Page last updated: 2024-11-04

3-nitrobenzeneboronic acid

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

Cross-References

ID SourceID
PubMed CID1677
CHEMBL ID20945
SCHEMBL ID127723
SCHEMBL ID14071499
MeSH IDM0068413

Synonyms (71)

Synonym
AC-5363
3-nitrobenzeneboronic acid
13331-27-6
boronic acid, (3-nitrophenyl)-
nsc-59739
3-nitrophenylboronic acid ,
benzeneboronic acid, m-nitro-
nsc59739
m-nitrophenylboronic acid
wln: wnr cbqq
m-nitrobenzeneboronic acid
nsc 59739
brn 2938638
ai3-60393
(3-nitrophenyl)boronic acid
nsc-401539
nsc401539
DB02797
3-nitrophenylboronic acid, >=97%
NCGC00092010-01
STK503722
m-nitophenyl boronic acid
3-nitrophenyl boronic acid
CHEMBL20945 ,
AKOS000265274
FT-0659121
N0563
bdbm50067887
3-nitro-phenyl-1-dihydroxyborane
A806593
(3-nitrophenyl)boronic acid;3-nitrophenylboronic acid
NCGC00092010-02
(3-nitrophenyl)-boronic acid
EN300-54327
boronic acid, b-(3-nitrophenyl)-
meta-nitrobenzeneboronic acid
unii-jlc765w4pn
jlc765w4pn ,
FT-0645343
FT-0602438
AS-2715
AM20060323
AB00854
SCHEMBL127723
3-nitropenyl boronic acid
m-nitrophenyl boronic acid
3-nitrobenzene-boronic acid
3-nitro-phenylboronic acid
dihydroxy(3-nitrophenyl)borane
ZNRGSYUVFVNSAW-UHFFFAOYSA-N
3-nitrobenzene boronic acid
3-nitro phenyl boronic acid
3-nitrophenyl-boronic acid
meta-nitrophenylboronic acid
3-nitro benzene boronic acid
3-nitro-phenyl boronic acid
SCHEMBL14071499
DTXSID2065416
mfcd00007193
SY015120
J-512975
CS-W007413
F0001-0442
BBL104406
BCP18407
Q27093741
3-nitro phenylboric acid
PD007633
Z808609458
HY-W007413
3(nitrophenyl)boronic acid
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (10)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency8.91250.000811.382244.6684AID686978
67.9K proteinVaccinia virusPotency2.51190.00018.4406100.0000AID720579
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chymotrypsinogen ABos taurus (cattle)IC50 (µMol)200.00000.98004.05607.2000AID36989
Beta-lactamaseEscherichia coli K-12IC50 (µMol)5.00000.01502.46578.0000AID38396
Beta-lactamaseEscherichia coli K-12Ki1.70000.02703.64137.3000AID38397; AID38398
Trypsin-2Homo sapiens (human)IC50 (µMol)200.00000.00351.58464.4000AID44381
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)IC50 (µMol)200.00000.00031.38338.4000AID36989
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)IC50 (µMol)200.00000.00051.48357.8000AID36989
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)IC50 (µMol)200.00000.00311.73607.8000AID36989
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)IC50 (µMol)200.00000.00501.79627.8000AID36989
Angiotensin-converting enzymeRattus norvegicus (Norway rat)Ki1.70000.00011.96427.3000AID38398
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
digestionChymotrypsinogen ABos taurus (cattle)
antibiotic catabolic processBeta-lactamaseEscherichia coli K-12
response to antibioticBeta-lactamaseEscherichia coli K-12
proteolysisTrypsin-2Homo sapiens (human)
digestionTrypsin-2Homo sapiens (human)
antimicrobial humoral responseTrypsin-2Homo sapiens (human)
extracellular matrix disassemblyTrypsin-2Homo sapiens (human)
positive regulation of cell growthTrypsin-2Homo sapiens (human)
collagen catabolic processTrypsin-2Homo sapiens (human)
positive regulation of cell adhesionTrypsin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingChymotrypsinogen ABos taurus (cattle)
serpin family protein bindingChymotrypsinogen ABos taurus (cattle)
beta-lactamase activityBeta-lactamaseEscherichia coli K-12
hydrolase activityBeta-lactamaseEscherichia coli K-12
metalloendopeptidase activityTrypsin-2Homo sapiens (human)
serine-type endopeptidase activityTrypsin-2Homo sapiens (human)
calcium ion bindingTrypsin-2Homo sapiens (human)
protein bindingTrypsin-2Homo sapiens (human)
serine-type peptidase activityTrypsin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
extracellular regionChymotrypsinogen ABos taurus (cattle)
serine protease inhibitor complexChymotrypsinogen ABos taurus (cattle)
outer membrane-bounded periplasmic spaceBeta-lactamaseEscherichia coli K-12
periplasmic spaceBeta-lactamaseEscherichia coli K-12
extracellular regionTrypsin-2Homo sapiens (human)
extracellular spaceTrypsin-2Homo sapiens (human)
extracellular matrixTrypsin-2Homo sapiens (human)
azurophil granule lumenTrypsin-2Homo sapiens (human)
extracellular spaceTrypsin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID1862382Synergistic antibacterial activity against KPC-2 producing Escherichia coli BL21 (DE3) assessed as cefotaxime MIC at 5 ug/ml incubated for 16 to 20 hrs by microdilution method (Rvb = 16 ug/ml)2022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID67675Compound was tested for its specificity against Elastase1998Journal of medicinal chemistry, Nov-05, Volume: 41, Issue:23
