Page last updated: 2024-11-05

phenylphosphonic acid

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

Description

Phenylphosphonic acid is a white crystalline solid with the formula C6H5PO(OH)2. It is a versatile reagent in organic synthesis, serving as a building block for various phosphorus-containing compounds. It is synthesized via the reaction of benzene with phosphorus trichloride followed by hydrolysis. Phenylphosphonic acid has a range of applications, including the production of flame retardants, pesticides, and pharmaceuticals. It is also used as a catalyst in organic reactions and as a precursor for the synthesis of other organophosphorus compounds. The compound exhibits diverse biological activities, including antimicrobial and antitumor properties. Research into phenylphosphonic acid and its derivatives focuses on exploring their potential as novel therapeutic agents, catalysts, and materials.'

phenylphosphonic acid: RN given refers to parent cpd; NM same as N1 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID15295
CHEMBL ID179801
CHEBI ID191118
SCHEMBL ID34998
MeSH IDM0081024

Synonyms (43)

Synonym
ai3-52844
brn 2245168
einecs 216-388-1
nsc 145
wln: qpqo&r
phosphonic acid, phenyl-
nsc-145
nsc145
benzenephosphonic acid
phenylphosphonic acid
1571-33-1
phenylphosphonic acid, 98%
NCISTRUC1_000503
NCISTRUC2_000427
bdbm50162814
FT-0651791
CHEMBL179801 ,
phenyl-phosphonic acid
P0204
CHEBI:191118
A809812
4-16-00-01068 (beilstein handbook reference)
byd76t2868 ,
unii-byd76t2868
phosphonic acid, p-phenyl-
cas-1571-33-1
dtxcid0024399
NCGC00255888-01
tox21_302060
dtxsid2044399 ,
AKOS015889842
dihydrogen phenylphosphonate
SCHEMBL34998
phenyl phosphonic acid
phenylphosphonicacid
sv7 ,
phosphonic acid,phenyl-
mfcd00002136
J-009379
Q26841314
CS-0128808
doi:10.14272/qlzhniaadxejjp-uhfffaoysa-n.1
10.14272/QLZHNIAADXEJJP-UHFFFAOYSA-N.1

Research Excerpts

Effects

ExcerptReferenceRelevance
"Phenylphosphonic acid, which has been regarded the "epitope" of phosphotyrosine, was used as a template, and commercially available zinc acrylate was used as a functional monomer to prepare the MIP."( One-pot synthesis of phenylphosphonic acid imprinted polymers for tyrosine phosphopeptides recognition in aqueous phase.
Hu, Y; Li, Q; Ren, X; Shen, F; Xu, L; Zhang, Q; Zhang, X, 2013
)
1.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzenesAny benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives.
[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 (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 2Homo sapiens (human)Ki0.09900.00000.72369.9200AID238755
Carbonic anhydrase 4Homo sapiens (human)Ki5.40000.00021.97209.9200AID238915
Carbonic anhydrase 5A, mitochondrialHomo sapiens (human)Ki90.00000.00001.27259.9000AID239032
Carbonic anhydrase 9Homo sapiens (human)Ki2,210.00000.00010.78749.9000AID239054
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 1Homo sapiens (human)KA0.10000.02001.72197.4000AID238032
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
one-carbon metabolic processCarbonic anhydrase 1Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
bicarbonate transportCarbonic anhydrase 4Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 4Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
response to hypoxiaCarbonic anhydrase 9Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 9Homo sapiens (human)
response to xenobiotic stimulusCarbonic anhydrase 9Homo sapiens (human)
response to testosteroneCarbonic anhydrase 9Homo sapiens (human)
secretionCarbonic anhydrase 9Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
arylesterase activityCarbonic anhydrase 1Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 1Homo sapiens (human)
protein bindingCarbonic anhydrase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 1Homo sapiens (human)
hydro-lyase activityCarbonic anhydrase 1Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 1Homo sapiens (human)
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 4Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 4Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 4Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
zinc ion bindingCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 9Homo sapiens (human)
protein bindingCarbonic anhydrase 9Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 9Homo sapiens (human)
molecular function activator activityCarbonic anhydrase 9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (23)

