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Record Information
Version3.6
Creation Date2009-01-30 09:50:05 UTC
Update Date2016-02-11 01:21:49 UTC
HMDB IDHMDB11625
Secondary Accession NumbersNone
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
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 KeyInChIKey=OGGXGZAMXPVRFZ-UHFFFAOYSA-M
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pentavalent organic arsenic compounds. These are organoarsenic compounds in which a carbon is linked to a pentavalent arsenic atom.
KingdomOrganic compounds
Super ClassOrganometallic compounds
ClassOrganometalloid compounds
Sub ClassOrganoarsenic compounds
Direct ParentPentavalent organic arsenic compounds
Alternative Parents
Substituents
  • Pentavalent organic arsenic compound
  • Hydrocarbon derivative
  • Organic metalloid salt
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.78 m3·mol-1ChemAxon
Polarizability8.91 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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
NuGOwiki LinkHMDB11625
Metagene LinkHMDB11625
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