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Showing NP-Card for Methylarsonate (NP0092002)

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Record Information
Version2.0
Created at2022-05-11 18:54:26 UTC
Updated at2022-05-11 18:54:26 UTC
NP-MRD IDNP0092002
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethylarsonate
DescriptionMethylarsonate, also known as MAA or measo(OH)2, 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. Like all arsenic compounds, it is highly toxic. Methylarsonate is a weakly acidic compound (based on its pKa). Within humans, methylarsonate participates in a number of enzymatic reactions. In particular, methylarsonate and S-adenosylhomocysteine can be biosynthesized from arsenite and S-adenosylmethionine; which is mediated by the enzyme arsenite methyltransferase. In addition, methylarsonate and glutathione can be converted into methylarsonite and oxidized glutathione; which is catalyzed by the enzyme glutathione S-transferase omega-1. These include CH3AsO3H− and CH3AsO2−3. In humans, methylarsonate is involved in arsenate detoxification. Salts of this compound, e.G. Disodium methyl arsonate, have been widely used in as a herbicides and fungicides in growing cotton and rice. This historically significant conversion is called the Meyer reaction:As(OH)3 + CH3I + NaOH → CH3AsO(OH)2 + NaI + H2OThe then novel aspect of the reaction was that alkylation occurs at As, leading to oxidation of As from III to V.The biomethylation of arsenic compounds is thought to start with the formation of methanearsonates. S-adenosylmethionine is the methyl donor. Thus, trivalent arsenic compounds are methylated to give methanearsonate. The methanearsonates are the precursors to cacodylates, again by the cycle of reduction (to methylarsonous acid) followed by a second methylation. Reaction of arsenous acid with methyl iodide gives methylarsonic acid. Methylarsonic acid is an organoarsenic compound with the formula CH3AsO3H2. It is a colorless, water-soluble solid. Near physiological pH, methanearsonic acid converts to its conjugate bases, the methylarsonates.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0092002 (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 NP0092002 (Methylarsonate)

     RDKit          3D

 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.2196   -0.5867   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5178    0.1926    0.4651 As  0  0  0  0  0  5  0  0  0  0  0  0
    0.6059    0.4479    2.0885 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8886   -0.9824    0.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7356    1.7933   -0.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8795    0.1790   -0.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7199   -1.0471    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9980   -1.3261   -0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2215   -0.7968   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523    2.1264   -0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  4  1  0
  2  5  1  0
  2  3  2  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 NP0092002 (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>
NP0092002

> <DATABASE_NAME>
NP-MRD

> <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 NP0092002 (Methylarsonate)

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PDB for NP0092002 (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 NP0092002 (Methylarsonate)
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SMILES for NP0092002 (Methylarsonate)
C[As](O)(O)=O
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INCHI for NP0092002 (Methylarsonate)
InChI=1S/CH5AsO3/c1-2(3,4)5/h1H3,(H2,3,4,5)
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View in JSmol
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 methanearsonateHMDB
Monomethylarsonic acid, ammonium, iron (3+) saltHMDB
Monomethylarsonic acid, dimercury (1+) saltHMDB
Monomethylarsonic acid, disodium saltHMDB
Monomethylarsonic acid, dipotassium saltHMDB
Monomethylarsonic acid, iron (2+) salt (3:2)HMDB
Monomethylarsonic acid, monoammonium saltHMDB
Monomethylarsonic acid, monosodium saltHMDB
Monomethylarsonic acid, zinc saltHMDB
Methylarsonous acidHMDB
Monomethylarsonic acid, iron saltHMDB
Monomethylarsonic acid, monocalcium saltHMDB
MSMAHMDB
Monomethylarsonic acid, calcium salt (2:1)HMDB
Monosodium methanearsonateHMDB
Sodium methanearsonateHMDB
Chemical FormulaCH5AsO3
Average Mass139.9702 Da
Monoisotopic Mass139.94547 Da
IUPAC Namemethylarsonic acid
Traditional Namemonomethylarsonic acid
CAS Registry NumberNot Available
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
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 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
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-1ALOGPS
logP-0.91ChemAxon
logS0.61ALOGPS
pKa (Strongest Acidic)4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity11.9 m³·mol⁻¹ChemAxon
Polarizability8.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012258  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General ReferencesNot Available