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Showing metabocard for Dimethylarsinous acid (HMDB0012216)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:10 UTC
Update Date2023-02-21 17:17:44 UTC
HMDB IDHMDB0012216
Secondary Accession Numbers
  • HMDB12216
Metabolite Identification
Common NameDimethylarsinous acid
DescriptionDimethylarsinous 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 ).
Structure
Data?1676999864
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012216 (Dimethylarsinous acid)


  Mrv0541 02241203502D          

  4  3  0  0  0  0            999 V2000
   14.1046  -11.1525    0.0000 As  0  0  0  0  0  0  0  0  0  0  0  0
   14.9297  -11.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6921  -10.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6921  -11.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
M  END
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3D MOL for HMDB0012216 (Dimethylarsinous acid)

HMDB0012216
     RDKit          3D
Dimethylarsinous acid
 11 10  0  0  0  0  0  0  0  0999 V2000
    1.6934   -0.4195   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0308    0.2788   -0.5883 As  0  0  0  0  0  3  0  0  0  0  0  0
   -1.5326   -0.6183    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0960    2.0731   -0.2163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7882   -1.5126   -0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.0059   -0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -0.0301    0.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4679   -0.2513   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5176   -1.7050    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6152   -0.3050    1.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6772    2.4842   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  3  8  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
M  END
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3D SDF for HMDB0012216 (Dimethylarsinous acid)


  Mrv0541 02241203502D          

  4  3  0  0  0  0            999 V2000
   14.1046  -11.1525    0.0000 As  0  0  0  0  0  0  0  0  0  0  0  0
   14.9297  -11.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6921  -10.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6921  -11.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012216

> <DATABASE_NAME>
hmdb

> <SMILES>
C[As](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C2H7AsO/c1-3(2)4/h4H,1-2H3

> <INCHI_KEY>
VDEGQTCMQUFPFH-UHFFFAOYSA-N

> <FORMULA>
C2H7AsO

> <MOLECULAR_WEIGHT>
121.998

> <EXACT_MASS>
121.971286263

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
8.368745097851708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
dimethylarsinous acid

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
0.6160000000000001

> <ALOGPS_LOGS>
0.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.641494379493459

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8304103584095612

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
14.1248

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethylarsinous acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0012216 (Dimethylarsinous acid)

HMDB0012216
     RDKit          3D
Dimethylarsinous acid
 11 10  0  0  0  0  0  0  0  0999 V2000
    1.6934   -0.4195   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0308    0.2788   -0.5883 As  0  0  0  0  0  3  0  0  0  0  0  0
   -1.5326   -0.6183    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0960    2.0731   -0.2163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7882   -1.5126   -0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.0059   -0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -0.0301    0.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4679   -0.2513   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5176   -1.7050    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6152   -0.3050    1.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6772    2.4842   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  3  8  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
M  END
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PDB for HMDB0012216 (Dimethylarsinous acid)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 As   UNK     0      26.329 -20.818   0.000  0.00  0.00          As+0
HETATM    2  O   UNK     0      27.869 -20.818   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      25.559 -19.484   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.559 -22.152   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for HMDB0012216 (Dimethylarsinous acid)

COMPND    HMDB0012216
HETATM    1  C1  UNL     1       1.693  -0.420  -0.011  1.00  0.00           C  
HETATM    2 AS1  UNL     1      -0.031   0.279  -0.588  1.00  0.00          AS  
HETATM    3  C2  UNL     1      -1.533  -0.618   0.280  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.096   2.073  -0.216  1.00  0.00           O  
HETATM    5  H1  UNL     1       1.788  -1.513  -0.092  1.00  0.00           H  
HETATM    6  H2  UNL     1       2.470   0.006  -0.709  1.00  0.00           H  
HETATM    7  H3  UNL     1       1.986  -0.030   0.998  1.00  0.00           H  
HETATM    8  H4  UNL     1      -2.468  -0.251  -0.220  1.00  0.00           H  
HETATM    9  H5  UNL     1      -1.518  -1.705   0.137  1.00  0.00           H  
HETATM   10  H6  UNL     1      -1.615  -0.305   1.340  1.00  0.00           H  
HETATM   11  H7  UNL     1      -0.677   2.484  -0.915  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    4
CONECT    3    8    9   10
CONECT    4   11
END
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SMILES for HMDB0012216 (Dimethylarsinous acid)

