Any feedback?
Literature summary for 1.6.5.2 extracted from
- Natural and synthetic quinones and their reduction by the quinone reductase enzyme NQO1: from synthetic organic chemistry to compounds with anticancer potential (2008), Org. Biomol. Chem., 6, 637-656.
Activating Compound
| Activating Compound | Comment | Organism | Structure |
|---|---|---|---|
| 1,2-dithiole-3-thione | induces enzyme expression | Homo sapiens |  |
| oltipraz | induces enzyme expression | Homo sapiens | |
| quercetin | induces enzyme expression | Homo sapiens | |
| sulforaphane | induces enzyme expression | Homo sapiens | |
| tert-butylhydroxy-anisole | induces enzyme expression | Homo sapiens | |
Application
| Application | Comment | Organism |
|---|---|---|
| medicine | individuals with the NQO1*2 allele are more susceptible to the toxic effects of benzene metabolites. Quinones that are good substrates for human NQO1 are more toxic to the NQO1 containing or expressing tumour cell lines than the NQO1-deficient cell lines. Quinones such as the biphenyl and naphthyl derivatives that are poor substrates show no selectivity or have no measurable cytotoxicity | Homo sapiens |
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
- |
Homo sapiens |
Crystallization (Commentary)
| Crystallization (Comment) | Organism |
|---|---|
- |
Mus musculus |
- |
Rattus norvegicus |
| dicumarol, RH1, E09 or ARH019 co-crystallized with NQO1 | Homo sapiens |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| dicumarol | most potent competitive inhibitor of QO1. Disadvantages with dicumarol in that it is not selective and can inhibit other enzymes in addition to NQO1 and it can also be extensively protein bound complicating its use in cellular assays | Homo sapiens | |
| ES936 | effective mechanism-based inhibitor. Inhibits NQO1 in a time- and concentration-dependent manner. In agreement with its role as mechanism-based (suicide substrate) inhibitor, requires the presence of cofactor NADH, and therefore a catalytic turnover, for effective enzyme inhibition. At 100 nanomol concentration, ES936 inhibits more than 95% of NQO1 activity in cells within 30 min, and since it is specific, appears to be a more useful biochemical tool than dicumarol for use in routine NQO1 assays | Homo sapiens | |
| ES936 | pancreatic tumour xenografts in mice grow significantly slower following treatment with ES936 | Mus musculus | |
Molecular Weight [Da]
| Molecular Weight [Da] | Molecular Weight Maximum [Da] | Comment | Organism |
|---|---|---|---|
| 60000 | - |
- |
Homo sapiens |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Homo sapiens | P15559 | - |
- |
| Mus musculus | - |
- |
- |
| Rattus norvegicus | - |
- |
- |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
- |
Rattus norvegicus |
- |
Homo sapiens |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| BxPC-3 cell | - |
Homo sapiens | - |
| MiaPaCa-2 cell | - |
Homo sapiens | - |
| pancreas | - |
Mus musculus | - |
| pancreatic cancer cell | upregulation or overexpression of the enzyme in tumours | Homo sapiens | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 2,3,5,6-tetramethyl-1,4-benzoquinone + NAD(P)H | - |
Homo sapiens | reduced 2,3,5,6-tetramethyl-1,4-benzoquinone + NAD(P)+ | - |
? | |
| 2,5-bis(aziridin-1-yl)-3,6-dimethylcyclohexa-2,5-diene-1,4-dione + NAD(P)H | excellent substrate | Homo sapiens | 2,5-bis(aziridin-1-yl)-3,6-dimethylbenzene-1,4-diol + NAD(P)+ | - |
? | |
| 2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylcyclohexane-1,4-dione + NAD(P)H | excellent substrate | Homo sapiens | 2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylbenzene-1,4-diol + NAD(P)+ | - |