Processvia Protein(s)Taxonomy
cytosolCarbonic anhydrase 1Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 1Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 4Homo sapiens (human)
rough endoplasmic reticulumCarbonic anhydrase 4Homo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartmentCarbonic anhydrase 4Homo sapiens (human)
Golgi apparatusCarbonic anhydrase 4Homo sapiens (human)
trans-Golgi networkCarbonic anhydrase 4Homo sapiens (human)
plasma membraneCarbonic anhydrase 4Homo sapiens (human)
external side of plasma membraneCarbonic anhydrase 4Homo sapiens (human)
cell surfaceCarbonic anhydrase 4Homo sapiens (human)
membraneCarbonic anhydrase 4Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 4Homo sapiens (human)
transport vesicle membraneCarbonic anhydrase 4Homo sapiens (human)
secretory granule membraneCarbonic anhydrase 4Homo sapiens (human)
brush border membraneCarbonic anhydrase 4Homo sapiens (human)
perinuclear region of cytoplasmCarbonic anhydrase 4Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 4Homo sapiens (human)
plasma membraneCarbonic anhydrase 4Homo sapiens (human)
mitochondrial matrixCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
cytoplasmCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
nucleolusCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
membraneCarbonic anhydrase 9Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 9Homo sapiens (human)
microvillus membraneCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID605761Inhibition of Escherichia coli recombinant DXR using DXP as substrate and MgCl2 as cofactor at 100 uM preincubated for 10 mins2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Inhibition of 1-deoxy-D-xylulose-5-phosphate reductoisomerase by lipophilic phosphonates: SAR, QSAR, and crystallographic studies.
AID238755Binding affinity towards human cytosolic carbonic anhydrase II2005Bioorganic & medicinal chemistry letters, Mar-15, Volume: 15, Issue:6
Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with organic phosphates and phosphonates.
AID605760Inhibition of Escherichia coli recombinant DXR using DXP as substrate and MgCl2 as cofactor preincubated for 10 mins2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Inhibition of 1-deoxy-D-xylulose-5-phosphate reductoisomerase by lipophilic phosphonates: SAR, QSAR, and crystallographic studies.
AID238032Activation constant towards human cytosolic carbonic anhydrase I; Activator2005Bioorganic & medicinal chemistry letters, Mar-15, Volume: 15, Issue:6
Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with organic phosphates and phosphonates.
AID239054Binding affinity owards recombinant human transmembrane carbonic anhydrase IX2005Bioorganic & medicinal chemistry letters, Mar-15, Volume: 15, Issue:6
Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with organic phosphates and phosphonates.
AID605841Inhibition of Mycobacterium tuberculosis recombinant DXR expressed in Escherichia coli BL21 (DE3) using DXP as substrate and MgCl2 as cofactor at 100 uM preincubated for 10 mins2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Inhibition of 1-deoxy-D-xylulose-5-phosphate reductoisomerase by lipophilic phosphonates: SAR, QSAR, and crystallographic studies.
AID239032Binding affinity towards recombinant human mitochondrial carbonic anhydrase V2005Bioorganic & medicinal chemistry letters, Mar-15, Volume: 15, Issue:6
Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with organic phosphates and phosphonates.
AID238915Binding affinity towards human membrane associated carbonic anhydrase IV2005Bioorganic & medicinal chemistry letters, Mar-15, Volume: 15, Issue:6
Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with organic phosphates and phosphonates.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (51)

TimeframeStudies, This Drug (%)All Drugs %
pre-199012 (23.53)18.7374
1990's9 (17.65)18.2507
2000's15 (29.41)29.6817
2010's15 (29.41)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: 35.84

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

MetricThis Compound (vs All)
Research Demand Index35.84 (24.57)
Research Supply Index3.97 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index45.47 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (35.84)

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%
Other52 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]