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

New: Word Map on EC 1.6.5.3
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Search Reference ID:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


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
-
-
-
-
redox reaction
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
aerobic respiration I (cytochrome c)
-
-
aerobic respiration III (alternative oxidase pathway)
-
-
Fe(II) oxidation
-
-
Metabolic pathways
-
-
NAD/NADH phosphorylation and dephosphorylation
-
-
NADH to cytochrome bd oxidase electron transfer I
-
-
NADH to cytochrome bo oxidase electron transfer I
-
-
Oxidative phosphorylation
-
-
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
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Chlamydomonas sp.
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
var. melopepo, zucchini
-
-
Manually annotated by BRENDA team
strain ANN023
-
-
Manually annotated by BRENDA team
mutant derivative of strain BW25113 from which the nuo operon is deleted by genomic replacement
-
-
Manually annotated by BRENDA team
GR19N
-
-
Manually annotated by BRENDA team
strain GV102
-
-
Manually annotated by BRENDA team
strain MWC215
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Mus musculus C57/Bl
C57/Bl mice
-
-
Manually annotated by BRENDA team
Mycobacterium tuberculosis H37RV (ATCC 25618)
-
-
-
Manually annotated by BRENDA team
cultivar Samsun
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
subunit NqrB
UniProt
Manually annotated by BRENDA team
Vibrio cholerae ATCC 39541
subunit NqrB
UniProt
Manually annotated by BRENDA team
Vitis vinifera x Vitis riparia
-
-
-
Manually annotated by BRENDA team
Vitis vinifera x Vitis vinifera
-
-
-
Manually annotated by BRENDA team
-
-
-
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
-
-
?
benzoquinone + NADH + H+
benzohydroquinone + NAD+
show the reaction diagram
-
-
-
-
?
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
-
-
?
glutamate
?
show the reaction diagram
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
NADH + 3'-acetyl pyridine adenine dinucleotide
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + 6-decyl-ubiquinone
NAD+ + 6-decyl-ubiquinol
show the reaction diagram
-
-
-
-
?
NADH + anthraquinone-2,6-disulfonate
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + benzoquinone
NAD+ + benzoquinol
show the reaction diagram
-
-
-
-
?
NADH + benzoquinone + H+
NAD+ + benzoquinol
show the reaction diagram
-
-
-
-
?
NADH + caldariellaquinone
NAD+ + caldariellaquinol
show the reaction diagram
NADH + coenzyme Q0
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + coenzyme Q1
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + coenzyme Q1 + H+
NAD+ + reduced coenzyme Q1
show the reaction diagram
-
-
-
-
?
NADH + coenzyme Q10
?
show the reaction diagram
NADH + coenzyme Q2
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + decyl-ubiquinone
NAD+ + decyl-ubiquinol
show the reaction diagram
-
-
-
-
?
NADH + decyl-ubiquinone + H+
NAD+ + decyl-ubiquinol
show the reaction diagram
-
-
-
-
?
NADH + decylubiquinone
NAD+ + decylubiquinol
show the reaction diagram
NADH + decylubiquinone + H+
NAD+ + decylubiquinol
show the reaction diagram
-
-
-
-
?
NADH + duroquinone
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + duroquinone
NAD+ + duroquinol
show the reaction diagram
NADH + FAD
NAD+ + FADH2
show the reaction diagram
-
-
-
-
?
NADH + Fe(CN)63-
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 1,4-benzoquinone
NAD+ + 1,4-benzoquinol
show the reaction diagram
-
-
-
-
?
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
-
-
-
-
?
NADH + H+ + 2-methyl-1,4-benzoquinone
NAD+ + 2-methyl-1,4-benzoquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-methyl-1,4-naphthoquinone
NAD+ + 2-methyl-1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + 4-nitroacetophenone
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 4-nitrobenzaldehyde
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 4-nitrobenzoic acid
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 5,8-dioxo-1,4-naphthoquinone
NAD+ + 5,8-dioxo-1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
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
-
-
-
-
?
NADH + H+ + adriamycin
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + H+ + coenzyme Q1
NAD+ + reduced coenzyme Q1
show the reaction diagram
NADH + H+ + coenzyme Q2
NAD+ + reduced coenzyme Q2
show the reaction diagram
-
-
-
-
?
NADH + H+ + decylubiquinone
NAD+ + decylubiquinol
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
-
-
?
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
-
-
?
NADH + H+ + menaquinone
NAD+ + menaquinone
show the reaction diagram
-
-
-
-
?
NADH + H+ + nifuroxim
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + H+ + nitrobenzene
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + H+ + nitrofurantoin
NAD+ + ?
show the reaction diagram
-
-
-
-
?
