Page last updated: 2024-11-06

2-acetylamino-3-chloro-1,4-naphthoquinone

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Description

2-acetylamino-3-chloro-1,4-naphthoquinone: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72754
CHEMBL ID153133
SCHEMBL ID6190569
MeSH IDM0558880

Synonyms (44)

Synonym
CBMICRO_020426
acetamide,4-dihydro-1,4-dioxo-2-naphthyl)-
acetamide,4-dihydro-1,4-dioxo-2-naphthalenyl)-
2-chloro-3-acetamidonaphthoquinone
5397-78-4
nsc4264
nsc-4264
n-(3-chloro-1,4-dioxo-1,4-dihydro-2-naphthalenyl)acetamide
AO-080/04036037
nsc 4264
acetamide, n-(1,4-dihydro-3-chloro-1,4-dioxo-2-naphthyl)-
brn 0524965
2-acetamido-3-chloro-1,4-naphthoquinone
acetamide, n-(3-chloro-1,4-dihydro-1,4-dioxo-2-naphthyl)-
acetamide, n-(3-chloro-1,4-dihydro-1,4-dioxo-2-naphthalenyl)-
n-(3-chloro-1,4-dihydro-1,4-dioxo-2-naphthyl)acetamide
BIM-0020413.P001
STK135423
n-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide
sj000067071
CHEMBL153133 ,
n-(3-chloro-1,4-dioxonaphthalen-2-yl)acetamide
AKOS001031800
CCG-5087
4-14-00-00411 (beilstein handbook reference)
AB00075390-01
2-acety-lamino-3-chloro-1,4-naphthoquinone
2-acetylamino-3-chloro1,4-naphthoquinone
OMXMYDUYAUOFRX-UHFFFAOYSA-N
n-(3-chloro-1,4-dihydro-1,4-dioxo-2-naphthalenyl)acetamide
2-acetylamino-3-chloro-1,4-naphthoquinone
2-acetylamino-3chloro-1,4-naphthoquinone
SCHEMBL6190569
pnu-37802
DTXSID20202266
SR-01000198690-1
sr-01000198690
bdbm50479476
Z56763523
np-313
np313
np 313
CS-0105990
HY-129496
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Heat shock protein HSP 90-alphaHomo sapiens (human)IC50 (µMol)6.60000.00040.695010.0000AID347502
Heat shock protein HSP 90-betaHomo sapiens (human)IC50 (µMol)6.60000.00100.683610.0000AID347502
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (53)