Structure-based enhancement of boronic acid-based inhibitors of AmpC beta-lactamase.
AID1862380Synergistic antibacterial activity against KPC-2 producing Escherichia coli BL21 (DE3) assessed as cefotaxime MIC at 50 ug/ml incubated for 16 to 20 hrs by microdilution method (Rvb = 16 ug/ml)2022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID1862376Inhibition of bacterial beta-lactamase KPC-2 expressed in Escherichia coli BL21 (DE3) using nitrocefin as substrate assessed as inhibition constant by Cheng-Prusoff equation analysis2022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID1862393Cytotoxicity against HEK293 cells assessed as cell viability at 5 to 50 ug/ml incubated for 24 hrs in presence of cefotaxime by MTT assay relative to control2022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID1862377Acid dissociation constant, pKa of the compound in 0.1 M phosphate buffer at 0.1 mM at pH 4.3 to 10.9 by UV-visible spectrophotometric analysis2022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID38397Binding affinity towards AmpC beta-lactamase binding site from Escherichia coli2002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
Structure-based approach for binding site identification on AmpC beta-lactamase.
AID1862386Antibacterial activity against Escherichia coli assessed as bacterial growth inhibition at 5 to 50 ug/ml incubated for 16 to 20 hrs by microdilution method2022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID1862381Synergistic antibacterial activity against KPC-2 producing Escherichia coli BL21 (DE3) assessed as meropenem MIC at 50 ug/ml incubated for 16 to 20 hrs by microdilution method (Rvb = >= 64 ug/ml)2022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID1862379Antibacterial activity against Escherichia coli NCTC104182022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID482996Inhibition of AmpC beta lactamase by spectrophotometry2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Structural study of phenyl boronic acid derivatives as AmpC beta-lactamase inhibitors.
AID227937Binding constant with catechol dye alizarin red S in 0.1 M PBS buffer at the pH=7.52004Bioorganic & medicinal chemistry letters, Jan-05, Volume: 14, Issue:1
3-Methoxycarbonyl-5-nitrophenyl boronic acid: high affinity diol recognition at neutral pH.
AID1497005Inhibition of bacterial beta-lactamase KPC2 expressed in Escherichia coli BL21(DE3) assessed as potentiation of cefotaxime--induced inhibition of bacterial growth 50 ug/disc after overnight incubation by disk diffusion method2018Bioorganic & medicinal chemistry, 07-15, Volume: 26, Issue:11
Boronic acid inhibitors of the class A β-lactamase KPC-2.
AID437825Inhibition of penicillin-sensitive Streptococcus pneumoniae R6 PBP2X assessed as residual activity at 1000 uM preincubated for 60 mins before addition of substrate mixture of (R)-[2-(benzoylamino)propionylsulfanyl]acetic acid and 5,5'-dithiobis(2-nitroben2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of 3-(dihydroxyboryl)benzoic acids as D,D-carboxypeptidase R39 inhibitors.
AID1497004Inhibition of bacterial beta-lactamase KPC-22018Bioorganic & medicinal chemistry, 07-15, Volume: 26, Issue:11
Boronic acid inhibitors of the class A β-lactamase KPC-2.
AID1862383Synergistic antibacterial activity against KPC-2 producing Escherichia coli BL21 (DE3) assessed as meropenem MIC at 5 ug/ml incubated for 16 to 20 hrs by microdilution method (Rvb = >= 64 ug/ml)2022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID437817Inhibition of Actinomadura sp. R39 penicillin-binding protein assessed as residual activity at 1000 uM preincubated for 60 mins before addition of substrate mixture of (R)-[2-(benzoylamino)propionylsulfanyl]acetic acid and 5,5'-dithiobis(2-nitrobenzoic ac2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of 3-(dihydroxyboryl)benzoic acids as D,D-carboxypeptidase R39 inhibitors.
AID1497003Inhibition of bacterial AmpC2018Bioorganic & medicinal chemistry, 07-15, Volume: 26, Issue:11
Boronic acid inhibitors of the class A β-lactamase KPC-2.
AID1497000Inhibition of beta-lactamase CMY-4 in Escherichia coli G69 assessed as cefotaxime MIC at 50 ug/ml incubated for 16 hrs by broth microdilution method (Rvb >32 ug/ml)2018Bioorganic & medicinal chemistry, 07-15, Volume: 26, Issue:11
Boronic acid inhibitors of the class A β-lactamase KPC-2.
