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Showing NP-Card for Dimethylarsinous acid (NP0091979)

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Record Information
Version2.0
Created at2022-05-11 18:53:46 UTC
Updated at2022-05-11 18:53:46 UTC
NP-MRD IDNP0091979
Secondary Accession NumbersNone
Natural Product Identification
Common NameDimethylarsinous acid
DescriptionDimethylarsinous acid, also known as [as(CH3)2(OH)] or ME2ASOH, 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. Dimethylarsinous acid is an extremely weak basic (essentially neutral) compound (based on its pKa). The most potent effects of dimethylarsinous acid on the cells were induction of aneuploids, tetraploids and c-mitosis. Dimethylarsinous acid can be biosynthesized from dimethylarsinate; which is mediated by the enzyme glutathione S-transferase omega-1. In humans, dimethylarsinous acid is involved in arsenate detoxification. The toxicity of dimethylarsinous acid is strongly related to the disturbance of the normal cell cycle. Dimethylarsinous acid caused mitotic arrest, since the mitotic index at toxic dose (5 μM) was 13.9%, Significantly higher than the control (2.7%). 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 is detected in the urine of individuals who ingest arsenic-polluted drinking water. Dimethylarsinous acid is a reactive organic intermediate of dimethylarsinic acid involved in toxicity. Dimethylarsinous acid significantly increased sister chromatid exchange (SCE) and chromosomal aberrations, most of which were chromatid gaps and chromatid breaks.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0091979 (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 NP0091979 (Dimethylarsinous acid)

     RDKit          3D

 11 10  0  0  0  0  0  0  0  0999 V2000
    1.7315    0.0860    0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390    0.4249   -0.6935 As  0  0  0  0  0  3  0  0  0  0  0  0
   -1.2672   -0.9354   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6066    2.0952   -0.3586 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248    0.2136    1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5686    0.6869   -0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897   -0.9859    0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4813   -1.5552   -1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1987   -0.4456    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8615   -1.6270    0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5383    2.0426   -0.0156 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 NP0091979 (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>
NP0091979

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
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3D-SDF for NP0091979 (Dimethylarsinous acid)

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PDB for NP0091979 (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 NP0091979 (Dimethylarsinous acid)
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SMILES for NP0091979 (Dimethylarsinous acid)
C[As](C)O
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INCHI for NP0091979 (Dimethylarsinous acid)
InChI=1S/C2H7AsO/c1-3(2)4/h4H,1-2H3
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View in JSmol
Synonyms
ValueSource
[As(CH3)2(OH)]ChEBI
Me2asohChEBI
DimethylarsiniteHMDB
Dimethylarsinous-acidHMDB
DmaIIIHMDB
Chemical FormulaC2H7AsO
Average Mass121.9980 Da
Monoisotopic Mass121.97129 Da
IUPAC Namedimethylarsinous acid
Traditional Namedimethylarsinous acid
CAS Registry NumberNot Available
SMILES
C[As](C)O
InChI Identifier
InChI=1S/C2H7AsO/c1-3(2)4/h4H,1-2H3
InChI KeyVDEGQTCMQUFPFH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0012216  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References