Showing metabocard for Dimethylarsinate (MMDBc0053094)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-05-16 21:14:08 UTC
Update Date2022-09-01 02:19:39 UTC
Metabolite IDMMDBc0053094
Metabolite Identification
Common NameDimethylarsinate
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000560be1f76050>


  Mrv1652305201900232D          

  5  4  0  0  0  0            999 V2000
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 As  0  0  0  0  0  5  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  2  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000560be1f76050>

HMDB0011625
     RDKit          3D
Dimethylarsinic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
    1.6793   -0.2473   -0.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529    0.5601    0.4105 As  0  0  0  0  0  5  0  0  0  0  0  0
   -1.3613   -0.8229    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3057    0.8288    1.9934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4901    2.0322   -0.5054 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7142   -0.1314   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5415    0.2239    0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087   -1.3285   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227   -1.7639    0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329   -0.4747    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097   -0.9027   -0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858    2.0264   -0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  2  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
  5 12  1  0
M  END
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3D SDF for #<Metabolite:0x0000560be1f76050>


  Mrv1652305201900232D          

  5  4  0  0  0  0            999 V2000
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 As  0  0  0  0  0  5  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  2  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0053094

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)

> <INCHI_KEY>
OGGXGZAMXPVRFZ-UHFFFAOYSA-N

> <FORMULA>
C2H7AsO2

> <MOLECULAR_WEIGHT>
137.9974

> <EXACT_MASS>
137.966200885

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
9.178944868338649

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
dimethylarsinic acid

> <ALOGPS_LOGP>
-0.48

> <JCHEM_LOGP>
-0.32920000000000016

> <ALOGPS_LOGS>
0.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.222333786503422

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
15.898900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.55e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ansar

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x0000560be1f76050>

HMDB0011625
     RDKit          3D
Dimethylarsinic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
    1.6793   -0.2473   -0.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529    0.5601    0.4105 As  0  0  0  0  0  5  0  0  0  0  0  0
   -1.3613   -0.8229    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3057    0.8288    1.9934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4901    2.0322   -0.5054 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7142   -0.1314   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5415    0.2239    0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087   -1.3285   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227   -1.7639    0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329   -0.4747    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097   -0.9027   -0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858    2.0264   -0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  2  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
  5 12  1  0
M  END
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PDB for #<Metabolite:0x0000560be1f76050>

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    2 As   UNK     0       1.540   0.000   0.000  0.00  0.00          As+0
HETATM    3  C   UNK     0       1.540   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.080   0.000   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for #<Metabolite:0x0000560be1f76050>

COMPND    HMDB0011625
HETATM    1  C1  UNL     1       1.679  -0.247  -0.379  1.00  0.00           C  
HETATM    2 AS1  UNL     1       0.053   0.560   0.410  1.00  0.00          AS  
HETATM    3  C2  UNL     1      -1.361  -0.823   0.184  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.306   0.829   1.993  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.490   2.032  -0.505  1.00  0.00           O  
HETATM    6  H1  UNL     1       1.714  -0.131  -1.466  1.00  0.00           H  
HETATM    7  H2  UNL     1       2.542   0.224   0.141  1.00  0.00           H  
HETATM    8  H3  UNL     1       1.709  -1.328  -0.054  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.923  -1.764   0.517  1.00  0.00           H  
HETATM   10  H5  UNL     1      -2.233  -0.475   0.732  1.00  0.00           H  
HETATM   11  H6  UNL     1      -1.510  -0.903  -0.916  1.00  0.00           H  
HETATM   12  H7  UNL     1      -1.486   2.026  -0.658  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    4    4    5
CONECT    3    9   10   11
CONECT    5   12
END
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SMILES for #<Metabolite:0x0000560be1f76050>

C[As](C)(O)=O
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INCHI for #<Metabolite:0x0000560be1f76050>

InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)
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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
Molecular FormulaC2H7AsO2
Average Mass137.9974
Monoisotopic Mass137.966200885
IUPAC Namedimethylarsinic acid
Traditional Nameansar
CAS Registry NumberNot Available
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