C[As](C)O
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INCHI for HMDB0012216 (Dimethylarsinous acid)

InChI=1S/C2H7AsO/c1-3(2)4/h4H,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
[As(CH3)2(OH)]ChEBI
Me2asohChEBI
DimethylarsiniteHMDB, MeSH
Dimethylarsinous-acidHMDB
DmaIIIHMDB
Chemical FormulaC2H7AsO
Average Molecular Weight121.998
Monoisotopic Molecular Weight121.971286263
IUPAC Namedimethylarsinous acid
Traditional Namedimethylarsinous acid
CAS Registry Number55094-22-9
SMILES
C[As](C)O
InChI Identifier
InChI=1S/C2H7AsO/c1-3(2)4/h4H,1-2H3
InChI KeyVDEGQTCMQUFPFH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organoarsinous acids. These are as-hydrocarbyl compounds with the general formula R2As(OH), where R is an organic group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganoarsinous acids
Sub ClassNot Available
Direct ParentOrganoarsinous acids
Alternative Parents
Substituents
  • Organoarsinous acid
  • Trivalent organic arsenic compound
  • Oxygen-containing organoarsenic compound
  • Organic metalloid salt
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organoarsenic compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility133 g/LALOGPS
logP-0.14ALOGPS
logP0.62ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)12.64ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.12 m³·mol⁻¹ChemAxon
Polarizability8.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+112.032859911
AllCCS[M+H-H2O]+108.132859911
AllCCS[M+NH4]+115.732859911
AllCCS[M+Na]+116.832859911
AllCCS[M-H]-173.432859911
AllCCS[M+Na-2H]-180.032859911
AllCCS[M+HCOO]-187.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dimethylarsinous acidC[As](C)O830.3Standard polar33892256
Dimethylarsinous acidC[As](C)O660.6Standard non polar33892256
Dimethylarsinous acidC[As](C)O667.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dimethylarsinous acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-0900000000-c426540232d82e0071e12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dimethylarsinous acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinous acid 10V, Positive-QTOFsplash10-00di-0900000000-558a3956761d64537aff2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinous acid 20V, Positive-QTOFsplash10-00di-0900000000-add81bc9740760fb68f92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinous acid 40V, Positive-QTOFsplash10-00di-0900000000-d2384f3218994078ecbd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinous acid 10V, Negative-QTOFsplash10-0uk9-1900000000-5b0db65487faceff958f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinous acid 20V, Negative-QTOFsplash10-00xr-4900000000-78205e78a4be068dd6352015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinous acid 40V, Negative-QTOFsplash10-00di-0900000000-94f4ee023d5192098af42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinous acid 10V, Negative-QTOFsplash10-00di-0900000000-d965880a8b34eca523102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinous acid 20V, Negative-QTOFsplash10-00di-0900000000-9a11567c8528a3acbe8e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinous acid 40V, Negative-QTOFsplash10-0uk9-0900000000-4ca751f4be206f62a72d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinous acid 10V, Positive-QTOFsplash10-0uk9-0900000000-09f768ab94de685549842021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinous acid 20V, Positive-QTOFsplash10-00di-0900000000-8098e86b9bcd4fe79aa12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylarsinous acid 40V, Positive-QTOFsplash10-0pb9-0900000000-4516589ec663d284548d2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028860
KNApSAcK IDNot Available
Chemspider ID161508
KEGG Compound IDC20300
BioCyc IDDIMETHYLARSINOUS-ACID
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound185792
PDB IDNot Available
ChEBI ID23808
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. 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 ]