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Showing metabocard for Methylarsonite (HMDB0012259)

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enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:54 UTC
Update Date2023-02-21 17:17:47 UTC
HMDB IDHMDB0012259
Secondary Accession Numbers
  • HMDB12259
Metabolite Identification
Common NameMethylarsonite
DescriptionMethylarsonite, also known as meas(OH)2 or mma(iii), belongs to the class of organic compounds known as trivalent organic arsenic compounds. These are organoarsenic compounds in which a carbon is linked to a trivalent arsenic atom. In humans, methylarsonite is involved in the arsenate detoxification pathway. Methylarsonite has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make methylarsonite a potential biomarker for the consumption of these foods. Methylarsonite is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Methylarsonite.
Structure
Data?1676999867
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012259 (Methylarsonite)


  Mrv0541 02241203532D          

  4  3  0  0  0  0            999 V2000
   11.6147  -13.4188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4397  -13.4188    0.0000 As  0  0  0  0  0  0  0  0  0  0  0  0
   12.8523  -14.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8523  -12.7043    0.0000 C   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
M  END
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3D MOL for HMDB0012259 (Methylarsonite)

HMDB0012259
     RDKit          3D
Methylarsonite
  9  8  0  0  0  0  0  0  0  0999 V2000
    1.2618   -0.1300    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373    0.3889    0.8784 As  0  0  0  0  0  3  0  0  0  0  0  0
   -1.2633    1.6367   -0.2173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4967   -1.1362    0.9251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    0.4171    0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4208   -1.2300    0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2197    0.1130   -1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0366    1.3381   -1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7556   -1.3974    0.0117 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
  4  9  1  0
M  END
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3D SDF for HMDB0012259 (Methylarsonite)


  Mrv0541 02241203532D          

  4  3  0  0  0  0            999 V2000
   11.6147  -13.4188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4397  -13.4188    0.0000 As  0  0  0  0  0  0  0  0  0  0  0  0
   12.8523  -14.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8523  -12.7043    0.0000 C   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
M  END
> <DATABASE_ID>
HMDB0012259

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/CH5AsO2/c1-2(3)4/h3-4H,1H3

> <INCHI_KEY>
OXBIRPQQKCQWGV-UHFFFAOYSA-N

> <FORMULA>
CH5AsO2

> <MOLECULAR_WEIGHT>
123.9708

> <EXACT_MASS>
123.950550821

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
7.3403560539950945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methylarsonous acid

> <ALOGPS_LOGP>
-0.90

> <JCHEM_LOGP>
-0.9956999999999999

> <ALOGPS_LOGS>
0.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.750355548875898

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.648861683976767

> <JCHEM_PKA_STRONGEST_BASIC>
-5.445117379325137

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
11.0749

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.08e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylarsonous acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0012259 (Methylarsonite)

HMDB0012259
     RDKit          3D
Methylarsonite
  9  8  0  0  0  0  0  0  0  0999 V2000
    1.2618   -0.1300    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373    0.3889    0.8784 As  0  0  0  0  0  3  0  0  0  0  0  0
   -1.2633    1.6367   -0.2173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4967   -1.1362    0.9251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    0.4171    0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4208   -1.2300    0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2197    0.1130   -1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0366    1.3381   -1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7556   -1.3974    0.0117 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
  4  9  1  0
M  END
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PDB for HMDB0012259 (Methylarsonite)

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      21.681 -25.048   0.000  0.00  0.00           O+0
HETATM    2 As   UNK     0      23.221 -25.048   0.000  0.00  0.00          As+0
HETATM    3  O   UNK     0      23.991 -26.382   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      23.991 -23.715   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for HMDB0012259 (Methylarsonite)

COMPND    HMDB0012259
HETATM    1  C1  UNL     1       1.262  -0.130   0.030  1.00  0.00           C  
HETATM    2 AS1  UNL     1      -0.437   0.389   0.878  1.00  0.00          AS  
HETATM    3  O1  UNL     1      -1.263   1.637  -0.217  1.00  0.00           O  
HETATM    4  O2  UNL     1      -1.497  -1.136   0.925  1.00  0.00           O  
HETATM    5  H1  UNL     1       2.087   0.417   0.492  1.00  0.00           H  
HETATM    6  H2  UNL     1       1.421  -1.230   0.087  1.00  0.00           H  
HETATM    7  H3  UNL     1       1.220   0.113  -1.054  1.00  0.00           H  
HETATM    8  H4  UNL     1      -1.037   1.338  -1.153  1.00  0.00           H  
HETATM    9  H5  UNL     1      -1.756  -1.397   0.012  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    4
CONECT    3    8
CONECT    4    9
END
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SMILES for HMDB0012259 (Methylarsonite)