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
-
-
-
-
?
NADH + H+ + ubiquinone
NAD+ + ubiquinol
show the reaction diagram
NADH + H+ + ubiquinone-0
NAD+ + ubiquinol-0
show the reaction diagram
NADH + H+ + ubiquinone-0
NAD+ + ubiquinol-1
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
-
-
-
-
?
NADH + hexaamineruthenium(III) chloride
NAD+ + ?
show the reaction diagram
-
-
-
-
?
NADH + hexaammineruthenium-(III)-chloride
NAD+ + ?
show the reaction diagram
-
-
-
-
?
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 + H+
NAD+ + n-decylubiquinol
show the reaction diagram
NADH + naphthoquinone
NAD+ + naphthoquinol
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 + 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 + H+
NAD+ + ubiquinol
show the reaction diagram
-
-
-
-
?
NADH + ubiquinone-10
NAD+ + ubiquinol-10
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
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
Mg2+
-
required 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
-
IC50: 870 nM
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyethyl]octahydro-2,2'-bifuran-5-yl]undecan-1-ol
-
IC50: 280 nM
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyheptyl]octahydro-2,2'-bifuran-5-yl]pentadecan-1-ol
-
IC50: 34 nM
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyheptyl]octahydro-2,2'-bifuran-5-yl]undecan-1-ol
-
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
-
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
-
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
-
-
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]dodecan-1-ol
-
-
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]undeca-3,5,7,9-tetrayn-1-ol
-
IC50: 0.000172 mM
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-5-ethyl-1-hydroxyoctyl]octahydro-2,2'-bifuran-5-yl]undecan-1-ol
-
IC50: 27 nM
(1R)-5-ethyl-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxy-5-propyloctyl]octahydro-2,2'-bifuran-5-yl]octan-1-ol
-
IC50: 1500 nM
(1R,1'R)-1,1'-((2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyl)-bis-(6-(4-n-butylphenoxy)hex-3-yn-1-ol)
-
-
(1R,1'R)-1,1'-((2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyl)-bis-(6-(4-n-butylphenoxy)hexan-1-ol)
-
-
(1R,1'R)-1,1'-(2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diylbis(5-[4-[(E)-(4-butylphenyl)diazenyl]phenoxy]pentan-1-ol)
-
48 nM, 70% inhibition
(1R,1'R)-1,1'-(2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diylbis(5-[4-[(Z)-(4-butylphenyl)diazenyl]phenoxy]pentan-1-ol)
-
48 nM, 70% inhibition
(1R,1'R)-1,1'-(2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diylbis[6-(2-butylphenoxy)hexan-1-ol]
-
IC50: 1000 nM
(1R,1'R)-1,1'-(2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diylbis[6-(4-butylphenoxy)hexan-1-ol]
-
IC50: 0.83 nM
(1R,1'R)-1,1'-(2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyldihexan-1-ol
-
IC50: 4500 nM
(1R,1'R)-1,1'-(2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyldioctan-1-ol
-
IC50: 45 nM
(1R,1'R)-1,1'-(2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyldiundecan-1-ol
(1R,1'S)-1,1'-(2R,5R)-tetrahydrofuran-2,5-diylditridecan-1-ol
(5S)-3-[(10R)-10-hydroxy-10-[(2R,2'R,5R,5'R)-5'-[(1R)-1 hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]decyl]-5-methylfuran-2(5H)-one
-
IC50: 0.0000012 mM
(5S)-3-[(13R)-13-hydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]tridec-8-yn-1-yl]-5-methylfuran-2(5H)-one
-
; IC50: 0.00000083 mM
(5S)-3-[(13R)-13-hydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]trideca-4,6,8,10-tetrayn-1-yl]-5-methylfuran-2(5H)-one
-
IC50: 0.0000017 mM
(5S)-3-[(13R)-13-hydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1S)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]tridec-10-yn-1-yl]-5-methylfuran-2(5H)-one
-
IC50: 0.000001 mM
(5S)-3-[(13R)-13-hydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1S)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]tridec-4-yn-1-yl]-5-methylfuran-2(5H)-one
