin mononucleotide cofactor in the active site for NADH oxidation. Moreover, semiquinones produced at the flavin site initiate redox cycling reactions with molecular oxygen, producing superoxide radicals and hydrogen peroxide. The ubiquinone reactant is regenerated, so the NADH:Q reaction becomes superstoichiometric. Idebenone, an artificial ubiquinone, reacts at the flavin site
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?
NADH + H+ + menadione
NAD+ + menadiol
show the reaction diagram
NADH + H+ + menaquinone
NAD+ + menaquinol
show the reaction diagram
-
the enzyme plays an essential role in maintaining a reduced ubiquinone-pool during infection (Mycobacterium tuberculosis is the causative agents of tuberculosis). The enzyme is not only essential to parasite survival in vivo but may also contribute to the severity and outcome of disease. Type II NADH:quinone oxidoreductase the membrane-bound respiratory enzyme differs from the canonical NADH:dehydrogenase (complex I), because it is not involved in the vectorial transfer of protons across membranes. Mycobacterium tuberculosis contains a branched respiratory chain terminating in a cytochrome bd (quinol) oxidase and an aa3-type cytochrome c oxidase. Both chains are fed by a menaquinol (MQH2) pool that is generated by four dehydrogenases; one succinate menaquinone oxidoreductase (SQR), one multimeric type I NADH: dehydrogenase (complex I), and two type II NADH: menaquinone oxidoreductases (ndh and ndhA). Transposon insertion knockout strategy reveals that disruption of the ndh gene is lethal
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?
NADH + H+ + menaquinone
NAD+ + menaquinone
show the reaction diagram
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?
NADH + H+ + nifuroxime
NAD+ + ?
show the reaction diagram
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-
-
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?
NADH + H+ + nitrobenzene
NAD+ + ?
show the reaction diagram
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-
-
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?
NADH + H+ + nitrofurantoin
NAD+ + ?
show the reaction diagram
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-
-
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?
NADH + H+ + oxidized dichlorophenolindophenol
NAD+ + reduced dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
NADH + H+ + tetramethyl-1,4-benzoquinone
NAD+ + tetramethyl-1,4-benzoquinol
show the reaction diagram
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-
-
-
?
NADH + H+ + ubiquinone
NAD+ + ubiquinol
show the reaction diagram
NADH + H+ + ubiquinone-0
NAD+ + ubiquinol-0
show the reaction diagram
NADH + H+ + ubiquinone-1
NAD+ + ubiquinol-1
show the reaction diagram
NADH + H+ + ubiquinone-10
NAD+ + ubiquinol-10
show the reaction diagram
NADH + H+ + ubiquinone-2
NAD+ + ubiquinol-2
show the reaction diagram
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-
-
-
?
NADH + H+ + vitamin K2
NAD+ + reduced vitamin K2
show the reaction diagram
NADH + H+ + vitamin K2
NAD+ + vitamin K2
show the reaction diagram
NADH + hexaamineruthenium(III) chloride
NAD+ + ?
show the reaction diagram
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-
-
-
?
NADH + hexaammineruthenium-(III)-chloride
NAD+ + ?
show the reaction diagram
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-
-
-
?
NADH + hexaammineruthenium-III-chloride
NAD+ + ?
show the reaction diagram
NADH + hexamineruthenium(III)-chloride
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + hexammineruthenium-(III)-chloride
NAD+ + ?
show the reaction diagram
NADH + menadione
NAD+ + menadiol
show the reaction diagram
NADH + menadione
NAD+ + reduced menadione
show the reaction diagram
-
-
-
-
?
NADH + menaquinone
NAD+ + menaquinol
show the reaction diagram
-
-
-
-
?
NADH + n-decylubiquinone + 5 H+[side1]
NAD+ + n-decylubiquinol + 4H+[side2]
show the reaction diagram
NADH + n-decylubiquinone + H+
NAD+ + n-decylubiquinol
show the reaction diagram
NADH + naphthoquinone
NAD+ + naphthoquinol
show the reaction diagram
-
-
-
-
?
NADH + nitroblue tetrazolium
NAD+ + reduced nitroblue tetrazolium
show the reaction diagram
-
-
-
-
?
NADH + O2
NAD+ + superoxide radical
show the reaction diagram
NADH + oxidized 2,6-dichlorophenolindophenol + H+
NAD+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
NADH + oxidized coenzyme Q1 + 5 H+[side1]
NAD+ + reduced coenzyme Q1 + 4 H+[side2]
show the reaction diagram
-
-
-
?
NADH + oxidized coenzyme Q1 + 5 H+[side1]
NAD+ + reduced coenzyme Q1 + 4H+[side2]
show the reaction diagram
-
-
-
?
NADH + phylloquinone
NAD+ + phylloquinol
show the reaction diagram
-
-
-
-
?
NADH + plastoquinone
NAD+ + plastoquinol
show the reaction diagram
NADH + ubiquinone
?
show the reaction diagram
NADH + ubiquinone
NAD+ + ubiquinol
show the reaction diagram
NADH + ubiquinone + 6 H+[side 1]
NAD+ + ubiquinol + 7 H+[side 2]
show the reaction diagram
NADH + ubiquinone + H+
NAD+ + ubiquinol
show the reaction diagram
-
-
-
-
?
NADH + ubiquinone-0
NAD+ + ubiquinol-0
show the reaction diagram
NADH + ubiquinone-1
NAD+ + reduced ubiquinone-1
show the reaction diagram
-
-
-
-
?
NADH + ubiquinone-1
NAD+ + ubiquinol-1
show the reaction diagram
NADH + ubiquinone-1 + 5 H+[side 1]
NAD+ + ubiquinol-1 + 4 H+[side 2]
show the reaction diagram
NADH + ubiquinone-1 + H+
NAD+ + ubiquinol
show the reaction diagram
-
-
-
-
?