Processvia Protein(s)Taxonomy
telomere maintenance via telomeraseHeat shock protein HSP 90-alphaHomo sapiens (human)
neuron migrationHeat shock protein HSP 90-alphaHomo sapiens (human)
positive regulation of protein phosphorylationHeat shock protein HSP 90-alphaHomo sapiens (human)
activation of innate immune responseHeat shock protein HSP 90-alphaHomo sapiens (human)
positive regulation of defense response to virus by hostHeat shock protein HSP 90-alphaHomo sapiens (human)
skeletal muscle contractionHeat shock protein HSP 90-alphaHomo sapiens (human)
mitochondrial transportHeat shock protein HSP 90-alphaHomo sapiens (human)
response to unfolded proteinHeat shock protein HSP 90-alphaHomo sapiens (human)
response to heatHeat shock protein HSP 90-alphaHomo sapiens (human)
response to coldHeat shock protein HSP 90-alphaHomo sapiens (human)
response to xenobiotic stimulusHeat shock protein HSP 90-alphaHomo sapiens (human)
response to salt stressHeat shock protein HSP 90-alphaHomo sapiens (human)
positive regulation of lamellipodium assemblyHeat shock protein HSP 90-alphaHomo sapiens (human)
cardiac muscle cell apoptotic processHeat shock protein HSP 90-alphaHomo sapiens (human)
regulation of protein ubiquitinationHeat shock protein HSP 90-alphaHomo sapiens (human)
positive regulation of protein polymerizationHeat shock protein HSP 90-alphaHomo sapiens (human)
positive regulation of interferon-beta productionHeat shock protein HSP 90-alphaHomo sapiens (human)
regulation of protein localizationHeat shock protein HSP 90-alphaHomo sapiens (human)
protein refoldingHeat shock protein HSP 90-alphaHomo sapiens (human)
response to cocaineHeat shock protein HSP 90-alphaHomo sapiens (human)
positive regulation of protein import into nucleusHeat shock protein HSP 90-alphaHomo sapiens (human)
regulation of apoptotic processHeat shock protein HSP 90-alphaHomo sapiens (human)
regulation of protein-containing complex assemblyHeat shock protein HSP 90-alphaHomo sapiens (human)
protein unfoldingHeat shock protein HSP 90-alphaHomo sapiens (human)
response to estrogenHeat shock protein HSP 90-alphaHomo sapiens (human)
protein insertion into mitochondrial outer membraneHeat shock protein HSP 90-alphaHomo sapiens (human)
positive regulation of nitric oxide biosynthetic processHeat shock protein HSP 90-alphaHomo sapiens (human)
positive regulation of protein catabolic processHeat shock protein HSP 90-alphaHomo sapiens (human)
positive regulation of cell sizeHeat shock protein HSP 90-alphaHomo sapiens (human)
response to antibioticHeat shock protein HSP 90-alphaHomo sapiens (human)
protein stabilizationHeat shock protein HSP 90-alphaHomo sapiens (human)
chaperone-mediated protein complex assemblyHeat shock protein HSP 90-alphaHomo sapiens (human)
positive regulation of cardiac muscle contractionHeat shock protein HSP 90-alphaHomo sapiens (human)
chaperone-mediated autophagyHeat shock protein HSP 90-alphaHomo sapiens (human)
cellular response to virusHeat shock protein HSP 90-alphaHomo sapiens (human)
regulation of postsynaptic membrane neurotransmitter receptor levelsHeat shock protein HSP 90-alphaHomo sapiens (human)
positive regulation of tau-protein kinase activityHeat shock protein HSP 90-alphaHomo sapiens (human)
telomerase holoenzyme complex assemblyHeat shock protein HSP 90-alphaHomo sapiens (human)
cellular response to heatHeat shock protein HSP 90-alphaHomo sapiens (human)
protein foldingHeat shock protein HSP 90-alphaHomo sapiens (human)
telomere maintenance via telomeraseHeat shock protein HSP 90-betaHomo sapiens (human)
placenta developmentHeat shock protein HSP 90-betaHomo sapiens (human)
response to unfolded proteinHeat shock protein HSP 90-betaHomo sapiens (human)
virion attachment to host cellHeat shock protein HSP 90-betaHomo sapiens (human)
positive regulation of transforming growth factor beta receptor signaling pathwayHeat shock protein HSP 90-betaHomo sapiens (human)
regulation of protein ubiquitinationHeat shock protein HSP 90-betaHomo sapiens (human)
negative regulation of proteasomal ubiquitin-dependent protein catabolic processHeat shock protein HSP 90-betaHomo sapiens (human)
positive regulation of phosphoprotein phosphatase activityHeat shock protein HSP 90-betaHomo sapiens (human)
regulation of protein localizationHeat shock protein HSP 90-betaHomo sapiens (human)
negative regulation of apoptotic processHeat shock protein HSP 90-betaHomo sapiens (human)
positive regulation of nitric oxide biosynthetic processHeat shock protein HSP 90-betaHomo sapiens (human)
positive regulation of cell differentiationHeat shock protein HSP 90-betaHomo sapiens (human)
chaperone-mediated protein complex assemblyHeat shock protein HSP 90-betaHomo sapiens (human)
regulation of cell cycleHeat shock protein HSP 90-betaHomo sapiens (human)
chaperone-mediated protein foldingHeat shock protein HSP 90-betaHomo sapiens (human)
cellular response to interleukin-4Heat shock protein HSP 90-betaHomo sapiens (human)
supramolecular fiber organizationHeat shock protein HSP 90-betaHomo sapiens (human)
negative regulation of proteasomal protein catabolic processHeat shock protein HSP 90-betaHomo sapiens (human)
telomerase holoenzyme complex assemblyHeat shock protein HSP 90-betaHomo sapiens (human)
positive regulation of protein localization to cell surfaceHeat shock protein HSP 90-betaHomo sapiens (human)
cellular response to heatHeat shock protein HSP 90-betaHomo sapiens (human)
protein foldingHeat shock protein HSP 90-betaHomo sapiens (human)
protein stabilizationHeat shock protein HSP 90-betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (40)