? | |
| 2,5-dimethoxy-1,3-benzothiazole-4,7-dione + NAD(P)H | - |
Homo sapiens | 2,5-dimethoxy-1,3-benzothiazole-4,7-diol + NAD(P)+ | - |
? | |
| 2,5-dimethoxy-1-methyl-1H-benzimidazole-4,7-dione + NAD(P)H | - |
Homo sapiens | 2,5-dimethoxy-1-methyl-1H-benzimidazole-4,7-diol + NAD(P)+ | - |
? | |
| 3-(hydroxymethyl)-5-methoxy-1-methyl-2-phenyl-1H-indole-4,7-dione + NAD(P)H | excellent substrate | Homo sapiens | 3-(hydroxymethyl)-5-methoxy-1-methyl-2-phenyl-1H-indole-4,7-diol + NAD(P)+ | - |
? | |
| 5-aziridin-1-yl-3-(hydroxymethyl)-2-[(1E)-3-hydroxyprop-1-en-1-yl]-1-methyl-1H-indole-4,7-dione + NAD(P)H | - |
Homo sapiens | 5-aziridin-1-yl-3-(hydroxymethyl)-2-[(1E)-3-hydroxyprop-1-en-1-yl]-1-methyl-1H-indole-4,7-diol + NAD(P)+ | - |
? | |
| alpha-tocopherolquinone + NAD(P)H | - |
Rattus norvegicus | reduced alpha-tocopherolquinone + NAD(P)+ | - |
? | |
| alpha-tocopherolquinone + NAD(P)H | - |
Homo sapiens | reduced alpha-tocopherolquinone + NAD(P)+ | - |
? | |
| beta-lapachone + NAD(P)H | - |
Homo sapiens | reduced beta-lapachone + NAD(P)+ | - |
? | |
| diethyl [2,5-bis(aziridin-1-yl)-3,6-dioxocyclohexa-1,4-diene-1,4-diyl]biscarbamate + NAD(P)H | - |
Homo sapiens | diethyl [2,5-bis(aziridin-1-yl)-3,6-dihydroxybenzene-1,4-diyl]biscarbamate + NAD(P)+ | - |
? | |
| duroquinone + NAD(P)H | - |
Homo sapiens | reduced duroquinone + NAD(P)+ | - |
? | |
| geldanamycin + NAD(P)H | excellent substrate | Homo sapiens | reduced geldanamycin + NAD(P)+ | - |
? | |
| mitomycin C + NAD(P)H | poor substrate | Homo sapiens | reduced mitomycin C + NAD(P)+ | - |
? | |
| additional information | naphthoquinone-based vitamin (vitamin K1) is not a substrate for purified rat NQO1 | Rattus norvegicus | ? | - |
? | |
| streptonigrin + NAD(P)H | one of the best substrates for NQO1 | Homo sapiens | reduced streptonigrin + NAD(P)+ | - |
? | |
| ubiquinone + NAD(P)H | - |
Rattus norvegicus | reduced ubiquinone + NAD(P)+ | - |
? | |
| ubiquinone + NAD(P)H | - |
Homo sapiens | reduced ubiquinone + NAD(P)+ | - |
? | |
Subunits
| Subunits | Comment | Organism |
|---|---|---|
| homodimer | - |
Homo sapiens |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| DT-diaphorase | - |
Mus musculus |
| DT-diaphorase | - |
Rattus norvegicus |
| DT-diaphorase | - |
Homo sapiens |
| EC 1.6.99.2 | formerly | Mus musculus |
| EC 1.6.99.2 | formerly | Rattus norvegicus |
| EC 1.6.99.2 | formerly | Homo sapiens |
| NAD(P)H: quinone oxidoreductase 1 | - |
Mus musculus |
| NAD(P)H: quinone oxidoreductase 1 | - |
Rattus norvegicus |
| NAD(P)H: quinone oxidoreductase 1 | - |
Homo sapiens |
| NQO1 | - |
Mus musculus |
| NQO1 | - |
Rattus norvegicus |
| NQO1 | - |
Homo sapiens |
| QR1 | - |
Mus musculus |
| QR1 | - |
Rattus norvegicus |
| QR1 | - |
Homo sapiens |
| quinone reductase 1 | - |
Mus musculus |
| quinone reductase 1 | - |
Rattus norvegicus |
| quinone reductase 1 | - |
Homo sapiens |
Cofactor
| Cofactor | Comment | Organism | Structure |
|---|---|---|---|
| FAD | - |
Rattus norvegicus | |
| FAD | each subunit contains a non-covalently bound molecule of FAD | Homo sapiens | |
| NADH | C-terminal domain forms part of the binding site for the hydrophilic regions of NADH | Homo sapiens | |
| NADP+ | - |
Rattus norvegicus | |
| NADPH | C-terminal domain forms part of the binding site for the hydrophilic regions of NADPH | Homo sapiens | |
Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.
Release 2023.1 (January 2023)
Legal
Curated at
Member of
