Page last updated: 2024-12-06

3-phenoxybenzoic acid

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

Description

3-phenoxybenzoic acid is an organic compound with the formula C13H10O3. It is a white solid that is soluble in organic solvents. The compound can be synthesized by reacting phenol with 3-bromobenzoic acid in the presence of a base. 3-phenoxybenzoic acid has been studied for its potential biological activity. For example, it has been shown to exhibit anti-inflammatory and antioxidant properties. The compound has also been investigated for its potential use as a herbicide. 3-phenoxybenzoic acid is of interest to researchers due to its unique structure and potential biological activity. Further research is needed to fully understand its properties and potential applications.'

3-phenoxybenzoic acid: metabolite associated with exposure to pyrethroid insecticides [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3-phenoxybenzoic acid : A phenoxybenzoic acid in which the phenoxy group is meta to the carboxy group. It is a metabolite of pyrethroid insecticides. [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]

Cross-References

ID SourceID
PubMed CID19539
CHEMBL ID663
CHEBI ID72631
SCHEMBL ID128732
MeSH IDM0068543

Synonyms (67)

Synonym
EN300-16783
meta-phenoxybenzoic acid
3-phoc6h4co2h
3-phoc6h4cooh
diphenyl ether 3-carboxylic acid
m-carboxydiphenyl ether
ENAMINE_000396
inchi=1/c13h10o3/c14-13(15)10-5-4-8-12(9-10)16-11-6-2-1-3-7-11/h1-9h,(h,14,15
einecs 223-121-2
3-phenoxybenzoic acid
brn 2105574
m-phenoxybenzoic acid
benzoic acid, m-phenoxy-
benzoic acid, 3-phenoxy-
CBDIVE_003261
3739-38-6
3-pba
m-(phenyloxy)benzoic acid
3-phenoxybenzoic acid, 98%
OPREA1_360977
AC-10910
m-phenoxybenzoic acid for cis-isomer
chebi:72631 ,
CHEMBL663 ,
HMS1395B22
P1253
3-phenoxy-benzoic acid
bdbm50060998
AKOS001026974
NCGC00248105-01
VJJ ,
dtxcid9018321
cas-3739-38-6
tox21_300610
NCGC00254257-01
dtxsid1038321 ,
3-carboxydiphenyl ether
STL262700
S3597
69dc2655vh ,
unii-69dc2655vh
AE-641/02381052
BP-11457
FT-0616313
SCHEMBL128732
3-phenoxy benzoic acid
m-phenoxy benzoic acid
cambridge id 5155939
W-106541
TS-03060
phenoxybenzoic acid, 3-
mfcd00002498
3-phenoxybenzoic acid, pestanal(r), analytical standard
sr-01000197248
SR-01000197248-1
BBL104374
pyrethroid tp
3-pbac
F14689
Q26840945
AMY28526
CS-W014941
SY045836
1793055-05-6
HY-W014225
3-(phenoxy-13c6)benzoic acid
Z56777879

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Clinical examination and analysis of different biochemical parameters in blood and serum samples showed in spite of the minimal absorption of the insecticide, there was no immediate adverse effect."( Preliminary evaluation on safety aspects in mosquito net impregnation with lambdacyhalothrin.
Baskaran, S; Das, LK; Das, PK; Kalyanasundaram, M, 1992
)
0.28
"01-1000μM) did not show neurotoxicity, 2'-OH- and 4'-OH-deltamethrin (10-1000μM) were more toxic than deltamethrin (10-1000μM)."( Cytotoxicity induced by deltamethrin and its metabolites in SH-SY5Y cells can be differentially prevented by selected antioxidants.
Anadón, A; Ares, I; Castellano, V; Martínez, M; Martínez, MA; Martínez-Larrañaga, MR; Ramos, E; Romero, A, 2012
)
0.38
" We modified the widely used Quick Easy Cheap Effective Rugged Safe (QuEChERS) method to measure several current-use pyrethroids (cis/trans-permethrin, cypermethrin, deltamethrin, esfenvalerate, bifenthrin, cyfluthrin, and cyhalothrin) and their environmental degradation products (3-PBA, cis/trans-DCCA, 4-F-3-PBA, DBCA, and MPA) in selected fresh fruits and vegetables."( Measurement of pyrethroids and their environmental degradation products in fresh fruits and vegetables using a modification of the quick easy cheap effective rugged safe (QuEChERS) method.
Graham, SE; Li, W; Morgan, MK; Starr, JM, 2016
)
0.43
" Although CYP has been shown to pose toxic effects in some immune cells, as of now the immunotoxicity of CYP on immune progenitor cells has not been well studied."( β-Cypermethrin and its metabolite 3-phenoxybenzoic acid induce cytotoxicity and block granulocytic cell differentiation in HL-60 cells.
Fu, Z; He, B; Jin, Y; Kong, B; Wang, X; Wei, L; Xie, X, 2018
)
0.76