-
IC50: 0.00000085 mM
(5S)-3-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(1S)-1-hydroxytridecyl]tetrahydrofuran-2-yl]trideca-4,6,8,10-tetrayn-1-yl]-5-methylfuran-2(5H)-one
-
IC50: 0.00028 mM
(5S)-3-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(1S)-1-hydroxytridecyl]tetrahydrofuran-2-yl]tridecyl]-5-methylfuran-2(5H)-one
-
IC50: 0.0000023 mM
(5S)-3-[(13S)-13-hydroxy-13-[(2R,5R)-5-[(1S)-1-hydroxytriecyl]tetrahydrofuran-2-yl]tridecyl]-5-methylfuran-2(5H)-one
-
IC50: 0.0000051 mM
(5S)-3-[(16R)-16-hydroxy-16-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]hexadecyl]-5-methylfuran-2(5H)-one
-
IC50: 0.000013 mM
(5S)-3-[(19R)-19-hydroxy-19-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]nonadecyl]-5-methylfuran-2(5H)-one
-
IC50: 0.000271 mM
(5S)-3-[(2E,13R)-13-hydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]tridec-2-en-4-yn-1-yl]-5-methylfuran-2(5H)-one
-
IC50: 0.0000011 mM
(5S)-3-[(5R)-5-hydroxy-5-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]pentyl]-5-methylfuran-2(5H)-one
-
IC50: 0.000014 mM
(5S)-3-[(7E,13S)-13-hydroxy-13-[(2R,5R)-5-[(1S)-1-hydroxytridecyl]tetrahydrofuran-2-yl]tridec-7-en-9-yn-1-yl]-5-methylfuran-2(5H)-one
-
IC50: 0.0000052 mM
(5S)-3-[(8E,13R)-13-hydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1S)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]tridec-8-en-10-yn-1-yl]-5-methylfuran-2(5H)-one
-
IC50: 0.00000092 mM
(5S)-3-[(8R)-8-hydroxy-8-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]octyl]-5-methylfuran-2(5H)-one
-
IC50: 0.0000016 mM
(5S)-3-[4-[(E)-(4-[[(4R)-4-hydroxy-4-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]tetrahydrofuran-2-yl]butyl]oxy]phenyl)diazenyl]benzyl]-5-methylfuran-2(5H)-one
-
-
(5S)-3-[4-[(E)-(4-[[(7R)-7-hydroxy-7-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]tetrahydrofuran-2-yl]heptyl]oxy]phenyl)diazenyl]benzyl]-5-methylfuran-2(5H)-one
-
-
(5S)-3-[4-[(Z)-(4-[[(4R)-4-hydroxy-4-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]tetrahydrofuran-2-yl]butyl]oxy]phenyl)diazenyl]benzyl]-5-methylfuran-2(5H)-one
-
-
(5S)-3-[4-[(Z)-(4-[[(7R)-7-hydroxy-7-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]tetrahydrofuran-2-yl]heptyl]oxy]phenyl)diazenyl]benzyl]-5-methylfuran-2(5H)-one
-
-
1-Geranyl-2-methylbenzimidazole
-
0.001 mM, 87% inhibition
1-hydroxy-2-octyl-4(1H)quinolone
-
-
1-methyl-4-phenylpyridinium
-
complex I inhibitor, which has no effect on mediobasal hypothalamic tuberoinfundibular dopamine neurons, but significantly increases the percentage of apoptag immunoreactive neurons in midbrain primary nigrostriatal dopamine and mesolimbic dopamine cultures
1-methyl-4-phenylpyridinium ion
-
inhibition of mitochondrial complex I. Neuroprotective effects of caffeine in the MPP+ model of apoptosis are mediated through activation of the ataxia telangiectasia mutated enzyme/p53 pathway. Caffeine decreases the expression of cyclin D and the transcription factor E2F-1, a regulator of apoptosis in neurons. Caffeine-mediated neuroprotection is not mediated through blockade of adenosine receptors because DPCPX and CGS-15943, two antagonists of these receptors, fail to attenuate apoptosis produced by 1-methyl-4-phenylpyridinium ion treatment
2',3'-dideoxycytidine
-
0.001 mM prevents the phosphorylation of the NDUFB11 subunit of complex I
2,3-dimethoxy-5-methyl-6-[(6-methylimidazo[2,1-b][1,3]thiazol-5-yl)methyl]benzo-1,4-quinone
-
0.00028 mM, NADH-coenzyme Q1 activity
2,6-dichlorophenolindophenol
-
-
2-(4-butylbenzylamino)-3-methylchromen-4-one
-
-
2-(4-butylbenzyloxy)-3-methylchromen-4-one
-
-
2-decyl-4-quinazolinyl amine
2-n-decyl-4-quinazolinylamine
-
0.001 mM, 73% inhibition
2-n-decyl-quinazoline-4-yl-amine
-
IC50: 0.0004 mM
2-[(2,6-dimethylimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-5,6-dimethoxy-3-methylbenzo-1,4-quinone
-
