Page last updated: 2024-11-09

4-aminostilbene

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

Description

4-aminostilbene: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1272788
CHEMBL ID69011
SCHEMBL ID219627
SCHEMBL ID219628
MeSH IDM0066088

Synonyms (58)

Synonym
bdbm50334280
4-stilbenamine
4-aminostilbene
benzenamine, 4-(2-phenylethenyl)-
nsc-36396
4-n-stilbenamine
p-styrylaniline
wln: zr d1u1r
nsc36396
834-24-2
OPREA1_401810
4-(2-phenylethenyl)benzenamine
nsc 36396
ccris 761
trans-4-aminostilbene
trans-4-n-stilbenamine
ccris 1872
(e)-4-(2-phenylethenyl)benzenamine
p-aminostilbene
trans-4-stilbene
brn 2208344
4-stilbenamine, (e)-
benzenamine, 4-(2-phenylethenyl)-, (e)-
STK065381
4-[(e)-2-phenylethenyl]aniline
HMS1542C08
A0854
AKOS000319518
BRD-K48379721-001-01-3
CHEMBL69011 ,
(e)-4-styrylaniline
BBL001781
4-styryl-phenylamine
4-[2-phenylethenyl]aniline
4309-66-4
4-12-00-03399 (beilstein handbook reference)
unii-di9wq08blu
di9wq08blu ,
F3145-0966
SCHEMBL219627
SCHEMBL219628
AB01322687-02
4-amino-trans-stilbene
4-[(e)-2-phenylethenyl]aniline #
stilbene, 4-amino- (e)-
trans-p-aminostilbene
4-[2-phenylethenyl]aniline, aldrichcpr
mfcd00025377
NCGC00328939-01
4-styrylaniline
VS-00875
4-[(1e)-2-phenylethenyl]aniline
aminostilbene, 4-
4-amino stilbene
D88339
Z57204889
DTXSID501032168
4-[(e)-2-phenyl-1-ethenyl]aniline

