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Record Information
Version4.0
Creation Date2009-01-30 09:50:05 UTC
Update Date2017-09-27 08:26:36 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)2O2](-)ChEBI
CACODYLATE ionChEBI
DMAChEBI
KakodylatChEBI
Me2aso2(-)ChEBI
Dimethylarsinic acidGenerator
CACODYLic acid ionGenerator
AnsarHMDB
ArsanHMDB
BolateHMDB
BollsHMDB
CacodylateHMDB
Cacodylic acidHMDB
ChexmateHMDB
DMAAHMDB
EraseHMDB
Hydroxydimethylarsine oxideHMDB
MoncideHMDB
PhytarHMDB
Phytar 560HMDB
SilvisarHMDB
Acid, dimethylarsinicMeSH
Acid, cacodylicMeSH
Chemical FormulaC2H6AsO2
Average Molecular Weight136.9894
Monoisotopic Molecular Weight136.958375853
IUPAC Namedimethylarsinate
Traditional Namecacodylate ion
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)/p-1
InChI KeyOGGXGZAMXPVRFZ-UHFFFAOYSA-M
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
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Role

Industrial application:

  Pharmaceutical industry:

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-0.07ALOGPS
logP-0.33ChemAxon
logS-0.24ALOGPS
pKa (Strongest Acidic)6.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.78 m³·mol⁻¹ChemAxon
Polarizability8.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-d533cd56f8170e4be583View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-e95617c0b139aab0a372View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-d470b06aa4343db66b99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-0900000000-83fefe4861ef23524d98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9400000000-99e10278db94eda7e6afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0900000000-567a2b0b9a278c491de7View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB028327
    KNApSAcK IDNot Available
    Chemspider ID146326
    KEGG Compound IDC07308
    BioCyc IDDIMETHYLARSINATE
    BiGG IDNot Available
    Wikipedia LinkCacodylic acid
    METLIN IDNot Available
    PubChem Compound167250
    PDB IDCAC
    ChEBI ID16223
    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