NADH + ubiquinone-10
NAD+ + ubiquinol-10
show the reaction diagram
NADH + ubiquinone-10 + 5 H+[side 1]
NAD+ + ubiquinol-10 + 4 H+[side 2]
show the reaction diagram
-
-
-
-
?
NADH + ubiquinone-2
NAD+ + reduced ubiquinol-2
show the reaction diagram
NADH + ubiquinone-2
NAD+ + ubiquinol-2
show the reaction diagram
NADH + ubiquinone-6
NAD+ + ubiquinol-6
show the reaction diagram
NADH + ubiquinone-8
NAD+ + ubiquinol-8
show the reaction diagram
NADH + ubiquinone-9
NAD+ + ubiquinol-9
show the reaction diagram
-
-
-
-
-
NADPH + 2-methylnaphthoquinone
NADP+ + ?
show the reaction diagram
-
about 1% of the activity with NADH
-
-
?
NADPH + H+ + ubiquinone
NADP+ + ubiquinol
show the reaction diagram
NADPH + H+ + ubiquinone-1
NADP+ + ubiquinol-1
show the reaction diagram
-
at a slow rate
-
-
?
NADPH + ubiquinone + 6 H+[side 1]
NADP+ + ubiquinol + 7 H+[side 2]
show the reaction diagram
-
NADPH is a poor substrate of the complex
-
-
?
oxidized 2,6-dichlorophenolindophenol + NADH + H+
reduced 2,6-dichlorophenolindophenol + NAD+
show the reaction diagram
-
-
-
-
?
succinate + O2 + NAD+
NADH + ?
show the reaction diagram
-
-
-
-
?
ubiquinone + NADH + H+
ubiquinol + NAD+
show the reaction diagram
-
-
-
-
?
ubiquinone-1 + NADH + H+
ubiquinol-1 + NAD+
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
NADH + H+ + menaquinone
NAD+ + menaquinol
show the reaction diagram
-
the enzyme plays an essential role in maintaining a reduced ubiquinone-pool during infection (Mycobacterium tuberculosis is the causative agents of tuberculosis). The enzyme is not only essential to parasite survival in vivo but may also contribute to the severity and outcome of disease. Type II NADH:quinone oxidoreductase the membrane-bound respiratory enzyme differs from the canonical NADH:dehydrogenase (complex I), because it is not involved in the vectorial transfer of protons across membranes. Mycobacterium tuberculosis contains a branched respiratory chain terminating in a cytochrome bd (quinol) oxidase and an aa3-type cytochrome c oxidase. Both chains are fed by a menaquinol (MQH2) pool that is generated by four dehydrogenases; one succinate menaquinone oxidoreductase (SQR), one multimeric type I NADH: dehydrogenase (complex I), and two type II NADH: menaquinone oxidoreductases (ndh and ndhA). Transposon insertion knockout strategy reveals that disruption of the ndh gene is lethal
-
-
?
NADH + H+ + ubiquinone
NAD+ + ubiquinol
show the reaction diagram
NADH + H+ + ubiquinone-10
NAD+ + ubiquinol-10
show the reaction diagram
-
the natural substrate ubiquinone-10 is extremely hydrophobic
-
-
?
NADH + ubiquinone
?
show the reaction diagram
NADH + ubiquinone + 6 H+[side 1]
NAD+ + ubiquinol + 7 H+[side 2]
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
deamino-NADH
-
-
flavin
iron-sulfur centre
NADPH
riboflavin
complex contains one non-covalently bound FAD, one noncovalently bound riboflavin, ubiquinone-8 and a [2Fe–2S] cluster.. The phosphate group is attached at the 5'-position of the ribityl as in authentic FMN and the NADH:quinone oxidoreductase contains approximately 1.7 mol covalently bound FMN per mol non-covalently bound FAD. Each of the single NqrB and NqrC subunits in the NADH:quinone oxidoreductase carries a single FMN
ubiquinone
-
-
Ubiquinone-10
-
the enzyme contains 4.2-4.5 mol of ubiquinone-10 per 650000 Da enzyme
ubiquinone-8
complex contains one non-covalently bound FAD, one noncovalently bound riboflavin, ubiquinone-8 and a [2Fe–2S] cluster
[2Fe-2S]-center
complex contains one non-covalently bound FAD, one noncovalently bound riboflavin, ubiquinone-8 and a [2Fe–2S] cluster
additional information
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
-
dependent on
CaCl2
-
5-10 mM optimal for activity
NaCl
-
optimal concentration between 20 mM and 50 mM
[2Fe-2S]
-
four clusters in the NuoE subunit
[4Fe-4S] center
additional information
-
no FeS clusters are present in the protein
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxy-5-propyloctyl]octahydro-2,2'-bifuran-5-yl]-5-propylnonan-1-ol
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IC50: 870 nM
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyethyl]octahydro-2,2'-bifuran-5-yl]undecan-1-ol
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IC50: 280 nM
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyheptyl]octahydro-2,2'-bifuran-5-yl]pentadecan-1-ol
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IC50: 34 nM
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyheptyl]octahydro-2,2'-bifuran-5-yl]undecan-1-ol
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IC50: 3.2 nM
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxynonyl]octahydro-2,2'-bifuran-5-yl]tridecan-1-ol
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IC50: 7.5 nM
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxypropyl]octahydro-2,2'-bifuran-5-yl]undecan-1-ol
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IC50: 45 nM
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundec-3-yn-1-yl]octahydro-2,2'-bifuran-5-yl]dodec-4-yn-1-ol
-
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(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]dodecan-1-ol
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