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Since the dose rate of aromatic amines, like AAF, in feeding studies for tumor formation is about 100 times below that examined in the isolated perfused livers, it is highly unlikely that oxidative stress is generated by metabolites able to undergo redox cycling and that reactive oxygen contributes to acute toxic effects."( Cytotoxicity of aromatic amines in rat liver and oxidative stress.
Hillesheim, W; Jaeschke, H; Neumann, HG, 1995
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AromataseHomo sapiens (human)IC50 (µMol)22.00000.00001.290410.0000AID1770524
Amine oxidase [flavin-containing] AHomo sapiens (human)IC50 (µMol)25.30000.00002.37899.7700AID551122
Amine oxidase [flavin-containing] AHomo sapiens (human)Ki6.67000.00192.379710.0000AID551122
Amine oxidase [flavin-containing] BHomo sapiens (human)IC50 (µMol)6.34000.00001.89149.5700AID551123
Amine oxidase [flavin-containing] BHomo sapiens (human)Ki2.73000.00061.777110.0000AID551123
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
negative regulation of chronic inflammatory responseAromataseHomo sapiens (human)
steroid biosynthetic processAromataseHomo sapiens (human)
estrogen biosynthetic processAromataseHomo sapiens (human)
androgen catabolic processAromataseHomo sapiens (human)
syncytium formationAromataseHomo sapiens (human)
negative regulation of macrophage chemotaxisAromataseHomo sapiens (human)
sterol metabolic processAromataseHomo sapiens (human)
female genitalia developmentAromataseHomo sapiens (human)
mammary gland developmentAromataseHomo sapiens (human)
uterus developmentAromataseHomo sapiens (human)
prostate gland growthAromataseHomo sapiens (human)
testosterone biosynthetic processAromataseHomo sapiens (human)
positive regulation of estradiol secretionAromataseHomo sapiens (human)
female gonad developmentAromataseHomo sapiens (human)
response to estradiolAromataseHomo sapiens (human)
biogenic amine metabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
positive regulation of signal transductionAmine oxidase [flavin-containing] AHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
response to xenobiotic stimulusAmine oxidase [flavin-containing] BHomo sapiens (human)
response to toxic substanceAmine oxidase [flavin-containing] BHomo sapiens (human)
response to aluminum ionAmine oxidase [flavin-containing] BHomo sapiens (human)
response to selenium ionAmine oxidase [flavin-containing] BHomo sapiens (human)
negative regulation of serotonin secretionAmine oxidase [flavin-containing] BHomo sapiens (human)
phenylethylamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
substantia nigra developmentAmine oxidase [flavin-containing] BHomo sapiens (human)
response to lipopolysaccharideAmine oxidase [flavin-containing] BHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to ethanolAmine oxidase [flavin-containing] BHomo sapiens (human)
positive regulation of dopamine metabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
hydrogen peroxide biosynthetic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to corticosteroneAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
iron ion bindingAromataseHomo sapiens (human)
steroid hydroxylase activityAromataseHomo sapiens (human)
electron transfer activityAromataseHomo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenAromataseHomo sapiens (human)
oxygen bindingAromataseHomo sapiens (human)
heme bindingAromataseHomo sapiens (human)
aromatase activityAromataseHomo sapiens (human)
protein bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
electron transfer activityAmine oxidase [flavin-containing] BHomo sapiens (human)
identical protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
endoplasmic reticulumAromataseHomo sapiens (human)
endoplasmic reticulum membraneAromataseHomo sapiens (human)
membraneAromataseHomo sapiens (human)
endoplasmic reticulumAromataseHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] AHomo sapiens (human)
cytosolAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial envelopeAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] BHomo sapiens (human)
dendriteAmine oxidase [flavin-containing] BHomo sapiens (human)
neuronal cell bodyAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID551123Inhibition of human recombinant MAOB expressed in insect cells by fluorescence assay2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Inhibition of monoamine oxidase by selected C5- and C6-substituted isatin analogues.
AID1261080Selectivity ratio of IC50 for HEK293 cells to IC50 for human HT-29 cells2015European journal of medicinal chemistry, Oct-20, Volume: 103Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes.
AID167927Carcinogenic activity on all sites after oral administration1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Computer-assisted structure-activity studies of chemical carcinogens. Aromatic amines.
AID1261077Cytotoxicity against human HT-29 cells assessed inhibition of cell proliferation after 2 days by MTT assay2015European journal of medicinal chemistry, Oct-20, Volume: 103Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes.
AID1261078Cytotoxicity against human MCF7 cells assessed inhibition of cell proliferation after 2 days by MTT assay2015European journal of medicinal chemistry, Oct-20, Volume: 103Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes.
AID167955Carcinogenic activity on ear duct after oral administration1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Computer-assisted structure-activity studies of chemical carcinogens. Aromatic amines.
AID168085Carcinogenic activity on liver after oral administration of the compound1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Computer-assisted structure-activity studies of chemical carcinogens. Aromatic amines.
AID167938Carcinogenic activity on breast after oral administration1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Computer-assisted structure-activity studies of chemical carcinogens. Aromatic amines.
AID1261082Inhibition of VEGF protein secretion in human HT-29 cells at 10 ug/mL after 72 hrs by ELISA relative to control2015European journal of medicinal chemistry, Oct-20, Volume: 103Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes.
AID388250Antiproliferative activity against human CNE1 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23
The design, synthesis, and anti-tumor mechanism study of N-phosphoryl amino acid modified resveratrol analogues.
AID1261079Cytotoxicity against HEK293 cells assessed inhibition of cell proliferation after 2 days by MTT assay2015European journal of medicinal chemistry, Oct-20, Volume: 103Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes.
AID1261089Down regulation of VEGF gene expression in human HT-29 cells at 10 ug/mL after 48 hrs by RT-qPCR analysis relative to control2015European journal of medicinal chemistry, Oct-20, Volume: 103Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes.
AID551122Inhibition of human recombinant MAOA expressed in insect cells by fluorescence assay2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Inhibition of monoamine oxidase by selected C5- and C6-substituted isatin analogues.
AID1770524Inhibition of human aromatase using dibenzylfluorescein as a substrate preincubated with NADPH regenerating system for 10 mins followed by substrate addition incubated for 30 mins by fluorescence based analysis2021European journal of medicinal chemistry, Nov-15, Volume: 224Synthesis, structure-activity relationships and molecular docking studies of phenyldiazenyl sulfonamides as aromatase inhibitors.
AID1261081Selectivity ratio of IC50 for HEK293 cells to IC50 for human MCF7 cells2015European journal of medicinal chemistry, Oct-20, Volume: 103Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes.
AID1261096Down regulation of hTERT gene expression in human HT-29 cells at 10 ug/mL after 48 hrs by RT-qPCR analysis relative to control2015European journal of medicinal chemistry, Oct-20, Volume: 103Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes.
AID168112Carcinogenic activity after oral administration1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Computer-assisted structure-activity studies of chemical carcinogens. Aromatic amines.
AID1261103Down regulation of c-Myc gene expression in human HT-29 cells at 10 ug/mL after 48 hrs by RT-qPCR analysis relative to control2015European journal of medicinal chemistry, Oct-20, Volume: 103Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes.
AID388251Antiproliferative activity against human CNE2 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23
The design, synthesis, and anti-tumor mechanism study of N-phosphoryl amino acid modified resveratrol analogues.
AID551124Selectivity ratio of Ki for human recombinant MAOA to Ki for human recombinant MAOB2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Inhibition of monoamine oxidase by selected C5- and C6-substituted isatin analogues.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (27.78)18.7374
1990's4 (22.22)18.2507
2000's2 (11.11)29.6817
2010's6 (33.33)24.3611
2020's1 (5.56)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.71

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 Index11.71 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.71)

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%
Other18 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]