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Human Metabolome Database Version 3.5

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Showing metabocard for Dimethylarsinous acid (HMDB12216)

Record Information
Version 3.5
Creation Date 2009-04-06 10:21:10 -0600
Update Date 2013-05-29 13:47:48 -0600
HMDB ID HMDB12216
Secondary Accession Numbers None
Metabolite Identification
Common Name Dimethylarsinous acid
Description Dimethylarsinous 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 Link_out).
Structure Thumb
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Synonyms
  1. Dimethylarsinite
  2. Dimethylarsinous-acid
  3. DmaIII
  4. Me2AsOH
  5. [As(CH3)2(OH)]
Chemical Formula C2H7AsO
Average Molecular Weight 121.998
Monoisotopic Molecular Weight 121.971286263
IUPAC Name dimethylarsinous acid
Traditional IUPAC Name dimethylarsinous acid
CAS Registry Number 55094-22-9
SMILES C[As](C)O
InChI Identifier InChI=1S/C2H7AsO/c1-3(2)4/h4H,1-2H3
InChI Key VDEGQTCMQUFPFH-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organometallic Compounds
Class N/A
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Metalloid Compounds
  • Organoarsenic Compounds
  • a small molecule(Cyc)
  • methylarsinous acid(ChEBI)
Substituents
  • N/A
Direct Parent Organometallic Compounds
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 133 g/L ALOGPS
LogP -0.14 ALOGPS
LogP 0.62 ChemAxon
LogS 0.04 ALOGPS
pKa (strongest acidic) 12.64 ChemAxon
pKa (strongest basic) -3.8 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 14.12 ChemAxon
Polarizability 8.37 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028860
KNApSAcK ID Not Available
Chemspider ID 161508 Link_out
KEGG Compound ID C20300 Link_out
BioCyc ID DIMETHYLARSINOUS-ACID Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12216 Link_out
Metagene Link HMDB12216 Link_out
METLIN ID Not Available
PubChem Compound 185792 Link_out
PDB ID Not Available
ChEBI ID 23808 Link_out
References
Synthesis Reference Not 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 Link_out