AID38396Compound was tested for its specificity against AmpC beta-lactamase1998Journal of medicinal chemistry, Nov-05, Volume: 41, Issue:23
Structure-based enhancement of boronic acid-based inhibitors of AmpC beta-lactamase.
AID38398Inhibitory activity against Escherichia coli AmpC beta-lactamase.1998Journal of medicinal chemistry, Nov-05, Volume: 41, Issue:23
Structure-based enhancement of boronic acid-based inhibitors of AmpC beta-lactamase.
AID1862384Dissociation constant, pKa of the compound in 0.1 M phosphate buffer by UV-visible spectrophotometer2022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID1496997Effect on growth of Escherichia coli BL21(DE3) at 50 ug/disk after overnight incubation by disk diffusion method2018Bioorganic & medicinal chemistry, 07-15, Volume: 26, Issue:11
Boronic acid inhibitors of the class A β-lactamase KPC-2.
AID1497001Inhibition of NDM-1 in Klebsiella pneumoniae NCTC 13443 assessed as cefotaxime MIC at 50 ug/ml incubated for 16 hrs by broth microdilution method (Rvb >32 ug/ml)2018Bioorganic & medicinal chemistry, 07-15, Volume: 26, Issue:11
Boronic acid inhibitors of the class A β-lactamase KPC-2.
AID1862374Potentiation of cefotaxime induced antibacterial activity against Escherichia coli BL21 (DE3) expressing pET30a KPC-2C plasmid assessed as increase in clearance zone of inhibition incubated for 16 to 18 hrs by CLSI based disc diffusion assay (Rvb = 18.5 +2022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID437828Inhibition of penicillin-resistant Streptococcus pneumoniae 5204 PBP2X assessed as residual activity at 1000 uM preincubated for 4 hrs before addition of substrate mixture of (R)-[2-(benzoylamino)propionylsulfanyl]acetic acid and 5,5'-dithiobis(2-nitroben2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of 3-(dihydroxyboryl)benzoic acids as D,D-carboxypeptidase R39 inhibitors.
AID1496999Inhibition of bacterial beta-lactamase KPC2 expressed in Escherichia coli BL21(DE3) assessed as cefotaxime MIC at 50 ug/ml incubated for 16 hrs by broth microdilution method (Rvb = 16 ug/ml)2018Bioorganic & medicinal chemistry, 07-15, Volume: 26, Issue:11
Boronic acid inhibitors of the class A β-lactamase KPC-2.
AID44381Compound was tested for its specificity against beta-trypsin1998Journal of medicinal chemistry, Nov-05, Volume: 41, Issue:23
Structure-based enhancement of boronic acid-based inhibitors of AmpC beta-lactamase.
AID1496998Potentiation of cefotaxime-induced antibacterial activity against Escherichia coli NCTC 10118 assessed as cefotaxime MIC after 16 hrs by broth microdilution technique (Rvb <=0.03 ug/ml)2018Bioorganic & medicinal chemistry, 07-15, Volume: 26, Issue:11
Boronic acid inhibitors of the class A β-lactamase KPC-2.
AID1862392Cytotoxicity against HEK293 cells assessed as cell viability at 5 to 50 ug/ml incubated for 24 hrs by MTT assay relative to control2022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID1497006Inhibition of bacterial beta-lactamase KPC2 expressed in Escherichia coli BL21(DE3) assessed as reduction in cefotaxime MIC at 50 ug/ml incubated for 16 hrs by broth microdilution method relative to untreated control2018Bioorganic & medicinal chemistry, 07-15, Volume: 26, Issue:11
Boronic acid inhibitors of the class A β-lactamase KPC-2.
AID1497002Inhibition of Beta-lactamase CTX-M in Klebsiella pneumoniae isolate 342 assessed as cefotaxime MIC at 50 ug/ml incubated for 16 hrs by broth microdilution method (Rvb >32 ug/ml)2018Bioorganic & medicinal chemistry, 07-15, Volume: 26, Issue:11
Boronic acid inhibitors of the class A β-lactamase KPC-2.
AID1862385Antibacterial activity against Staphylococcus aureus assessed as bacterial growth inhibition at 5 to 50 ug/ml incubated for 16 to 20 hrs by microdilution method2022European journal of medicinal chemistry, Oct-05, Volume: 240Triazole-substituted phenylboronic acids as tunable lead inhibitors of KPC-2 antibiotic resistance.
AID36989Compound was tested for its specificity against alpha-chymotrypsin1998Journal of medicinal chemistry, Nov-05, Volume: 41, Issue:23
Structure-based enhancement of boronic acid-based inhibitors of AmpC beta-lactamase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (11.54)18.7374
1990's3 (11.54)18.2507
2000's9 (34.62)29.6817
2010's9 (34.62)24.3611
2020's2 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.58

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 Index11.58 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index4.91 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.58)

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%
Other27 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]