0.00077 mM, NADH-coenzyme Q1 activity
2-[(4-butylbenzyl)sulfanyl]-3-methyl-4H-chromen-4-one
-
-
2-[(6-chloro-2,3-dihydroimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-5,6-dimethoxy-3-methylbenzo-1,4-quinone
-
0.00065 mM, NADH-coenzyme Q1 activity
2-[(6-chloro-2-methylimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-5,6-dimethoxy-3-methylbenzo-1,4-quinone
-
0.00025 mM, NADH-coenzyme Q1 activity
2-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-5,6-dimethoxy-3-methylbenzo-1,4-quinone
-
0.00096 mM, NADH-coenzyme Q1 activity
2-[4-(4-fluorobutyl)benzylamino]-3-methylchromen-4-one
-
-
2-[4-(4-fluorobutyl)benzyloxy]-3-methylchromen-4-one
-
-
2-[4-(4-fluorobutyl)benzylsulfanyl]-3-methylchromen-4-one
-
most potent inhibitor. 30 min after high uptake of the radiotracer from the blood pool into the myocardium, kidney, and liver. After 2 h about 66% of the activity in the myocardium at 30 min has been retained, whereas ca. 70% has been cleared from the liver and kidney
3'-azido-3'-deoxythymidine
-
0.01 and 0.05 mM prevent the phosphorylation of the NDUFB11 subunit of complex I. This is associated with a decrease in complex I activity
3'-azido-3'-deoxythymidine monophosphate
-
0.15 mM prevents the phosphorylation of the NDUFB11 subunit of complex I. This is associated with a decrease in complex I activity
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3-azido-ubiquinone-2
37-methoxyquinoxalinone
-
IC50: 10 nM
39-pyridopyrazinone
-
IC50: 17 nM
4-(4-benzyl-phenoxy)-N-(3,4-dimethoxy-benzyl)-benzamide
-
-
4-(4-tert-butyl-phenoxy)-N-(3,4-dimethoxy-benzyl)-benzamide
5-(N-ethyl)-N-isopropylamiloride
-
IC50 : 0.1 mM
5-(N-ethyl-N-isopropyl)amiloride
-
-
5BM-GX
-
inhibits transhydrogenation reaction with NADH and 3'-acetyl pyridine adenine dinucleotide
6-amino-4-(4-tert-butylphenethylamino)quinazoline
6-azido-4-(4-iodophenethylamino)quinazoline
6-azido-N-[2-(4-tert-butylphenyl)ethyl]-6,7-dihydroquinazolin-4-amine
-
9-amino-6-chloro-2-methoxyacridine
-
0.0005 mM
ADP-ribose
AMP
-
dead-end inhibitor, linear competitive inhibitor of NADH, linear uncompetitive inhibitor of oxidized 2,6-dichlorophenol indophenol
AMS-GX
-
inhibits transhydrogenation reaction with NADH and 3'-acetyl pyridine adenine dinucleotide
Amytal
-
0.5 mM, 50% inhibition
antimycin A
-
0.0009 mM
arylazido-beta-alanyl-NAD+
-
competitive inhibition towards NADH and ferricyanide
atovaquone
-
20 nM, complete inhibition of partially purified enzyme. Inhibition of complex I represents a likely mechanism of the known antileishmanial activity of the drug
Ba2+
-
1 mM
Barbiturates
-
-
-
benzamil
benzimidazole
-
0.001 mM, 72% inhibition
benzo (1,2,3) thiadiazole-7-carbothioic acid S-methyl ester
-
0.075 mM, strong inhibition
benzoxazinone
-
0.001 mM, 76% inhibition
bis-tetrahydrofuran acetogenin
-
the additional methylenes enhance the hydrophobicity of the spacer region, which may be thermodynamically advantageous for bringing the polar gamma-lactone ring into the membrane-embedded segment of complex I
-
bullatacin
CaCl2
-
50 mM or greater
capsaicin
capsaicin-40
-
0.01 mM
carbonyl-cyanide-p-trifluoro-methoxy-phenylhydrazone
-
0.001 mM
carvedilol
-
decreases mitochondrial complex I activity, which is associated with an increase in mitochondrial H2O2 production, total glutathione and protein thiols content
Cd2+
-
1 mM, potent inhibitor
Co2+
-
1 mM
Cu2+
-
1 mM
Demerol
-
-
dicoumarol
-
-
dicyclohexylcarbodi-imide
-
90% inhibition, IC50: 0.25 mM
Dicyclohexylcarbodiimide
-
-
diphenyl iodonium
-
maximal inhibition after preincubation with NADH, more complete inhibition with the more hydrophobic electron acceptors such as ubiquinone-1 or ubiquinone-2 as electron acceptor compared to the more hydrophilic ones, such as ubiquinone-0 or dichloroindophenol
diphenyl iodonium chloride
-
0.001 mM and above
diphenyleineiodonium
-
does not inhibit superoxide generation
diphenylene iodinium chloride
