Page last updated: 2024-11-10

5-methoxy-1,2-dimethyl-3-((4-nitrophenoxy)methyl)indole-4,7-dione

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

5-methoxy-1,2-dimethyl-3-((4-nitrophenoxy)methyl)indole-4,7-dione: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID4470790
CHEMBL ID357217
SCHEMBL ID3991028
MeSH IDM0412210

Synonyms (24)

Synonym
es936
5-methoxy-1,2-dimethyl-3-((4-nitrophenoxy)methyl)indole-4,7-dione
DB02400
es-936
5-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione
CHEMBL357217 ,
SCHEMBL3991028
bdbm50316155
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
192820-78-3
es 936
1xi90i177m ,
1h-indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-((4-nitrophenoxy)methyl)-
unii-1xi90i177m
AKOS024457934
DTXSID20172879
es936, >=98% (hplc)
J-012477
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]-1h-indole-4,7-dione
Q27093401
1h-indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]-
es-936;es936
AS-77932
AKOS040745184

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Primary hepatocytes isolated from mice dosed with CFB are resistant to APAP toxicity."( Role of NAD(P)H:quinone oxidoreductase 1 in clofibrate-mediated hepatoprotection from acetaminophen.
Aleksunes, LM; Kardas, MJ; Klaassen, CD; Manautou, JE; Moffit, JS; Slitt, AL, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
NADHomo sapiens (human)Ki0.45000.45000.45000.4500AID1354482
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (37)

