Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-01-30 09:50:05 UTC
Update Date2020-11-09 23:18:27 UTC
HMDB IDHMDB0011625
Secondary Accession Numbers
  • HMDB0094715
  • HMDB11625
  • HMDB94715
Metabolite Identification
Common NameDimethylarsinic acid
DescriptionDimethylarsinic acid, also known as cacodylic acid, is formally rated as possibly a carcinogenic (IARC 2B), potentially toxic compound. 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. Dimethylarsinic 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, dimethylarsinic acid does promote tumours in the presence of carcinogens in organs such as the kidneys and liver (Wikipedia ).
Structure
Data?1582752930
Synonyms
ValueSource
[As(CH3)2O(OH)]ChEBI
CACODYLIC ACIDChEBI
DimethylarsinateChEBI
KakodylsaeureChEBI
Me2as(=o)OHChEBI
CACODYLateGenerator
Acid, dimethylarsinicHMDB
Acid, cacodylicHMDB
As,as-dimethylarsinic acidHMDB
Dimethylarsenic acidHMDB
Hydroxydimethylarsine oxideHMDB
Dimethylarsinic acidGenerator
Chemical FormulaC2H7AsO2
Average Molecular Weight137.9974
Monoisotopic Molecular Weight137.966200885
IUPAC Namedimethylarsinic acid
Traditional Nameansar
CAS Registry Number75-60-5
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
Description 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

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available112.497http://allccs.zhulab.cn/database/detail?ID=AllCCS00001535
Predicted Molecular Properties
PropertyValueSource
Water Solubility90.2 g/LALOGPS
logP10(-0.48) g/LALOGPS
logP10(-0.33) g/LChemAxon
logS10(0.27) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dimethylarsinic acidC[As](C)(O)=O1639.3Standard polar33892256
Dimethylarsinic acidC[As](C)(O)=O915.8Standard non polar33892256
Dimethylarsinic acidC[As](C)(O)=O873.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dimethylarsinic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0900000000-aacd14a23122c6fead4f2017-09-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dimethylarsinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0596-6900000000-c094738db14b7209da382014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinic acid 10V, Negative-QTOFsplash10-00di-0900000000-4605296babdf6148fcc32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinic acid 20V, Negative-QTOFsplash10-00kr-5900000000-3be49b0b6e40807a58e42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinic acid 40V, Negative-QTOFsplash10-000i-0900000000-0b14088c1c17aff4669f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinic acid 10V, Negative-QTOFsplash10-000i-0900000000-723d8270a195a697561f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinic acid 20V, Negative-QTOFsplash10-000i-0900000000-0b6b8eda42b4b4a2c55e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinic acid 40V, Negative-QTOFsplash10-0gb9-0900000000-1ab81c1f902ad9956e3b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinic acid 10V, Positive-QTOFsplash10-000i-0900000000-277740f35cf8f3db10762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinic acid 20V, Positive-QTOFsplash10-000i-0900000000-3ba00e60d1b6e66786aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinic acid 40V, Positive-QTOFsplash10-000i-0900000000-8ae8b3e2664bfccfadce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinic acid 10V, Positive-QTOFsplash10-00di-0900000000-2f08307520e1e4ad4d1f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinic acid 20V, Positive-QTOFsplash10-00di-0900000000-6bc98922234d783edd282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinic acid 40V, Positive-QTOFsplash10-0udi-0900000000-d9daf50debedfc9ab8472021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
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 but not QuantifiedNot QuantifiedAdult (>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
UrineDetected and Quantified0.00328 (0.00303-0.00354) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.00391-0.00428 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02994
Phenol Explorer Compound IDNot Available
FooDB IDFDB028327
KNApSAcK IDC00033777
Chemspider ID2418
KEGG Compound IDC07308
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCacodylic_acid
METLIN IDNot Available
PubChem Compound2513
PDB IDNot Available
ChEBI ID48765
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yamanaka K, Mizol M, Kato K, Hasegawa A, Nakano M, Okada S: Oral administration of dimethylarsinic acid, a main metabolite of inorganic arsenic, in mice promotes skin tumorigenesis initiated by dimethylbenz(a)anthracene with or without ultraviolet B as a promoter. Biol Pharm Bull. 2001 May;24(5):510-4. [PubMed:11379771 ]
  2. Maki T, Hirota W, Motojima H, Hasegawa H, Rahman MA: Influence of aggregated particles on biodegradation activities for dimethylarsinic acid (DMA) in Lake Kahokugata. Chemosphere. 2011 Jun;83(11):1486-92. doi: 10.1016/j.chemosphere.2011.01.059. Epub 2011 Feb 20. [PubMed:21342701 ]

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 + Dimethylarsinic aciddetails