Pharmacokinetics

ExcerptReferenceRelevance
" We developed and evaluated a physiologically based pharmacokinetic (PBPK) model to assess the exposure of flight attendants to the pyrethroid insecticide permethrin attributable to aircraft disinsection."( Studying permethrin exposure in flight attendants using a physiologically based pharmacokinetic model.
Isukapalli, SS; Wei, B; Weisel, CP, 2013
)
0.39

Bioavailability

ExcerptReferenceRelevance
"In this study, the bioavailability and enantioselectivity differences between bifenthrin (BF, typeⅠpyrethroid) and lambad-cyhalothrin (LCT, type Ⅱ pyrethroid) in earthworm (Eisenia fetida) were investigated."( Bioaccumulation and enantioselectivity of type I and type II pyrethroid pesticides in earthworm.
Chang, J; Li, J; Wang, H; Wang, Y; Xu, P, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" Biotransformation of orally dosed compounds did not occur in the intestine, but were absorbed and metabolized by liver (deltamethrin) and kidney (3-PBacid)."( Comparative metabolism of deltamethrin and 3-phenoxybenzoic acid in chickens.
Akhtar, MH; Mahadevan, S; Paquet, A, 1994
)
0.55
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human xenobiotic metaboliteAny human metabolite produced by metabolism of a xenobiotic compound in humans.
marine xenobiotic metaboliteAny metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms.
[role 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]

Drug Classes (1)