Processvia Protein(s)Taxonomy
UTP bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
CTP bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
RNA bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
mRNA bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
protein bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
ATP bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
GTP bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
ATP hydrolysis activityHeat shock protein HSP 90-alphaHomo sapiens (human)
sulfonylurea receptor bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
protein phosphatase bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
MHC class II protein complex bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
nitric-oxide synthase regulator activityHeat shock protein HSP 90-alphaHomo sapiens (human)
TPR domain bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
ubiquitin protein ligase bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
dATP bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
identical protein bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
protein homodimerization activityHeat shock protein HSP 90-alphaHomo sapiens (human)
histone deacetylase bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
transmembrane transporter bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
tau protein bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
GTPase bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
Rho GDP-dissociation inhibitor bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
DNA polymerase bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
scaffold protein bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
disordered domain specific bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
ATP-dependent protein folding chaperoneHeat shock protein HSP 90-alphaHomo sapiens (human)
protein tyrosine kinase bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
unfolded protein bindingHeat shock protein HSP 90-alphaHomo sapiens (human)
RNA bindingHeat shock protein HSP 90-betaHomo sapiens (human)
double-stranded RNA bindingHeat shock protein HSP 90-betaHomo sapiens (human)
protein bindingHeat shock protein HSP 90-betaHomo sapiens (human)
ATP bindingHeat shock protein HSP 90-betaHomo sapiens (human)
ATP hydrolysis activityHeat shock protein HSP 90-betaHomo sapiens (human)
protein kinase regulator activityHeat shock protein HSP 90-betaHomo sapiens (human)
kinase bindingHeat shock protein HSP 90-betaHomo sapiens (human)
protein kinase bindingHeat shock protein HSP 90-betaHomo sapiens (human)
MHC class II protein complex bindingHeat shock protein HSP 90-betaHomo sapiens (human)
nitric-oxide synthase regulator activityHeat shock protein HSP 90-betaHomo sapiens (human)
TPR domain bindingHeat shock protein HSP 90-betaHomo sapiens (human)
heat shock protein bindingHeat shock protein HSP 90-betaHomo sapiens (human)
ubiquitin protein ligase bindingHeat shock protein HSP 90-betaHomo sapiens (human)
peptide bindingHeat shock protein HSP 90-betaHomo sapiens (human)
identical protein bindingHeat shock protein HSP 90-betaHomo sapiens (human)
protein homodimerization activityHeat shock protein HSP 90-betaHomo sapiens (human)
histone deacetylase bindingHeat shock protein HSP 90-betaHomo sapiens (human)
ATP-dependent protein bindingHeat shock protein HSP 90-betaHomo sapiens (human)
protein folding chaperoneHeat shock protein HSP 90-betaHomo sapiens (human)
cadherin bindingHeat shock protein HSP 90-betaHomo sapiens (human)
protein dimerization activityHeat shock protein HSP 90-betaHomo sapiens (human)
tau protein bindingHeat shock protein HSP 90-betaHomo sapiens (human)
DNA polymerase bindingHeat shock protein HSP 90-betaHomo sapiens (human)
disordered domain specific bindingHeat shock protein HSP 90-betaHomo sapiens (human)
ATP-dependent protein folding chaperoneHeat shock protein HSP 90-betaHomo sapiens (human)
receptor ligand inhibitor activityHeat shock protein HSP 90-betaHomo sapiens (human)
histone methyltransferase bindingHeat shock protein HSP 90-betaHomo sapiens (human)
unfolded protein bindingHeat shock protein HSP 90-betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (32)

