Page last updated: 2024-11-05

methylphosphonic acid

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

Description

methylphosphonic acid : A one-carbon compound that is phosphonic acid in which the hydrogen attached to the phosphorus is substituted by a methyl group. [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 CID13818
CHEMBL ID122938
CHEBI ID45129
MeSH IDM0101714

Synonyms (38)

Synonym
unii-329w4ym10z
ai3-51156
einecs 213-607-2
ec 213-607-2
329w4ym10z ,
phosphonic acid, p-methyl-
nsc 119358
hsdb 6762
phosphonic acid, methyl-
methanephosphonic acid
993-13-5
nsc-119358
methylphosphonic acid
nsc119358
vxa ,
phosphonomethyl group
CHEBI:45129 ,
methyl phosphonic acid
methylphosphonic acid, 98%
bdbm50131862
L000171
CHEMBL122938 ,
methyl-phosphonic acid
methyl phosphonate
C20396
FT-0628284
AM20120404
AKOS017343694
methyl phosphonic acid [hsdb]
dihydrogen methylphosphonate
DTXSID5047748
57H ,
mfcd00002137
J-522698
methylphosphonic acid, 99.0-101.0% (t)
Q15634110
p-methylphosphonic acid
D95909

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Pharmacokinetic data allow one to determine the frequency of administration and any potential toxicity associated with chronic administration."( Pharmacokinetics of oligonucleotides.
Agrawal, S; Zhang, R, 1997
)
0.3

Dosage Studied

ExcerptRelevanceReference
" The oral route of drug dosing offers many advantages over other possible routes when chronic drug administration is necessary."( Radiolabeling of methylphosphonate and phosphorothioate oligonucleotides and evaluation of their transport in everted rat jejunum sacs.
Avrutskaya, AV; Brouwer, KL; Hughes, JA; Juliano, RL; Wickstrom, E, 1995
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
phosphonic acidsHP(=O)(OH)2 (phosphonic acid) and its P-substituted derivatives.
one-carbon compoundAn organic molecular entity containing a single carbon atom (C1).
[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]

Pathways (1)

PathwayProteinsCompounds
Methylphosphonate Degradation I711

Protein Targets (8)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 2Homo sapiens (human)Ki0.09800.00000.72369.9200AID238755
Carbonic anhydrase 4Homo sapiens (human)Ki310.00000.00021.97209.9200AID238915
Carbonic anhydrase 5A, mitochondrialHomo sapiens (human)Ki110.00000.00001.27259.9000AID239032
Carbonic anhydrase 9Homo sapiens (human)Ki1,260.00000.00010.78749.9000AID239054
[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)KA1.20000.02001.72197.4000AID238032
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

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)
dephosphorylationAlkaline phosphatase, germ cell typeHomo 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)
defense responseProtein tyrosine phosphatase receptor type C-associated proteinHomo 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 (9)

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)
alkaline phosphatase activityAlkaline phosphatase, germ cell typeHomo sapiens (human)
metal ion bindingAlkaline phosphatase, germ cell typeHomo 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)
protein bindingProtein tyrosine phosphatase receptor type C-associated proteinHomo 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 (25)

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)
extracellular regionAlkaline phosphatase, germ cell typeHomo sapiens (human)
plasma membraneAlkaline phosphatase, germ cell typeHomo sapiens (human)
side of membraneAlkaline phosphatase, germ cell typeHomo sapiens (human)
plasma membraneAlkaline phosphatase, germ cell typeHomo 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)
plasma membraneProtein tyrosine phosphatase receptor type C-associated proteinHomo sapiens (human)
plasma membraneProtein tyrosine phosphatase receptor type C-associated proteinHomo 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 (11)

Assay IDTitleYearJournalArticle
AID159822Inhibition of Human Placental alkaline Phosphatase (PLAP)2003Journal of medicinal chemistry, Aug-14, Volume: 46, Issue:17
A comparison of phosphonothioic acids with phosphonic acids as phosphatase inhibitors.
AID233500The pKa value was measured at 31-P chemical shift changes due to protonation1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
Protonation of phosphoramide mustard and other phosphoramides.
AID99563Inhibitory activity against Serine/Threonine Protein Phosphatase (Lambda protein phosphatase)2003Journal of medicinal chemistry, Aug-14, Volume: 46, Issue:17
A comparison of phosphonothioic acids with phosphonic acids as phosphatase inhibitors.
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.
AID213547Inhibitory activity against Tyrosine phosphatase from Yersinia (Yop protein)2003Journal of medicinal chemistry, Aug-14, Volume: 46, Issue:17
A comparison of phosphonothioic acids with phosphonic acids as phosphatase inhibitors.
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.
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.
AID32833Inhibitory activity against Escherichia coli Alkaline Phosphatase; no inhibition2003Journal of medicinal chemistry, Aug-14, Volume: 46, Issue:17
A comparison of phosphonothioic acids with phosphonic acids as phosphatase inhibitors.
AID164683Inhibitory activity against Serine/Threonine Protein phosphatase 2C (PP2C)2003Journal of medicinal chemistry, Aug-14, Volume: 46, Issue:17
A comparison of phosphonothioic acids with phosphonic acids as phosphatase inhibitors.
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.
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 (229)

TimeframeStudies, This Drug (%)All Drugs %
pre-199016 (6.99)18.7374
1990's69 (30.13)18.2507
2000's77 (33.62)29.6817
2010's53 (23.14)24.3611
2020's14 (6.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 41.30

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 Index41.30 (24.57)
Research Supply Index5.49 (2.92)
Research Growth Index4.99 (4.65)
Search Engine Demand Index60.99 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (41.30)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews10 (4.13%)6.00%
Case Studies2 (0.83%)4.05%
Observational0 (0.00%)0.25%
Other230 (95.04%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]