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Record Information
Version4.0
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 methanearsonateHMDB
Monomethylarsonic acid, ammonium, iron (3+) saltHMDB
Monomethylarsonic acid, dimercury (1+) saltHMDB
Monomethylarsonic acid, disodium saltHMDB
Monomethylarsonic acid, dipotassium saltHMDB
Monomethylarsonic acid, iron (2+) salt (3:2)HMDB
Monomethylarsonic acid, monoammonium saltHMDB
Monomethylarsonic acid, monosodium saltHMDB
Monomethylarsonic acid, zinc saltHMDB
Methylarsonous acidHMDB
Monomethylarsonic acid, iron saltHMDB
Monomethylarsonic acid, monocalcium saltHMDB
MSMAHMDB
Monomethylarsonic acid, calcium salt (2:1)HMDB
Monosodium methanearsonateHMDB
Sodium methanearsonateHMDB
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
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0900000000-da4d5da1a88bf0f506f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-f551e617364ce9ae8012Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-2b6d3fe988a733ee8b82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0900000000-5b1e291e8a048e93b1bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0900000000-faba21d1399d2be5f4ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-3900000000-c63ab6bc2dbdb52cf07fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-0900000000-af38e8044b6fdf1533a7Spectrum
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
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