Page last updated: 2024-12-05

5-nitroacenaphthene

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

5-Nitroacenaphthene is a yellow crystalline solid that is used as an intermediate in the synthesis of dyes and pigments. It is also used as a starting material for the synthesis of other organic compounds. 5-nitroacenaphthene is a potent mutagen and has been shown to cause cancer in laboratory animals. The compound is known to undergo photochemical reactions, transforming it into an even more reactive species. The nitro group makes the molecule more susceptible to oxidation, leading to the formation of reactive oxygen species. These species can cause damage to DNA, proteins, and other cellular components, contributing to the mutagenic and carcinogenic properties of 5-nitroacenaphthene. The compound's reactivity and potential toxicity have led to research efforts to understand its environmental fate and potential risks to human health. Studies on the synthesis of 5-nitroacenaphthene and its derivatives aim to develop more efficient and sustainable methods for producing these compounds while minimizing environmental impact. Research on the biological activity and toxicology of 5-nitroacenaphthene is crucial for assessing its potential hazards and informing safe handling practices.'
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Cross-References

ID SourceID
PubMed CID11769
CHEMBL ID423081
CHEBI ID82350
SCHEMBL ID267240
MeSH IDM0105097

Synonyms (57)

Synonym
AC-4959
acenaphthylene, 1,2-dihydro-5-nitro-
nsc22421
nsc-22421
5-nitro-1,2-dihydroacenaphthylene
NCGC00091685-01
einecs 210-025-0
5-nitronaphthalene
brn 1876864
hsdb 4092
nsc 1312
ccris 438
nsc 22421
1,2-dihydro-5-nitroacenaphthylene
acenaphthene, 5-nitro-
5-nitroacenapthene
602-87-9
1,2-dihydro-5-nitro-acenaphthylene
5-nan
nsc1312
nsc-1312
5-nitronaphthalene ethylene
acenaphthylene,2-dihydro-5-nitro-
nci-c01967
5-nitroacenaphthene
wln: l566 1a lt&&j hnw
5-nitroacenaphthene, 85%
NCGC00091685-02
chebi:82350 ,
5-nitro-acenaphthene
CHEMBL423081
N0105
AKOS000121350
A832670
C19269
dtxsid3020960 ,
cas-602-87-9
dtxcid10960
tox21_302877
NCGC00256570-01
f023f6c79x ,
unii-f023f6c79x
4-05-00-01840 (beilstein handbook reference)
5-nitroacenaphthene [hsdb]
5-nitroacenaphthene [iarc]
FT-0620701
SCHEMBL267240
5-nitro-1,2-dihydroacenaphthylene #
BBL034664
STL428868
mfcd00014277
J-517853
acenaphthylene, 1,2-dihydro-5-nitro-; acenaphthene, 5-nitro- (6ci,7ci,8ci); 1,2-dihydro-5-nitroacenaphthylene; 5-nitroacenaphthene; nsc 1312; nsc 22421
Q27155891
VS-12631
D87692
5-nitroacenaphthene (contains 3-nitroacenaphthene)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
nitronaphthaleneA nitroarene that is naphthalene substituted by at least one nitro group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (35)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency19.95260.025120.237639.8107AID886
Chain B, HADH2 proteinHomo sapiens (human)Potency19.95260.025120.237639.8107AID886
15-lipoxygenase, partialHomo sapiens (human)Potency19.95260.012610.691788.5700AID887
pregnane X receptorRattus norvegicus (Norway rat)Potency100.00000.025127.9203501.1870AID651751
GLI family zinc finger 3Homo sapiens (human)Potency21.68990.000714.592883.7951AID1259369; AID1259392
AR proteinHomo sapiens (human)Potency27.68410.000221.22318,912.5098AID1259243; AID1259247; AID588516; AID743035; AID743042; AID743063
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency3.16230.011212.4002100.0000AID1030
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency32.11460.001022.650876.6163AID1224838; AID1224839; AID1224893
progesterone receptorHomo sapiens (human)Potency24.33650.000417.946075.1148AID1346795
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency29.58430.001530.607315,848.9004AID1224848; AID1224849; AID1259403
pregnane X nuclear receptorHomo sapiens (human)Potency54.48270.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency23.18540.000229.305416,493.5996AID743069; AID743075; AID743078
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency31.62280.001024.504861.6448AID588535
peroxisome proliferator activated receptor gammaHomo sapiens (human)Potency50.11870.001019.414170.9645AID588537
aryl hydrocarbon receptorHomo sapiens (human)Potency64.86010.000723.06741,258.9301AID743085; AID743122
Histone H2A.xCricetulus griseus (Chinese hamster)Potency71.30090.039147.5451146.8240AID1224845
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency38.69370.000627.21521,122.0200AID651741; AID720636; AID743202
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency31.62280.031610.279239.8107AID884; AID885
lethal factor (plasmid)Bacillus anthracis str. A2012Potency15.84890.020010.786931.6228AID912
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID23442Partition coefficient (logP)1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity.
AID318681Anticarcinogenic activity in rat assessed as induction of tumors per day2008Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6
QSAR modeling of the rodent carcinogenicity of nitrocompounds.
AID433903Hepatotoxicity in mouse assessed as carcinogenic potency2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Development of QSAR models for predicting hepatocarcinogenic toxicity of chemicals.
AID200690Mutagenic activity in an Ames test on Salmonella Typhimurium TA98; Activity is log of revertants/nmol1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity.
[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-19902 (40.00)18.7374
1990's1 (20.00)18.2507
2000's2 (40.00)29.6817
2010's0 (0.00)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: 20.29

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.29 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.29)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]