ClassDescription
phenoxybenzoic acidAn aromatic ether that is diphenyl ether in which one of the hydrogens is replaced by a carboxy 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 (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
SMAD family member 2Homo sapiens (human)Potency38.89520.173734.304761.8120AID1346859
SMAD family member 3Homo sapiens (human)Potency38.89520.173734.304761.8120AID1346859
estrogen nuclear receptor alphaHomo sapiens (human)Potency34.66540.000229.305416,493.5996AID743075
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency23.16840.001024.504861.6448AID743227
vitamin D (1,25- dihydroxyvitamin D3) receptorHomo sapiens (human)Potency10.96220.023723.228263.5986AID743222
aryl hydrocarbon receptorHomo sapiens (human)Potency39.86870.000723.06741,258.9301AID743085; AID743122
[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)
Aldo-keto reductase family 1 member C3Homo sapiens (human)IC50 (µMol)0.68000.05002.207010.0000AID257049
[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)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
retinoid metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
G protein-coupled receptor signaling pathwayAldo-keto reductase family 1 member C3Homo sapiens (human)
response to nutrientAldo-keto reductase family 1 member C3Homo sapiens (human)
steroid metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of cell population proliferationAldo-keto reductase family 1 member C3Homo sapiens (human)
male gonad developmentAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to starvationAldo-keto reductase family 1 member C3Homo sapiens (human)
farnesol catabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
cyclooxygenase pathwayAldo-keto reductase family 1 member C3Homo sapiens (human)
keratinocyte differentiationAldo-keto reductase family 1 member C3Homo sapiens (human)
progesterone metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
retinol metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
retinal metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
macromolecule metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
regulation of retinoic acid receptor signaling pathwayAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionAldo-keto reductase family 1 member C3Homo sapiens (human)
testosterone biosynthetic processAldo-keto reductase family 1 member C3Homo sapiens (human)
renal absorptionAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to calcium ionAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to prostaglandin stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to corticosteroid stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to jasmonic acid stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to prostaglandin D stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
negative regulation of retinoic acid biosynthetic processAldo-keto reductase family 1 member C3Homo sapiens (human)
regulation of testosterone biosynthetic processAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of endothelial cell apoptotic processAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of reactive oxygen species metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
retinal dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
aldo-keto reductase (NADPH) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
estradiol 17-beta-dehydrogenase [NAD(P)] activityAldo-keto reductase family 1 member C3Homo sapiens (human)
all-trans-retinol dehydrogenase (NAD+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
oxidoreductase activity, acting on NAD(P)H, quinone or similar compound as acceptorAldo-keto reductase family 1 member C3Homo sapiens (human)
phenanthrene 9,10-monooxygenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
dihydrotestosterone 17-beta-dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin H2 endoperoxidase reductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin D2 11-ketoreductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
geranylgeranyl reductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
ketoreductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin-F synthase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
15-hydroxyprostaglandin-D dehydrogenase (NADP+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
androsterone dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
5alpha-androstane-3beta,17beta-diol dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
testosterone dehydrogenase (NAD+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
androstan-3-alpha,17-beta-diol dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
testosterone 17-beta-dehydrogenase (NADP+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
ketosteroid monooxygenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
Delta4-3-oxosteroid 5beta-reductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
bile acid bindingAldo-keto reductase family 1 member C3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleusAldo-keto reductase family 1 member C3Homo sapiens (human)
cytoplasmAldo-keto reductase family 1 member C3Homo sapiens (human)
cytosolAldo-keto reductase family 1 member C3Homo sapiens (human)
extracellular exosomeAldo-keto reductase family 1 member C3Homo sapiens (human)
cytosolAldo-keto reductase family 1 member C3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
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.
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).
AID84392Dissociation constant after binding to human papillomavirus E2 DNA-binding domain (DBD) by observing the changes in [15N]-HSQC spectra.1997Journal of medicinal chemistry, Sep-26, Volume: 40, Issue:20
NMR-based discovery of lead inhibitors that block DNA binding of the human papillomavirus E2 protein.
AID257049Inhibition of recombinant human AKR1C32005Bioorganic & medicinal chemistry letters, Dec-01, Volume: 15, Issue:23
Nonsteroidal anti-inflammatory drugs and their analogues as inhibitors of aldo-keto reductase AKR1C3: new lead compounds for the development of anticancer agents.
AID204263The concentration effective to cause 50% hemolysis with sensitized sheep erythrocytes in the absence of complement2003Bioorganic & medicinal chemistry letters, Apr-07, Volume: 13, Issue:7
Synthesis of low molecular weight compounds with complement inhibition activity.
AID204562The concentration required to inhibit complement mediated hemolysis of sensitized sheep RBC2003Bioorganic & medicinal chemistry letters, Apr-07, Volume: 13, Issue:7
Synthesis of low molecular weight compounds with complement inhibition activity.
AID1159537qHTS screening for TAG (triacylglycerol) accumulators in algae2017Plant physiology, Aug, Volume: 174, Issue:4
Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (201)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (2.49)18.7374
1990's15 (7.46)18.2507
2000's26 (12.94)29.6817
2010's104 (51.74)24.3611
2020's51 (25.37)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.44

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 Index28.44 (24.57)
Research Supply Index5.37 (2.92)
Research Growth Index5.32 (4.65)
Search Engine Demand Index33.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.44)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (1.43%)5.53%
Reviews5 (2.38%)6.00%
Case Studies0 (0.00%)4.05%
Observational1 (0.48%)0.25%
Other201 (95.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]