Processvia Protein(s)Taxonomy
extracellular regionHeat shock protein HSP 90-alphaHomo sapiens (human)
nucleusHeat shock protein HSP 90-alphaHomo sapiens (human)
nucleoplasmHeat shock protein HSP 90-alphaHomo sapiens (human)
cytoplasmHeat shock protein HSP 90-alphaHomo sapiens (human)
mitochondrionHeat shock protein HSP 90-alphaHomo sapiens (human)
cytosolHeat shock protein HSP 90-alphaHomo sapiens (human)
plasma membraneHeat shock protein HSP 90-alphaHomo sapiens (human)
cell surfaceHeat shock protein HSP 90-alphaHomo sapiens (human)
membraneHeat shock protein HSP 90-alphaHomo sapiens (human)
basolateral plasma membraneHeat shock protein HSP 90-alphaHomo sapiens (human)
apical plasma membraneHeat shock protein HSP 90-alphaHomo sapiens (human)
brush border membraneHeat shock protein HSP 90-alphaHomo sapiens (human)
secretory granule lumenHeat shock protein HSP 90-alphaHomo sapiens (human)
melanosomeHeat shock protein HSP 90-alphaHomo sapiens (human)
neuronal cell bodyHeat shock protein HSP 90-alphaHomo sapiens (human)
lysosomal lumenHeat shock protein HSP 90-alphaHomo sapiens (human)
dendritic growth coneHeat shock protein HSP 90-alphaHomo sapiens (human)
axonal growth coneHeat shock protein HSP 90-alphaHomo sapiens (human)
perinuclear region of cytoplasmHeat shock protein HSP 90-alphaHomo sapiens (human)
collagen-containing extracellular matrixHeat shock protein HSP 90-alphaHomo sapiens (human)
extracellular exosomeHeat shock protein HSP 90-alphaHomo sapiens (human)
endocytic vesicle lumenHeat shock protein HSP 90-alphaHomo sapiens (human)
sperm mitochondrial sheathHeat shock protein HSP 90-alphaHomo sapiens (human)
sperm plasma membraneHeat shock protein HSP 90-alphaHomo sapiens (human)
ficolin-1-rich granule lumenHeat shock protein HSP 90-alphaHomo sapiens (human)
protein-containing complexHeat shock protein HSP 90-alphaHomo sapiens (human)
plasma membraneHeat shock protein HSP 90-alphaHomo sapiens (human)
neuronal cell bodyHeat shock protein HSP 90-alphaHomo sapiens (human)
perinuclear region of cytoplasmHeat shock protein HSP 90-alphaHomo sapiens (human)
myelin sheathHeat shock protein HSP 90-alphaHomo sapiens (human)
cytosolHeat shock protein HSP 90-alphaHomo sapiens (human)
nucleusHeat shock protein HSP 90-alphaHomo sapiens (human)
COP9 signalosomeHeat shock protein HSP 90-betaHomo sapiens (human)
protein folding chaperone complexHeat shock protein HSP 90-betaHomo sapiens (human)
extracellular regionHeat shock protein HSP 90-betaHomo sapiens (human)
nucleusHeat shock protein HSP 90-betaHomo sapiens (human)
nucleoplasmHeat shock protein HSP 90-betaHomo sapiens (human)
cytoplasmHeat shock protein HSP 90-betaHomo sapiens (human)
mitochondrionHeat shock protein HSP 90-betaHomo sapiens (human)
cytosolHeat shock protein HSP 90-betaHomo sapiens (human)
cell surfaceHeat shock protein HSP 90-betaHomo sapiens (human)
membraneHeat shock protein HSP 90-betaHomo sapiens (human)
secretory granule lumenHeat shock protein HSP 90-betaHomo sapiens (human)
melanosomeHeat shock protein HSP 90-betaHomo sapiens (human)
neuronal cell bodyHeat shock protein HSP 90-betaHomo sapiens (human)
dendritic growth coneHeat shock protein HSP 90-betaHomo sapiens (human)
axonal growth coneHeat shock protein HSP 90-betaHomo sapiens (human)
perinuclear region of cytoplasmHeat shock protein HSP 90-betaHomo sapiens (human)
extracellular exosomeHeat shock protein HSP 90-betaHomo sapiens (human)
