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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:53 UTC
Update Date2020-02-26 21:37:14 UTC
HMDB IDHMDB0012258
Secondary Accession Numbers
  • HMDB0011682
  • HMDB11682
  • HMDB12258
Metabolite Identification
Common NameMethylarsonate
DescriptionMethylarsonate is used as a contact herbicide in either the monosodium or disodium salt form. It goes by the trade names Weed-E-Rad, Ansar 170 H.C., Ansar 529 H.C., DiTac and others. Methylarsonate is considered only slightly toxic, having an oral LD50 of 2200 mg/Kg for rats. The inhalation risk is greater with LD50 Rats >20 mg. Long term studies with people exposed to organoarsenicals has shown an increased risk of skin cancer (Spiewak, 2001), lung cancer and some liver cancers, although some recent studies have shown some arsenic containing compounds (specifically Arsine trioxide) may have anticarcinogenic properties (Wang, 2001). In mammals, Methylarsonate is also an intermediate in the detoxification of inorganic arsenic. In the arsenate detoxification I pathway, arsenite reacts with S-adenosyl-L-methionine to produce methylarsonate and S-adenosyl-L-homocysteine. Arsenite methyltransferase catalyzes this reaction. Methylarsonate then reacts with 2 glutathione molecules to produce glutathione disulfide and methylarsonite. This reaction is catalyzed by methylarsonate reductase. Methylarsonate is an organic arsenic compound with adverse effects similar to those of arsenic trioxide. Arsenic is found in the environment primarily as arsenate and arsenite species. Arsenate is reduced to arsenite by arsenate reductase and can be subsequently methylated to Methylarsonate. This is then reduced and methylated to Dimethylarsinate, which can excreted and is considerably less toxic to the organism than any of the previous intermediate compounds. Methylarsonate was formerly included in some vitamin and mineral preparations. It was once used to treat tuberculosis, chorea, and other affections in which the cacodylates were used.
Structure
Data?1582753034
Synonyms
ValueSource
MAAChEBI
MeAsO(OH)2ChEBI
Methanearsonic acidChEBI
Monomethylarsonic acidChEBI
Methylarsonic acidKegg
MethanearsonateGenerator
MonomethylarsonateGenerator
Dsma (jmaf)HMDB
Kyselina methylarsonovaHMDB
Methyl arsonic acidHMDB
Methylarsenic acidHMDB
Methylarsinic acidHMDB
Monomethylarsinic acidHMDB
Disodium methanearsonateMeSH, HMDB
Monomethylarsonic acid, ammonium, iron (3+) saltMeSH, HMDB
Monomethylarsonic acid, dimercury (1+) saltMeSH, HMDB
Monomethylarsonic acid, disodium saltMeSH, HMDB
Monomethylarsonic acid, dipotassium saltMeSH, HMDB
Monomethylarsonic acid, iron (2+) salt (3:2)MeSH, HMDB
Monomethylarsonic acid, monoammonium saltMeSH, HMDB
Monomethylarsonic acid, monosodium saltMeSH, HMDB
Monomethylarsonic acid, zinc saltMeSH, HMDB
Methylarsonous acidMeSH, HMDB
Monomethylarsonic acid, iron saltMeSH, HMDB
Monomethylarsonic acid, monocalcium saltMeSH, HMDB
MSMAMeSH, HMDB
Monomethylarsonic acid, calcium salt (2:1)MeSH, HMDB
Monosodium methanearsonateMeSH, HMDB
Sodium methanearsonateMeSH, HMDB
Chemical FormulaCH5AsO3
Average Molecular Weight139.9702
Monoisotopic Molecular Weight139.945465443
IUPAC Namemethylarsonic acid
Traditional Namemonomethylarsonic acid
CAS Registry Number124-58-3
SMILES
C[As](O)(O)=O
InChI Identifier
InChI=1S/CH5AsO3/c1-2(3,4)5/h1H3,(H2,3,4,5)
InChI KeyQYPPRTNMGCREIM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pentaorganoarsanes. These are organoarsenic compounds containing an arsenic compound that is pentasubstituted by only organic groups.
