Survey with prize
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Showing metabocard for Methylarsonite (HMDB0012259)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:54 UTC
Update Date2020-02-26 21:37:14 UTC
HMDB IDHMDB0012259
Secondary Accession Numbers
  • HMDB12259
Metabolite Identification
Common NameMethylarsonite
DescriptionMethylarsonite, also known as meas(OH)2 or mma(iii), belongs to the class of organic compounds known as trivalent organic arsenic compounds. These are organoarsenic compounds in which a carbon is linked to a trivalent arsenic atom. A one-carbon compound that is arsonous acid in which the hydrogen attached to arsenic is replaced by a methyl group. Methylarsonite is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, methylarsonite participates in a number of enzymatic reactions. In particular, methylarsonite and oxidized glutathione can be biosynthesized from methylarsonate and glutathione through the action of the enzyme glutathione S-transferase omega-1. In addition, methylarsonite and S-adenosylmethionine can be converted into dimethylarsinate and S-adenosylhomocysteine; which is catalyzed by the enzyme arsenite methyltransferase. In humans, methylarsonite is involved in arsenate detoxification.
Structure
Data?1582753034
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
MeAs(OH)2ChEBI
Methanearsonous acidChEBI
Mma(III)ChEBI
MMAIIIChEBI
Monomethylarsenous acidChEBI
Monomethylarsonous acidChEBI
Methyl arsonous acidHMDB
Methylarsonous acidHMDB
MethylarsoniteChEBI
Chemical FormulaCH5AsO2
Average Molecular Weight123.9708
Monoisotopic Molecular Weight123.950550821
IUPAC Namemethylarsonous acid
Traditional Namemethylarsonous acid
CAS Registry Number25400-23-1
SMILES
C[As](O)O
InChI Identifier
InChI=1S/CH5AsO2/c1-2(3)4/h3-4H,1H3
InChI KeyOXBIRPQQKCQWGV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as trivalent organic arsenic compounds. These are organoarsenic compounds in which a carbon is linked to a trivalent arsenic atom.
KingdomOrganic compounds
Super ClassOrganometallic compounds
ClassOrganometalloid compounds
Sub ClassOrganoarsenic compounds
Direct ParentTrivalent organic arsenic compounds
Alternative Parents
Substituents
  • Trivalent organic arsenic compound
  • Organoarsonous acid
  • Oxygen-containing organoarsenic compound
  • Organic metalloid salt
  • Organic oxygen compound
  • Organopnictogen compound
  • 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 Solubility708 g/LALOGPS
logP-0.9ALOGPS
logP-1ChemAxon
logS0.76ALOGPS
pKa (Strongest Acidic)8.65ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity11.07 m³·mol⁻¹ChemAxon
Polarizability7.34 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, Positivesplash10-0a4i-0900000000-918a2f74d7a06f030bdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-3c1ffe084e9cde17253cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-f5c1555d242b5cfb66dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1900000000-9ca9523309b2398cace9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0900000000-7d39868bc634bbb4eed9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-3900000000-4a208e1f8bbc2408905aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0900000000-3436bb44a28cdbfdb073Spectrum
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 IDFDB028898
KNApSAcK IDNot Available
Chemspider ID141846
KEGG Compound IDC07295
BioCyc IDMETHYLARSONITE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound161491
PDB IDNot Available
ChEBI ID17826
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Arsenite methyltransferase
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 + Methylarsonite → S-Adenosylhomocysteine + Dimethylarsinic aciddetails
Enzyme Details
2. Glutathione S-transferase omega-1
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
Enzyme Details
3. Glutathione S-transferase omega-2
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