dynein axonemal particleHeat shock protein HSP 90-betaHomo sapiens (human)
ficolin-1-rich granule lumenHeat shock protein HSP 90-betaHomo sapiens (human)
protein-containing complexHeat shock protein HSP 90-betaHomo sapiens (human)
aryl hydrocarbon receptor complexHeat shock protein HSP 90-betaHomo sapiens (human)
HSP90-CDC37 chaperone complexHeat shock protein HSP 90-betaHomo sapiens (human)
perinuclear region of cytoplasmHeat shock protein HSP 90-betaHomo sapiens (human)
plasma membraneHeat shock protein HSP 90-betaHomo sapiens (human)
cytosolHeat shock protein HSP 90-betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID23482Partition coefficient (logP)1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Substituted 1,4-naphthoquinones vs. the ascitic sarcoma 180 of mice.
AID347638Antiproliferative activity against ERalpha negative/Her2 over expressing human SKBR3 cells after 72 hrs by MTS/PMS assay2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Synthesis and evaluation of Hsp90 inhibitors that contain the 1,4-naphthoquinone scaffold.
AID39233Effective dose that would give a 25% increase in the survival time against the ascitic sarcoma 180 in mice1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Substituted 1,4-naphthoquinones vs. the ascitic sarcoma 180 of mice.
AID347501Inhibition of Hsp90-dependent renaturation of firefly luciferase in rabbit reticulocyte lysate at 25 ug/mL2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Synthesis and evaluation of Hsp90 inhibitors that contain the 1,4-naphthoquinone scaffold.
AID347502Inhibition of Hsp90 in human SKBR3 cells assessed as down-regulation of Her2 protein by ELISA2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Synthesis and evaluation of Hsp90 inhibitors that contain the 1,4-naphthoquinone scaffold.
AID117491Maximum survival by an optimum dose at 4 mg/kg in treated to that of untreated mice1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Substituted 1,4-naphthoquinones vs. the ascitic sarcoma 180 of mice.
AID449708ST_JUDE: Plasmodium falciparum K1 EC50 (uM) as measured by SYBR green dye2010Nature, May-20, Volume: 465, Issue:7296
Chemical genetics of Plasmodium falciparum.
AID21140Solubility in water was determined1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Substituted 1,4-naphthoquinones vs. the ascitic sarcoma 180 of mice.
AID117228Tested for acute toxicity which is the single dose given intraperitoneally that will kill one-half of the mice within 5 days1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Substituted 1,4-naphthoquinones vs. the ascitic sarcoma 180 of mice.
AID449707ST_JUDE: Plasmodium falciparum 3D7 EC50 (uM) as measured by SYBR green dye2010Nature, May-20, Volume: 465, Issue:7296
Chemical genetics of Plasmodium falciparum.
AID347503Antiproliferative activity against ERalpha positive human MCF7 cells after 72 hrs by MTS/PMS assay2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Synthesis and evaluation of Hsp90 inhibitors that contain the 1,4-naphthoquinone scaffold.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (20.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)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: 12.53

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 Index12.53 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.53)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]