Showing metabocard for Methylarsonate (MMDBc0048394)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 21:58:51 UTC
Update Date2025-01-15 23:20:20 UTC
Metabolite IDMMDBc0048394
Metabolite Identification
Common NameMethylarsonate
DescriptionMethylarsonate is used as a contact herbicide in either the monosodium or disodium salt form. It goes by the trade names Weed-E-Rad, Ansar 170 H.C., Ansar 529 H.C., DiTac and others. Methylarsonate is considered only slightly toxic, having an oral LD50 of 2200 mg/Kg for rats. The inhalation risk is greater with LD50 Rats >20 mg. Long term studies with people exposed to organoarsenicals has shown an increased risk of skin cancer (Spiewak, 2001), lung cancer and some liver cancers, although some recent studies have shown some arsenic containing compounds (specifically Arsine trioxide) may have anticarcinogenic properties (Wang, 2001). In mammals, Methylarsonate is also an intermediate in the detoxification of inorganic arsenic. In the arsenate detoxification I pathway, arsenite reacts with S-adenosyl-L-methionine to produce methylarsonate and S-adenosyl-L-homocysteine. Arsenite methyltransferase catalyzes this reaction. Methylarsonate then reacts with 2 glutathione molecules to produce glutathione disulfide and methylarsonite. This reaction is catalyzed by methylarsonate reductase. Methylarsonate is an organic arsenic compound with adverse effects similar to those of arsenic trioxide. Arsenic is found in the environment primarily as arsenate and arsenite species. Arsenate is reduced to arsenite by arsenate reductase and can be subsequently methylated to Methylarsonate. This is then reduced and methylated to Dimethylarsinate, which can excreted and is considerably less toxic to the organism than any of the previous intermediate compounds. Methylarsonate was formerly included in some vitamin and mineral preparations. It was once used to treat tuberculosis, chorea, and other affections in which the cacodylates were used.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f921d410440>


  Mrv0541 02241203532D          

  5  4  0  0  0  0            999 V2000
   11.8209  -13.4187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6459  -13.4187    0.0000 As  0  0  0  0  0  0  0  0  0  0  0  0
   12.6459  -14.2437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6459  -12.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4709  -13.4187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  2  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f921d410440>

HMDB0012258
     RDKit          3D
Methylarsonate
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.3419   -0.1629   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4393    0.0843    0.5758 As  0  0  0  0  0  5  0  0  0  0  0  0
    0.2940    0.2532    2.2132 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615   -1.4005    0.2818 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1906    1.6063   -0.0773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631    0.6984    0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383   -1.0734    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302   -0.1848   -1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885   -1.4917   -0.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1997    1.6710   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  4  9  1  0
  5 10  1  0
M  END
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3D SDF for #<Metabolite:0x00007f921d410440>


  Mrv0541 02241203532D          

  5  4  0  0  0  0            999 V2000
   11.8209  -13.4187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6459  -13.4187    0.0000 As  0  0  0  0  0  0  0  0  0  0  0  0
   12.6459  -14.2437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6459  -12.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4709  -13.4187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  2  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0048394

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/CH5AsO3/c1-2(3,4)5/h1H3,(H2,3,4,5)

> <INCHI_KEY>
QYPPRTNMGCREIM-UHFFFAOYSA-N

> <FORMULA>
CH5AsO3

> <MOLECULAR_WEIGHT>
139.9702

> <EXACT_MASS>
139.945465443

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
8.140744707305412

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methylarsonic acid

> <ALOGPS_LOGP>
-1.05

> <JCHEM_LOGP>
-0.9120999999999997

> <ALOGPS_LOGS>
0.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.5814908650188

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.196018882390285

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
11.8974

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.69e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
monomethylarsonic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f921d410440>

