Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2009-01-30 09:50:05 UTC |
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Update Date | 2023-02-21 17:17:31 UTC |
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HMDB ID | HMDB0011625 |
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Secondary Accession Numbers | - HMDB0094715
- HMDB11625
- HMDB94715
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Metabolite Identification |
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Common Name | Dimethylarsinic acid |
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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 ). |
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Structure | InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5) |
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Synonyms | Value | Source |
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[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 |
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Chemical Formula | C2H7AsO2 |
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Average Molecular Weight | 137.9974 |
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Monoisotopic Molecular Weight | 137.966200885 |
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IUPAC Name | dimethylarsinic acid |
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Traditional Name | ansar |
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CAS Registry Number | 75-60-5 |
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SMILES | C[As](C)(O)=O |
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InChI Identifier | InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5) |
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InChI Key | OGGXGZAMXPVRFZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organometallic compounds |
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Class | Organometalloid compounds |
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Sub Class | Organoarsenic compounds |
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Direct Parent | Pentaorganoarsanes |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Dimethylarsinic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-0900000000-aacd14a23122c6fead4f | 2017-09-14 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dimethylarsinic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0596-6900000000-c094738db14b7209da38 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethylarsinic acid 10V, Positive-QTOF | splash10-000i-0900000000-277740f35cf8f3db1076 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethylarsinic acid 20V, Positive-QTOF | splash10-000i-0900000000-3ba00e60d1b6e66786aa | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethylarsinic acid 40V, Positive-QTOF | splash10-000i-0900000000-8ae8b3e2664bfccfadce | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethylarsinic acid 10V, Negative-QTOF | splash10-00di-0900000000-4605296babdf6148fcc3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethylarsinic acid 20V, Negative-QTOF | splash10-00kr-5900000000-3be49b0b6e40807a58e4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethylarsinic acid 40V, Negative-QTOF | splash10-000i-0900000000-0b14088c1c17aff4669f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethylarsinic acid 10V, Positive-QTOF | splash10-00di-0900000000-2f08307520e1e4ad4d1f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethylarsinic acid 20V, Positive-QTOF | splash10-00di-0900000000-6bc98922234d783edd28 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethylarsinic acid 40V, Positive-QTOF | splash10-0udi-0900000000-d9daf50debedfc9ab847 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethylarsinic acid 10V, Negative-QTOF | splash10-000i-0900000000-723d8270a195a697561f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethylarsinic acid 20V, Negative-QTOF | splash10-000i-0900000000-0b6b8eda42b4b4a2c55e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethylarsinic acid 40V, Negative-QTOF | splash10-0gb9-0900000000-1ab81c1f902ad9956e3b | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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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. [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 ]
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