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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:10 UTC
Update Date2020-02-26 21:37:08 UTC
HMDB IDHMDB0012216
Secondary Accession Numbers
  • HMDB12216
Metabolite Identification
Common NameDimethylarsinous acid
DescriptionDimethylarsinous acid is a reactive organic intermediate of dimethylarsinic acid involved in toxicity. Dimethylarsinous acid is detected in the urine of individuals who ingest arsenic-polluted drinking water. The cytogenetic study in V79 cells using iododimethylarsine, which is easily hydrolyzed to dimethylarsinous acid in water, revealed that dimethylarsinous acid was very cytotoxic (50% growth inhibition concentration; 1.1 (+-) 0.14 uM), and either induced aneuploids or a high rate of tetraploids (73% at 2.5 μM). Dimethylarsinous acid caused mitotic arrest, since the mitotic index at toxic dose (5 μM) was 13.9%, significantly higher than the control (2.7%). Dimethylarsinous acid significantly increased sister chromatid exchange (SCE) and chromosomal aberrations, most of which were chromatid gaps and chromatid breaks. The cytotoxicity and the activity of dimethylarsinous acid in inducing chromosomal aberration or SCE was as effective as arsenite, but the activity was much lower than that of mitomycin C, which was used as a positive control. The most potent effects of dimethylarsinous acid on the cells were induction of aneuploids, tetraploids and c-mitosis. The toxicity of dimethylarsinous acid is strongly related to the disturbance of the normal cell cycle.(PMID: 15276414 ).
Structure
Data?1582753028
Synonyms
ValueSource
[As(CH3)2(OH)]ChEBI
Me2asohChEBI
DimethylarsiniteHMDB
Dimethylarsinous-acidHMDB
DmaIIIHMDB
Chemical FormulaC2H7AsO
Average Molecular Weight121.998
Monoisotopic Molecular Weight121.971286263
IUPAC Namedimethylarsinous acid
Traditional Namedimethylarsinous acid
CAS Registry Number55094-22-9
SMILES
C[As](C)O
InChI Identifier
InChI=1S/C2H7AsO/c1-3(2)4/h4H,1-2H3
InChI KeyVDEGQTCMQUFPFH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organoarsinous acids. These are as-hydrocarbyl compounds with the general formula R2As(OH), where R is an organic group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganoarsinous acids
Sub ClassNot Available
Direct ParentOrganoarsinous acids
Alternative Parents
Substituents
  • Organoarsinous acid
  • Trivalent organic arsenic compound
  • Oxygen-containing organoarsenic compound
  • Organic metalloid salt
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organoarsenic compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

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 Solubility133 g/LALOGPS
logP-0.14ALOGPS
logP0.62ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)12.64ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.12 m³·mol⁻¹ChemAxon
Polarizability8.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-0900000000-c426540232d82e0071e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-558a3956761d64537affSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-add81bc9740760fb68f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0900000000-d2384f3218994078ecbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-1900000000-5b0db65487faceff958fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-4900000000-78205e78a4be068dd635Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0900000000-94f4ee023d5192098af4Spectrum
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 IDFDB028860
KNApSAcK IDNot Available
Chemspider ID161508
KEGG Compound IDC20300
BioCyc IDDIMETHYLARSINOUS-ACID
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound185792
PDB IDNot Available
ChEBI ID23808
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kuroda K, Yoshida K, Yoshimura M, Endo Y, Wanibuchi H, Fukushima S, Endo G: Microbial metabolite of dimethylarsinic acid is highly toxic and genotoxic. Toxicol Appl Pharmacol. 2004 Aug 1;198(3):345-53. [PubMed:15276414 ]