MiMeDB: Showing metabocard for Dimethylarsinate (MMDBc0053094)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:14:08 UTC

Update Date

2024-10-09 20:18:40 UTC

Metabolite ID

MMDBc0053094

Metabolite Identification

Common Name

Dimethylarsinate

Description

Dimethylarsinic acid, also known as cacodylic acid, is formally rated as possibly a carcinogenic (IARC 2B), potentially toxic compound. Derivatives of cacodylic acid, cacodylates, were frequently used as herbicides. For example, Agent Blue, one of the chemicals used during the Vietnam War, is a mixture of cacodylic acid and sodium cacodylate. Sodium cacodylate is frequently used as a buffering agent in the preparation and fixation of biological samples for transmission electron microscopy. Dimethylarsinic acid is highly toxic by ingestion, inhalation, or skin contact. Once thought to be a byproduct of inorganic arsenic detoxification, it is now believed to have serious health consequences of its own. It has been shown to be teratogenic in rodents, most often causing cleft palate but also fetal fatality at high doses. It has been shown to be genotoxic in human cells, causing apoptosis and also decreased DNA production and shorter DNA strands. While not itself a strong carcinogen, dimethylarsinic acid does promote tumours in the presence of carcinogens in organs such as the kidneys and liver (Wikipedia ).

Structure

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

Synonyms

Value	Source
[As(CH3)2O(OH)]	ChEBI
CACODYLIC ACID	ChEBI
Dimethylarsinate	ChEBI
Kakodylsaeure	ChEBI
Me2as(=o)OH	ChEBI
CACODYLate	Generator
Acid, dimethylarsinic	HMDB
Acid, cacodylic	HMDB
As,as-dimethylarsinic acid	HMDB
Dimethylarsenic acid	HMDB
Hydroxydimethylarsine oxide	HMDB
Dimethylarsinic acid	Generator

Molecular Formula

C₂H₇AsO₂

Average Mass

137.9974

Monoisotopic Mass

137.966200885

IUPAC Name

dimethylarsinic acid

Traditional Name

ansar

CAS Registry Number

Not Available

SMILES

C[As](C)(O)=O

InChI Identifier

InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)

InChI Key

OGGXGZAMXPVRFZ-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

organoarsenic compound (CHEBI:48765 )
Arsenical herbicides (C07308 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	255 g/L	ALOGPS
logP	-0.48	ALOGPS
logP	-0.33	ChemAxon
logS	0.27	ALOGPS
pKa (Strongest Acidic)	6.22	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	15.9 m³·mol⁻¹	ChemAxon
Polarizability	9.18 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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-aacd14a23122c6fead4f	2017-09-14	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	splash10-000i-0900000000-277740f35cf8f3db1076	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-3ba00e60d1b6e66786aa	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-8ae8b3e2664bfccfadce	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-4605296babdf6148fcc3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-5900000000-3be49b0b6e40807a58e4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0900000000-0b14088c1c17aff4669f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-2f08307520e1e4ad4d1f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-6bc98922234d783edd28	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0900000000-d9daf50debedfc9ab847	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-723d8270a195a697561f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-0b6b8eda42b4b4a2c55e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gb9-0900000000-1ab81c1f902ad9956e3b	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0596-6900000000-c094738db14b7209da38	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, experimental)		2014-09-20	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

Blood
Saliva
Urine

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

Human Pathways

Pathways

Name	SMPDB/PathBank
Arsenate Detoxification

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	2
Eukaryota/Fungi	Basidiomycota	3

Exposure Sources

Source Type	Activity	Data Source	Reference
Not Available	Neurodevelopment effects	U.S. Environmental Protection Agency	CompTox
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
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 Urine	Detected and Quantified	0.00328		0.00303	0.00354	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	9510859
Human Urine	Detected and Quantified	0.00328		0.00303	0.00354	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	17981925
Human Urine	Detected and Quantified	0.00391		0.00356	0.00428	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	9510859
Human Urine	Detected and Quantified	0.00391		0.00356	0.00428	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	17981925
Human Saliva	Detected and Quantified	0.005		0.0	0.018	uM	Adult (>18 years old)	Both	Normal	HMDB	17981925
Human Urine	Detected and Quantified	0.022	0.00095			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	9510859
Human Urine	Detected and Quantified	0.00328		0.00303	0.00354	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2013
Human Urine	Detected and Quantified			0.00391	0.00428	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2013
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0011625

DrugBank ID

DB02994

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cacodylic_acid

METLIN ID

Not Available

PubChem Compound

2513

PDB ID

Not Available

ChEBI ID

48765

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Yamanaka K, Mizol M, Kato K, Hasegawa A, Nakano M, Okada S: Oral administration of dimethylarsinic acid, a main metabolite of inorganic arsenic, in mice promotes skin tumorigenesis initiated by dimethylbenz(a)anthracene with or without ultraviolet B as a promoter. Biol Pharm Bull. 2001 May;24(5):510-4. doi: 10.1248/bpb.24.510. [PubMed:11379771 ]
Maki T, Hirota W, Motojima H, Hasegawa H, Rahman MA: Influence of aggregated particles on biodegradation activities for dimethylarsinic acid (DMA) in Lake Kahokugata. Chemosphere. 2011 Jun;83(11):1486-92. doi: 10.1016/j.chemosphere.2011.01.059. Epub 2011 Feb 20. [PubMed:21342701 ]

Showing metabocard for Dimethylarsinate (MMDBc0053094)

MOL for #<Metabolite:0x00007fdb71dfdaf0>

3D MOL for #<Metabolite:0x00007fdb71dfdaf0>

3D SDF for #<Metabolite:0x00007fdb71dfdaf0>

3D-SDF for #<Metabolite:0x00007fdb71dfdaf0>

PDB for #<Metabolite:0x00007fdb71dfdaf0>

3D PDB for #<Metabolite:0x00007fdb71dfdaf0>

SMILES for #<Metabolite:0x00007fdb71dfdaf0>

INCHI for #<Metabolite:0x00007fdb71dfdaf0>

Structure for #<Metabolite:0x00007fdb71dfdaf0>

3D Structure for #<Metabolite:0x00007fdb71dfdaf0>