MiMeDB: Showing metabocard for Methylarsonate (MMDBc0048394)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:58:51 UTC

Update Date

2025-01-15 23:20:20 UTC

Metabolite ID

MMDBc0048394

Metabolite Identification

Common Name

Methylarsonate

Description

Methylarsonate 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
MAA	ChEBI
MeAsO(OH)2	ChEBI
Methanearsonic acid	ChEBI
Monomethylarsonic acid	ChEBI
Methylarsonic acid	Kegg
Methanearsonate	Generator
Monomethylarsonate	Generator
Dsma (jmaf)	HMDB
Kyselina methylarsonova	HMDB
Methyl arsonic acid	HMDB
Methylarsenic acid	HMDB
Methylarsinic acid	HMDB
Monomethylarsinic acid	HMDB
Disodium methanearsonate	MeSH, HMDB
Monomethylarsonic acid, ammonium, iron (3+) salt	MeSH, HMDB
Monomethylarsonic acid, dimercury (1+) salt	MeSH, HMDB
Monomethylarsonic acid, disodium salt	MeSH, HMDB
Monomethylarsonic acid, dipotassium salt	MeSH, HMDB
Monomethylarsonic acid, iron (2+) salt (3:2)	MeSH, HMDB
Monomethylarsonic acid, monoammonium salt	MeSH, HMDB
Monomethylarsonic acid, monosodium salt	MeSH, HMDB
Monomethylarsonic acid, zinc salt	MeSH, HMDB
Methylarsonous acid	MeSH, HMDB
Monomethylarsonic acid, iron salt	MeSH, HMDB
Monomethylarsonic acid, monocalcium salt	MeSH, HMDB
MSMA	MeSH, HMDB
Monomethylarsonic acid, calcium salt (2:1)	MeSH, HMDB
Monosodium methanearsonate	MeSH, HMDB
Sodium methanearsonate	MeSH, HMDB

Molecular Formula

CH₅AsO₃

Average Mass

139.9702

Monoisotopic Mass

139.945465443

IUPAC Name

methylarsonic acid

Traditional Name

monomethylarsonic acid

CAS Registry Number

124-58-3

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

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.

Kingdom

Organic compounds

Super Class

Organometallic compounds

Class

Organometalloid compounds

Sub Class

Organoarsenic compounds

Direct Parent

Pentaorganoarsanes

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 Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:29852 )
organoarsonic acid (CHEBI:29852 )
arsonic acids (CHEBI:29852 )
Arsenical herbicides (C07294 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	569 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.91	ChemAxon
logS	0.61	ALOGPS
pKa (Strongest Acidic)	4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	11.9 m³·mol⁻¹	ChemAxon
Polarizability	8.14 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0900000000-da4d5da1a88bf0f506f4	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-f551e617364ce9ae8012	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-2b6d3fe988a733ee8b82	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0900000000-5b1e291e8a048e93b1bb	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dr-0900000000-faba21d1399d2be5f4cc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-3900000000-c63ab6bc2dbdb52cf07f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0079-0900000000-af38e8044b6fdf1533a7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-0900000000-5b44146ed9e26a03f3f0	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-0900000000-f2dd94a490343ba79810	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0900000000-59b264953374dcd1e76a	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-387eed30d629c4fb0569	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-59b86cdf1af4cd9c1048	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-0900000000-2b854fae760c89475df5	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192075	Arsenite methyltransferase	Unknown	Q9HBK9	Homo sapiens
MMDBp0192442	Glutathione S-transferase omega-1	Enzyme	P78417	Homo sapiens
MMDBp0192451	Glutathione S-transferase omega-2	Enzyme	Q9H4Y5	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
Arsenate Detoxification

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0010692	S-Adenosylmethionine	S-Adenosylhomocysteine	arsenite methyltransferase		VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Firmicutes	1	Human
Archaea/Archaea	Euryarchaeota	2
Bacteria	Proteobacteria	1
Bacteria/Eubacteria	Proteobacteria	1

Exposure Sources

Other Exposures

Source Type	Activity	Data Source	Reference
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Water	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0012258

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028897

KNApSAcK ID

Not Available

Chemspider ID

8604

KEGG Compound ID

C07294

BioCyc ID

METHYLARSONATE

BiGG ID

Not Available

Wikipedia Link

Methylarsonic acid

METLIN ID

Not Available

PubChem Compound

8948

PDB ID

Not Available

ChEBI ID

29852

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Methylarsonate (MMDBc0048394)

MOL for #<Metabolite:0x00007fc9e58fc008>

3D MOL for #<Metabolite:0x00007fc9e58fc008>

3D SDF for #<Metabolite:0x00007fc9e58fc008>

3D-SDF for #<Metabolite:0x00007fc9e58fc008>

PDB for #<Metabolite:0x00007fc9e58fc008>

3D PDB for #<Metabolite:0x00007fc9e58fc008>

SMILES for #<Metabolite:0x00007fc9e58fc008>

INCHI for #<Metabolite:0x00007fc9e58fc008>

Structure for #<Metabolite:0x00007fc9e58fc008>

3D Structure for #<Metabolite:0x00007fc9e58fc008>