C[As](O)O
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INCHI for HMDB0012259 (Methylarsonite)

InChI=1S/CH5AsO2/c1-2(3)4/h3-4H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
MeAs(OH)2ChEBI
Methanearsonous acidChEBI
Mma(III)ChEBI
MMAIIIChEBI
Monomethylarsenous acidChEBI
Monomethylarsonous acidChEBI
Methyl arsonous acidHMDB
Methylarsonous acidHMDB
MethylarsoniteChEBI
Chemical FormulaCH5AsO2
Average Molecular Weight123.9708
Monoisotopic Molecular Weight123.950550821
IUPAC Namemethylarsonous acid
Traditional Namemethylarsonous acid
CAS Registry Number25400-23-1
SMILES
C[As](O)O
InChI Identifier
InChI=1S/CH5AsO2/c1-2(3)4/h3-4H,1H3
InChI KeyOXBIRPQQKCQWGV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trivalent organic arsenic compounds. These are organoarsenic compounds in which a carbon is linked to a trivalent arsenic atom.
KingdomOrganic compounds
Super ClassOrganometallic compounds
ClassOrganometalloid compounds
Sub ClassOrganoarsenic compounds
Direct ParentTrivalent organic arsenic compounds
Alternative Parents
Substituents
  • Trivalent organic arsenic compound
  • Organoarsonous acid
  • Oxygen-containing organoarsenic compound
  • Organic metalloid salt
  • Organic oxygen compound
  • Organopnictogen compound
  • 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
PropertyValueSource
Water Solubility708 g/LALOGPS
logP-0.9ALOGPS
logP-1ChemAxon
logS0.76ALOGPS
pKa (Strongest Acidic)8.65ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity11.07 m³·mol⁻¹ChemAxon
Polarizability7.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+128.432859911
AllCCS[M+H-H2O]+124.432859911
AllCCS[M+NH4]+132.232859911
AllCCS[M+Na]+133.332859911
AllCCS[M-H]-168.832859911
AllCCS[M+Na-2H]-175.532859911
AllCCS[M+HCOO]-182.832859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methylarsonite GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0900000000-918a2f74d7a06f030bdb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylarsonite GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonite 10V, Positive-QTOFsplash10-00di-0900000000-3c1ffe084e9cde17253c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonite 20V, Positive-QTOFsplash10-00di-0900000000-f5c1555d242b5cfb66df2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonite 40V, Positive-QTOFsplash10-00di-1900000000-9ca9523309b2398cace92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonite 10V, Negative-QTOFsplash10-05fr-0900000000-7d39868bc634bbb4eed92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonite 20V, Negative-QTOFsplash10-00di-3900000000-4a208e1f8bbc2408905a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonite 40V, Negative-QTOFsplash10-00di-0900000000-3436bb44a28cdbfdb0732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonite 10V, Positive-QTOFsplash10-0a4i-0900000000-04ff3b77ed27d61b3ee02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonite 20V, Positive-QTOFsplash10-05fr-0900000000-09411558d1a28092c8ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonite 40V, Positive-QTOFsplash10-0a4i-0900000000-b738fe015e68765936632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonite 10V, Negative-QTOFsplash10-00di-0900000000-b9386edb712997f0fe382021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonite 20V, Negative-QTOFsplash10-00di-0900000000-ad763b0546afa2eb540e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylarsonite 40V, Negative-QTOFsplash10-00di-0900000000-57271e409d3d626e73292021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
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 IDFDB028898
KNApSAcK IDNot Available
Chemspider ID141846
KEGG Compound IDC07295
BioCyc IDMETHYLARSONITE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound161491
PDB IDNot Available
ChEBI ID17826
Food Biomarker OntologyNot Available
VMH IDNot Available
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 + Methylarsonite → S-Adenosylhomocysteine + Dimethylarsinic aciddetails
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