HMDB0012258
     RDKit          3D
Methylarsonate
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.3419   -0.1629   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4393    0.0843    0.5758 As  0  0  0  0  0  5  0  0  0  0  0  0
    0.2940    0.2532    2.2132 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615   -1.4005    0.2818 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1906    1.6063   -0.0773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631    0.6984    0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383   -1.0734    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302   -0.1848   -1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885   -1.4917   -0.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1997    1.6710   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  4  9  1  0
  5 10  1  0
M  END
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PDB for #<Metabolite:0x00007f921d410440>

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  O   UNK     0      22.066 -25.048   0.000  0.00  0.00           O+0
HETATM    2 As   UNK     0      23.606 -25.048   0.000  0.00  0.00          As+0
HETATM    3  O   UNK     0      23.606 -26.588   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      23.606 -23.508   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      25.146 -25.048   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:0x00007f921d410440>

COMPND    HMDB0012258
HETATM    1  C1  UNL     1      -1.342  -0.163  -0.230  1.00  0.00           C  
HETATM    2 AS1  UNL     1       0.439   0.084   0.576  1.00  0.00          AS  
HETATM    3  O1  UNL     1       0.294   0.253   2.213  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.461  -1.400   0.282  1.00  0.00           O  
HETATM    5  O3  UNL     1       1.191   1.606  -0.077  1.00  0.00           O  
HETATM    6  H1  UNL     1      -1.963   0.698   0.109  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.838  -1.073   0.137  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.230  -0.185  -1.325  1.00  0.00           H  
HETATM    9  H4  UNL     1       1.789  -1.492  -0.629  1.00  0.00           H  
HETATM   10  H5  UNL     1       1.200   1.671  -1.056  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    3    4    5
CONECT    4    9
CONECT    5   10
END
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SMILES for #<Metabolite:0x00007f921d410440>

C[As](O)(O)=O
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INCHI for #<Metabolite:0x00007f921d410440>

InChI=1S/CH5AsO3/c1-2(3,4)5/h1H3,(H2,3,4,5)
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Synonyms
ValueSource
MAAChEBI
MeAsO(OH)2ChEBI
Methanearsonic acidChEBI
Monomethylarsonic acidChEBI
Methylarsonic acidKegg
MethanearsonateGenerator
MonomethylarsonateGenerator
Dsma (jmaf)HMDB
Kyselina methylarsonovaHMDB
Methyl arsonic acidHMDB
Methylarsenic acidHMDB
Methylarsinic acidHMDB
Monomethylarsinic acidHMDB
Disodium methanearsonateMeSH, HMDB
Monomethylarsonic acid, ammonium, iron (3+) saltMeSH, HMDB
Monomethylarsonic acid, dimercury (1+) saltMeSH, HMDB
Monomethylarsonic acid, disodium saltMeSH, HMDB
Monomethylarsonic acid, dipotassium saltMeSH, HMDB
Monomethylarsonic acid, iron (2+) salt (3:2)MeSH, HMDB
Monomethylarsonic acid, monoammonium saltMeSH, HMDB
Monomethylarsonic acid, monosodium saltMeSH, HMDB
Monomethylarsonic acid, zinc saltMeSH, HMDB
Methylarsonous acidMeSH, HMDB
Monomethylarsonic acid, iron saltMeSH, HMDB
Monomethylarsonic acid, monocalcium saltMeSH, HMDB
MSMAMeSH, HMDB
Monomethylarsonic acid, calcium salt (2:1)MeSH, HMDB
Monosodium methanearsonateMeSH, HMDB
Sodium methanearsonateMeSH, HMDB
Molecular FormulaCH5AsO3
Average Mass139.9702
Monoisotopic Mass139.945465443
IUPAC Namemethylarsonic acid
Traditional Namemonomethylarsonic acid
CAS Registry Number124-58-3
SMILES
C[As](O)(O)=O
InChI Identifier
InChI=1S/CH5AsO3/c1-2(3,4)5/h1H3,(H2,3,4,5)
InChI KeyQYPPRTNMGCREIM-UHFFFAOYSA-N