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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-01-30 09:50:05 UTC
Update Date2018-05-20 20:22:50 UTC
HMDB IDHMDB0011625
Secondary Accession Numbers
  • HMDB11625
Metabolite Identification
Common NameDimethylarsinate
DescriptionCacodylic acid is the chemical compound with the formula (CH3)2AsO2H. Derivatives of cacodylic acid, cacodylates, were frequently used as herbicides. For example, "Agent Blue," one of the chemicals used during the Vietnam War, is a mixture of cacodylic acid and sodium cacodylate. Sodium cacodylate is frequently used as a buffering agent in the preparation and fixation of biological samples for transmission electron microscopy. Cacodylic acid is highly toxic by ingestion, inhalation, or skin contact. Once thought to be a byproduct of inorganic arsenic detoxification, it is now believed to have serious health consequences of its own. It has been shown to be teratogenic in rodents, most often causing cleft palate but also fetal fatality at high doses. It has been shown to be genotoxic in human cells, causing apoptosis and also decreased DNA production and shorter DNA strands. While not itself a strong carcinogen, cacodylic acid does promote tumors in the presence of carcinogens in organs such as the kidneys and liver. (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
[As(CH3)2O(OH)]ChEBI
CACODYLIC ACIDChEBI
KakodylsaeureChEBI
Me2as(=o)OHChEBI
Dimethylarsinic acidGenerator
CACODYLateGenerator
Acid, dimethylarsinicMeSH
Acid, cacodylicMeSH
Chemical FormulaC2H7AsO2
Average Molecular Weight137.9974
Monoisotopic Molecular Weight137.966200885
IUPAC Namedimethylarsinic acid
Traditional Nameansar
CAS Registry Number15132-04-4
SMILES
C[As](C)(O)=O
InChI Identifier
InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)
InChI KeyOGGXGZAMXPVRFZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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:

Role

Industrial application:

Environmental role:

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 Solubility90.2 g/LALOGPS
logP-0.48ALOGPS
logP-0.33ChemAxon
logS0.27ALOGPS
pKa (Strongest Acidic)6.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity15.9 m³·mol⁻¹ChemAxon
Polarizability9.18 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0900000000-aacd14a23122c6fead4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-277740f35cf8f3db1076View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-3ba00e60d1b6e66786aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-8ae8b3e2664bfccfadceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-4605296babdf6148fcc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-5900000000-3be49b0b6e40807a58e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0900000000-0b14088c1c17aff4669fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0596-6900000000-c094738db14b7209da38View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    SalivaDetected and Quantified0.005 (0.0-0.018) uMAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.022 +/- 0.00095 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.00328 (0.00303-0.00354) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
    UrineDetected and Quantified0.00391 (0.00356-0.00428) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDDB02994
    Phenol Explorer Compound IDNot Available
    FoodDB IDNot Available
    KNApSAcK IDC00033777
    Chemspider IDNot Available
    KEGG Compound IDC07308
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkCacodylic_acid
    METLIN IDNot Available
    PubChem Compound2513
    PDB IDNot Available
    ChEBI ID48765
    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 + Methylarsonite → S-Adenosylhomocysteine + Dimethylarsinatedetails