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Showing metabocard for Methylarsonate (HMDB0012258)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:53 UTC
Update Date2023-02-21 17:17:46 UTC
HMDB IDHMDB0012258
Secondary Accession Numbers
  • HMDB0011682
  • HMDB11682
  • HMDB12258
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
Data?1676999866
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012258 (Methylarsonate)

  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 HMDB0012258 (Methylarsonate)

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 HMDB0012258 (Methylarsonate)

  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>
HMDB0012258

> <DATABASE_NAME>
hmdb

> <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 HMDB0012258 (Methylarsonate)

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 HMDB0012258 (Methylarsonate)

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 HMDB0012258 (Methylarsonate)

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 HMDB0012258 (Methylarsonate)

C[As](O)(O)=O
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INCHI for HMDB0012258 (Methylarsonate)

InChI=1S/CH5AsO3/c1-2(3,4)5/h1H3,(H2,3,4,5)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaCH5AsO3
Average Molecular Weight139.9702
Monoisotopic Molecular Weight139.945465443
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
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
Physiological effectNot Available
Disposition
Biological locationSource
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+118.232859911
AllCCS[M+H-H2O]+114.332859911
AllCCS[M+NH4]+121.932859911
AllCCS[M+Na]+122.932859911
AllCCS[M-H]-154.032859911
AllCCS[M+Na-2H]-159.432859911
AllCCS[M+HCOO]-165.432859911

Predicted Kovats Retention Indices

Not Available
Spectra
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 IDFDB028897
KNApSAcK IDNot Available
Chemspider ID8604
KEGG Compound IDC07294
BioCyc IDMETHYLARSONATE
BiGG IDNot Available
Wikipedia LinkMethylarsonic acid
METLIN IDNot Available
PubChem Compound8948
PDB IDNot Available
ChEBI ID29852
Food Biomarker OntologyNot Available
VMH IDM02474
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Arsenite methyltransferase
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 + Arsenite → S-Adenosylhomocysteine + Methylarsonatedetails
Enzyme Details
2. Glutathione S-transferase omega-1
General function:
Involved in glutathione transferase activity
Specific function:
Exhibits glutathione-dependent thiol transferase and dehydroascorbate reductase activities. Has S-(phenacyl)glutathione reductase activity. Has also glutathione S-transferase activity. Participates in the biotransformation of inorganic arsenic and reduces monomethylarsonic acid (MMA) and dimethylarsonic acid.
Gene Name:
GSTO1
Uniprot ID:
P78417
Molecular weight:
27565.6
Reactions
Methylarsonate + Glutathione → Methylarsonite + Oxidized glutathione + Waterdetails
Enzyme Details
3. Glutathione S-transferase omega-2
General function:
Involved in glutathione transferase activity
Specific function:
Exhibits glutathione-dependent thiol transferase activity. Has high dehydroascorbate reductase activity and may contribute to the recycling of ascorbic acid. Participates in the biotransformation of inorganic arsenic and reduces monomethylarsonic acid (MMA).
Gene Name:
GSTO2
Uniprot ID:
Q9H4Y5
Molecular weight:
24399.09
Reactions
Methylarsonate + Glutathione → Methylarsonite + Oxidized glutathione + Waterdetails