Processvia Protein(s)Taxonomy
protein polyubiquitinationNADHomo sapiens (human)
response to ischemiaNADHomo sapiens (human)
NADH oxidationNADHomo sapiens (human)
ubiquinone metabolic processNADHomo sapiens (human)
xenobiotic metabolic processNADHomo sapiens (human)
nitric oxide biosynthetic processNADHomo sapiens (human)
response to oxidative stressNADHomo sapiens (human)
synaptic transmission, cholinergicNADHomo sapiens (human)
response to nutrientNADHomo sapiens (human)
response to toxic substanceNADHomo sapiens (human)
response to hormoneNADHomo sapiens (human)
response to carbohydrateNADHomo sapiens (human)
response to amineNADHomo sapiens (human)
removal of superoxide radicalsNADHomo sapiens (human)
protein catabolic processNADHomo sapiens (human)
response to estradiolNADHomo sapiens (human)
response to lipopolysaccharideNADHomo sapiens (human)
response to testosteroneNADHomo sapiens (human)
cellular response to oxidative stressNADHomo sapiens (human)
negative regulation of protein catabolic processNADHomo sapiens (human)
vitamin E metabolic processNADHomo sapiens (human)
vitamin K metabolic processNADHomo sapiens (human)
negative regulation of apoptotic processNADHomo sapiens (human)
response to alkaloidNADHomo sapiens (human)
positive regulation of neuron apoptotic processNADHomo sapiens (human)
innate immune responseNADHomo sapiens (human)
cell redox homeostasisNADHomo sapiens (human)
response to ethanolNADHomo sapiens (human)
response to electrical stimulusNADHomo sapiens (human)
cellular response to hydrogen peroxideNADHomo sapiens (human)
NADPH oxidationNADHomo sapiens (human)
cellular response to metal ionNADHomo sapiens (human)
negative regulation of ferroptosisNADHomo sapiens (human)
response to tetrachloromethaneNADHomo sapiens (human)
response to L-glutamineNADHomo sapiens (human)
response to hydrogen sulfideNADHomo sapiens (human)
response to flavonoidNADHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
RNA bindingNADHomo sapiens (human)
cytochrome-b5 reductase activity, acting on NAD(P)HNADHomo sapiens (human)
superoxide dismutase activityNADHomo sapiens (human)
protein bindingNADHomo sapiens (human)
NADPH dehydrogenase (quinone) activityNADHomo sapiens (human)
identical protein bindingNADHomo sapiens (human)
NADH:ubiquinone reductase (non-electrogenic) activityNADHomo sapiens (human)
NAD(P)H dehydrogenase (quinone) activityNADHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
nucleusNADHomo sapiens (human)
cytoplasmNADHomo sapiens (human)
cytosolNADHomo sapiens (human)
dendriteNADHomo sapiens (human)
neuronal cell bodyNADHomo sapiens (human)
synapseNADHomo sapiens (human)
cytosolNADHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID78405Cytotoxicity was measured on non-small cell lung cancer(NSCLC) in H460 cell lines.1998Journal of medicinal chemistry, Nov-19, Volume: 41, Issue:24
Indolequinone antitumor agents: correlation between quinone structure, rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase, and in vitro cytotoxicity.
AID303039Inhibition of human recombinant NQO1 expressed in MIA PaCa2 cells at 10 to 100 nM after 1 hrs2007Journal of medicinal chemistry, Nov-15, Volume: 50, Issue:23
Synthesis and evaluation of 3-aryloxymethyl-1,2-dimethylindole-4,7-diones as mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1) activity.
AID1354482Inhibition of recombinant human NQO1 expressed in Escherichia coli using DCPIP as substrate assessed as rate of reduction of DCPIP in presence of NADH after 5 mins by spectrophotometric analysis2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
NAD(P)H:Quinone Oxidoreductase 1 (NQO1) as a Therapeutic and Diagnostic Target in Cancer.
AID303044Cytotoxicity against human MIA PaCa2 cells after 72 hrs by MTT assay2007Journal of medicinal chemistry, Nov-15, Volume: 50, Issue:23
Synthesis and evaluation of 3-aryloxymethyl-1,2-dimethylindole-4,7-diones as mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1) activity.
AID1354483Inactivation of recombinant human NQO1 expressed in Escherichia coli using DCPIP as substrate assessed as partition ratio up to 200 nM by spectrophotometric analysis2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
NAD(P)H:Quinone Oxidoreductase 1 (NQO1) as a Therapeutic and Diagnostic Target in Cancer.
AID303043Cytotoxicity against human MIA PaCa2 cells after 4 hrs by MTT assay2007Journal of medicinal chemistry, Nov-15, Volume: 50, Issue:23
Synthesis and evaluation of 3-aryloxymethyl-1,2-dimethylindole-4,7-diones as mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1) activity.
AID232958Ratio of IC50 for H460 cells and H596 cells.1998Journal of medicinal chemistry, Nov-19, Volume: 41, Issue:24
Indolequinone antitumor agents: correlation between quinone structure, rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase, and in vitro cytotoxicity.
AID78560Cytotoxicity was measured on non-small cell lung cancer(NSCLC) in H596 cell lines.1998Journal of medicinal chemistry, Nov-19, Volume: 41, Issue:24
Indolequinone antitumor agents: correlation between quinone structure, rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase, and in vitro cytotoxicity.
AID1354481Inactivation of recombinant human NQO1 expressed in Escherichia coli using DCPIP as substrate assessed as rate of reduction of DCPIP by spectrophotometric analysis2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
NAD(P)H:Quinone Oxidoreductase 1 (NQO1) as a Therapeutic and Diagnostic Target in Cancer.
AID163296NQO1 inactivation assay1998Journal of medicinal chemistry, Nov-19, Volume: 41, Issue:24
Indolequinone antitumor agents: correlation between quinone structure, rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase, and in vitro cytotoxicity.
AID163298Metabolism by recombinant human NQO1,using an HPLC system designed to quantify both NADH oxidation and quinone reduction; Not detected1998Journal of medicinal chemistry, Nov-19, Volume: 41, Issue:24
Indolequinone antitumor agents: correlation between quinone structure, rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase, and in vitro cytotoxicity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (6.25)18.2507
2000's8 (50.00)29.6817
2010's7 (43.75)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.55

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.55 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index5.38 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.55)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (6.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (93.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]