Page last updated: 2024-11-05

4-(4-dimethylaminophenylazo)benzoic acid

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

Description

4-(4-Dimethylaminophenylazo)benzoic acid, also known as Methyl Red, is a synthetic organic compound that is commonly used as an acid-base indicator in chemistry. It is a weak organic acid that changes color from red in acidic solutions to yellow in basic solutions. The compound is synthesized through a diazo coupling reaction between diazotized 4-dimethylaminoaniline and benzoic acid. Methyl Red is widely used in the laboratory for pH determination, as it provides a distinct color change within a narrow pH range. It is also used in other applications, such as in the textile industry as a dye and in the pharmaceutical industry as a component of certain medications. The compound has been studied extensively for its properties and potential applications, including its use as an indicator for acid-base reactions, its ability to absorb light in the visible spectrum, and its potential for use in various chemical and biological assays.'

4-(4-dimethylaminophenylazo)benzoic acid: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID22650
CHEMBL ID1573563
SCHEMBL ID93488
MeSH IDM0174408

Synonyms (59)

Synonym
6268-49-1
benzoic acid, p-[[p-(dimethylamino)phenyl]azo]-
4-dimethylamino-4'-carboxylazobenzene
n,n-dimethyl-p-aminobenzeneazobenzoic acid
nsc36265
nsc-36265
benzoic acid, 4-[[4-(dimethylamino)phenyl]azo]-
4-carboxy-4'-(dimethylamino)azobenzene
MLS001195042 ,
smr000554599
4-{(e)-[4-(dimethylamino)phenyl]diazenyl}benzoic acid
dabcyl
4-[(1e)-2-[4-(dimethylamino)phenyl]diazen-1-yl]benzoic acid
mfcd00058988
AKOS001482920
4-dimethylaminoazobenzene-4'-carboxylic acid
M0423
para methyl red
p-methyl red
NCGC00245824-01
HMS2885N11
nsc 36265
benzoic acid, 4-((4-(dimethylamino)phenyl)azo)-
benzoic acid, p-((p-(dimethylamino)phenyl)azo)-
4-(4-dimethylaminophenylazo)benzoic acid
SCHEMBL93488
4-(4'-dimethylaminophenylazo)benzoic acid
CHEMBL1573563
4-((4-(dimethylamino)phenyl)diazenyl)benzoic acid
dabcyl acid
cid_22650
bdbm64210
4-[4-(dimethylamino)phenyl]azobenzoic acid
4-[[4-(dimethylamino)phenyl]diazenyl]benzoic acid
4-([4-(dimethylamino)phenyl]diazenyl)benzoic acid #
4-(4'-dimethylaminophenylazo)-benzoic acid
114143-63-4
(e)-4-((4-(dimethylamino)phenyl)diazenyl)benzoic acid
SR-01000106674-1
sr-01000106674
4-dimethylaminoazobenzene-4-carboxylic acid
FT-0721844
4-(4-dimethylaminophenyl)diazenylbenzoic acid
HY-D1045
4-dimethylaminoazobenzene-4 inverted exclamation mark -carboxylic acid
SY059974
Q10389868
FS-6003
dabcyl; para-methyl red
AC7920
4-dimethylaminoazobenzene-4?-carboxylic acid
CS-0100485
para-methyl red
para-methyl reddabcyl
F12230
DTXSID50862438
4-{[4-(dimethylamino)phenyl]diazenyl}benzoic acid
PD158031
AKOS040744057
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (30)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency29.93490.003245.467312,589.2998AID2517
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency25.11890.140911.194039.8107AID2451
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency25.11890.631035.7641100.0000AID504339
LuciferasePhotinus pyralis (common eastern firefly)Potency0.23930.007215.758889.3584AID588342
glp-1 receptor, partialHomo sapiens (human)Potency2.51190.01846.806014.1254AID624417
WRNHomo sapiens (human)Potency50.11870.168331.2583100.0000AID651768
phosphopantetheinyl transferaseBacillus subtilisPotency79.43280.141337.9142100.0000AID1490
ATAD5 protein, partialHomo sapiens (human)Potency0.00520.004110.890331.5287AID504467
thioredoxin glutathione reductaseSchistosoma mansoniPotency39.81070.100022.9075100.0000AID485364
regulator of G-protein signaling 4Homo sapiens (human)Potency79.43280.531815.435837.6858AID504845
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency35.48130.707936.904389.1251AID504333
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency10.00000.035520.977089.1251AID504332
NPC intracellular cholesterol transporter 1 precursorHomo sapiens (human)Potency0.01260.01262.451825.0177AID485313
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency15.84890.354828.065989.1251AID504847
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency2.90930.00419.984825.9290AID504444
importin subunit beta-1 isoform 1Homo sapiens (human)Potency100.00005.804836.130665.1308AID540263
DNA polymerase betaHomo sapiens (human)Potency10.00000.022421.010289.1251AID485314
flap endonuclease 1Homo sapiens (human)Potency47.08350.133725.412989.1251AID588795; AID720498
ras-related protein Rab-9AHomo sapiens (human)Potency0.00020.00022.621531.4954AID485297
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency29.93490.168316.404067.0158AID720504
snurportin-1Homo sapiens (human)Potency100.00005.804836.130665.1308AID540263
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency84.92140.425612.059128.1838AID504891
DNA polymerase eta isoform 1Homo sapiens (human)Potency3.90210.100028.9256213.3130AID588591; AID720502
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency16.20630.050127.073689.1251AID588590; AID720496
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency0.95690.00798.23321,122.0200AID2546; AID2551
DNA polymerase kappa isoform 1Homo sapiens (human)Potency31.62280.031622.3146100.0000AID588579
muscleblind-like protein 1 isoform 1Homo sapiens (human)Potency12.58930.00419.962528.1838AID2675
Rap guanine nucleotide exchange factor 3Homo sapiens (human)Potency79.43286.309660.2008112.2020AID720709
ATP-dependent phosphofructokinaseTrypanosoma brucei brucei TREU927Potency37.93300.060110.745337.9330AID485367
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Hsf1 proteinMus musculus (house mouse)EC50 (µMol)1.68400.160024.4900236.5000AID2382
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (20)