KingdomOrganic compounds
Super ClassOrganometallic compounds
ClassOrganometalloid compounds
Sub ClassOrganoarsenic compounds
Direct ParentPentaorganoarsanes
Alternative Parents
Substituents
  • Pentaorganoarsane
  • Alkylarsine oxide
  • Oxygen-containing organoarsenic compound
  • Organic metalloid salt
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility569 g/LALOGPS
logP-1ALOGPS
logP-0.91ChemAxon
logS0.61ALOGPS
pKa (Strongest Acidic)4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity11.9 m³·mol⁻¹ChemAxon
Polarizability8.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+118.232859911
AllCCS[M+H-H2O]+114.332859911
AllCCS[M+NH4]+121.932859911
AllCCS[M+Na]+122.932859911
AllCCS[M-H]-154.032859911
AllCCS[M+Na-2H]-159.432859911
AllCCS[M+HCOO]-165.432859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methylarsonate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0900000000-da4d5da1a88bf0f506f42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylarsonate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonate 10V, Positive-QTOFsplash10-0006-0900000000-f551e617364ce9ae80122016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonate 20V, Positive-QTOFsplash10-0006-0900000000-2b6d3fe988a733ee8b822016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonate 40V, Positive-QTOFsplash10-0006-0900000000-5b1e291e8a048e93b1bb2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonate 10V, Negative-QTOFsplash10-00dr-0900000000-faba21d1399d2be5f4cc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonate 20V, Negative-QTOFsplash10-000i-3900000000-c63ab6bc2dbdb52cf07f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonate 40V, Negative-QTOFsplash10-0079-0900000000-af38e8044b6fdf1533a72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonate 10V, Positive-QTOFsplash10-0fk9-0900000000-5b44146ed9e26a03f3f02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonate 20V, Positive-QTOFsplash10-006x-0900000000-f2dd94a490343ba798102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonate 40V, Positive-QTOFsplash10-00di-0900000000-59b264953374dcd1e76a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonate 10V, Negative-QTOFsplash10-000i-0900000000-387eed30d629c4fb05692021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonate 20V, Negative-QTOFsplash10-000i-0900000000-59b86cdf1af4cd9c10482021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonate 40V, Negative-QTOFsplash10-00dr-0900000000-2b854fae760c89475df52021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028897
KNApSAcK IDNot Available
Chemspider ID8604
KEGG Compound IDC07294
BioCyc IDMETHYLARSONATE
BiGG IDNot Available
Wikipedia LinkMethylarsonic acid
METLIN IDNot Available
PubChem Compound8948
PDB IDNot Available
ChEBI ID29852
Food Biomarker OntologyNot Available
VMH IDM02474
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Catalyzes the transfer of a methyl group from AdoMet to trivalent arsenicals producing methylated and dimethylated arsenicals. It methylates arsenite to form methylarsonate, Me-AsO(3)H(2), which is reduced by methylarsonate reductase to methylarsonite, Me-As(OH)2. Methylarsonite is also a substrate and it is converted into the much less toxic compound dimethylarsinate (cacodylate), Me(2)As(O)-OH (By similarity).
Gene Name:
AS3MT
Uniprot ID:
Q9HBK9
Molecular weight:
41747.49
Reactions
S-Adenosylmethionine + Arsenite → S-Adenosylhomocysteine + Methylarsonatedetails
General function:
Involved in glutathione transferase activity
Specific function:
Exhibits glutathione-dependent thiol transferase and dehydroascorbate reductase activities. Has S-(phenacyl)glutathione reductase activity. Has also glutathione S-transferase activity. Participates in the biotransformation of inorganic arsenic and reduces monomethylarsonic acid (MMA) and dimethylarsonic acid.
Gene Name:
GSTO1
Uniprot ID:
P78417
Molecular weight:
27565.6
Reactions
Methylarsonate + Glutathione → Methylarsonite + Oxidized glutathione + Waterdetails
General function:
Involved in glutathione transferase activity
Specific function:
Exhibits glutathione-dependent thiol transferase activity. Has high dehydroascorbate reductase activity and may contribute to the recycling of ascorbic acid. Participates in the biotransformation of inorganic arsenic and reduces monomethylarsonic acid (MMA).
Gene Name:
GSTO2
Uniprot ID:
Q9H4Y5
Molecular weight:
24399.09
Reactions
Methylarsonate + Glutathione → Methylarsonite + Oxidized glutathione + Waterdetails