-
-
diphenylene iodonium
-
75% inhibition, IC50: 0.013 mM
diphenylene iodonium chloride
-
0.001 mM and above
diphenyleneiodonium
-
strongly inhibits superoxide production by complex I driven by reverse electron transport from succinate. Inhibition of superoxide production is not dependent on changes in the pH gradient. The inhibitor does not react with the flavin of complex I
DL-homocysteic acid
-
marked (ca. 64%) decrease of respiratory chain complex I activity in the cerebral cortex of immature rats following seizures induced by bilateral intracerebroventricular infusion of DL-homocysteic acid (600 nanomol/side). Decrease is already evident during the acute phase of seizures (60-90 min after infusion) and persists for at least 20 h after the seizures. Inhibition is selective for complex I since activities of complex II and IV and citrate synthase remain unaffected. Inhibition of complex I activity is not associated with changes in complex I content. Enhanced production of reactive oxygen species by inhibited complex I in mitochondria from DL-homocysteic acid-treated animals. Competitive NMDA receptor antagonist AP7, a selective and potent group II mGluR agonist (2R,4R)-APDC and a highly selective group III mGluR, subtype 8, agonist (S)-3,4-DCPG, significantly reduce the extent of complex I inhibition. The superoxide dismutase mimetic Tempol and a selective peroxynitrite scavenger and decomposition catalyst FeTPPS provide a significant attenuation of complex I inhibition associated with DL-homocysteic acid-induced seizures
dodecyl-beta-D-maltoside
-
leads to immediate loss of activity
doxorubicin
-
; maximal inhibition at 0.001 mM
DTNB
-
-
fenazaquin
-
-
fenpyroximate
ferricyanide
-
inhibits the interaction of the oxidized enzyme with NADH
flavone
flutamide
-
inhibits complex I of the electron transport chain to a greater extent than a nitro to cyano analogue of flutamide. As compared to the nitro to cyano analogue of flutamide, the nitroaromatic group of flutamide enhances cytotoxicity to hepatocytes, likely through mechanisms involving mitochondrial dysfunction and ATP depletion that include complex I inhibition
imidazole
-
0.001 mM, 75% inhibition
liponox DCH
-
inhibitory at concentrations higher than 0.02%
-
Mersalyl
-
0.3 mM, 77% inhibition of NADH-ubiquinone-1 reductase activity, 96% inhibition of NADH-potassium ferricyanide reductase activity
metformin
-
inhibits complex I activity, associated with LPS-induced neutrophil activation. Metformin prevents LPS-induced acute lung injury
Mg2+
-
inhibition of the enzyme in its inactive form, in its active form the enzyme complex is not sensitive
Mn2+
-
1 mM
molvizarin
-
-
-
Myxothiazol
N,N'-dicyclohexylcarbodiimide
-
2 mM, 71% inhibition
N-(3,4-dimethoxy-benzyl)-4-[4-(1,1-dimethyl-propyl)-phenoxy]-benzamide
-
-
N-ethylmaleimide
nanaomycin A
-
-
NEM
-
inhibition of the enzyme in its inactive form, in its active form the enzyme complex is not sensitive
Ni2+
-
1 mM, potent inhibitor
nigericin
-
0.0125 mM
otivarin
-
-
oxygen
-
O2 induces self-inactivation of the enzyme via the formation of protein radicals
p-Chloromercuriphenyl sulfonic acid
-
0.1 mM, 50% inhibition
palmitate
-
IC50: 0.009 mM, at 25°C and pH 8.0
piercidin
-
-
piercidin A
piericidin
Piericidin A
Polymyxin B
-
in the presence of polymyxin B, enzyme kinetics changes from the Michaelis–Menten type to substrate inhibition kinetics with the substrate inhibition
pyridaben
pyridabene
quinoxalinone
-
0.001 mM, 79% inhibition
reduced 2,6-dichlorophenolindophenol
-
-
reduced coenzyme Q1
-
product inhibition
Rhein
-
i.e. 4,5-dioxy-anthraquinone-z-carbonic acid, competes for a NADH-binding site
rolliniastatin
rolliniastatin-1
-
-
rolliniastatin-2
rotenone
salicylic acid
-
0.5 mM, 45% inhibition
Sodium azide
-
10 mM
squamocin
squamocin M
-
IC50: 0.00000085 mM
squamocin-quinoxalinone
-
-
squamocin-triazine
-
-