Processvia Protein(s)Taxonomy
angiogenesisRap guanine nucleotide exchange factor 3Homo sapiens (human)
adaptive immune responseRap guanine nucleotide exchange factor 3Homo sapiens (human)
signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 3Homo sapiens (human)
associative learningRap guanine nucleotide exchange factor 3Homo sapiens (human)
Rap protein signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of actin cytoskeleton organizationRap guanine nucleotide exchange factor 3Homo sapiens (human)
negative regulation of syncytium formation by plasma membrane fusionRap guanine nucleotide exchange factor 3Homo sapiens (human)
intracellular signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of GTPase activityRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of angiogenesisRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of angiogenesisRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of protein export from nucleusRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of stress fiber assemblyRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of syncytium formation by plasma membrane fusionRap guanine nucleotide exchange factor 3Homo sapiens (human)
establishment of endothelial barrierRap guanine nucleotide exchange factor 3Homo sapiens (human)
cellular response to cAMPRap guanine nucleotide exchange factor 3Homo sapiens (human)
Ras protein signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of insulin secretionRap guanine nucleotide exchange factor 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
guanyl-nucleotide exchange factor activityRap guanine nucleotide exchange factor 3Homo sapiens (human)
protein bindingRap guanine nucleotide exchange factor 3Homo sapiens (human)
protein domain specific bindingRap guanine nucleotide exchange factor 3Homo sapiens (human)
cAMP bindingRap guanine nucleotide exchange factor 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
plasma membraneRap guanine nucleotide exchange factor 3Homo sapiens (human)
cortical actin cytoskeletonRap guanine nucleotide exchange factor 3Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 3Homo sapiens (human)
microvillusRap guanine nucleotide exchange factor 3Homo sapiens (human)
endomembrane systemRap guanine nucleotide exchange factor 3Homo sapiens (human)
membraneRap guanine nucleotide exchange factor 3Homo sapiens (human)
lamellipodiumRap guanine nucleotide exchange factor 3Homo sapiens (human)
filopodiumRap guanine nucleotide exchange factor 3Homo sapiens (human)
extracellular exosomeRap guanine nucleotide exchange factor 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (75)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's11 (14.67)18.2507
2000's15 (20.00)29.6817
2010's38 (50.67)24.3611
2020's11 (14.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.49

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 Index10.49 (24.57)
Research Supply Index4.33 (2.92)
Research Growth Index4.82 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.49)

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%
Other75 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]