<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">302</id>
  <title>T3D0301</title>
  <common-name>Arsenobetaine</common-name>
  <description>Arsenobetaine is found in crustaceans. Arsenobetaine is found in algae, lobsters, sharks, etc. Arsenobetaine is an organoarsenic compound that is the main source of arsenic found in fish. It is the arsenic analogue of trimethylglycine, commonly known as betaine. The biochemistry and its biosynthesis are similar to the biosynthesis of choline and betaine. The; Besides several other arsenic compounds, such as dimethylarsine and trimethylarsine, arsenobetaine is a common substance in the marine biological systems for arsenic detoxification.</description>
  <cas>64436-13-1</cas>
  <pubchem-id>47364</pubchem-id>
  <chemical-formula>C5H11AsO2</chemical-formula>
  <weight>177.997500</weight>
  <appearance>No data.</appearance>
  <melting-point>204 - 210°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral (L2) ; inhalation (L2);  dermal (L2)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Arsenic and its metabolites disrupt ATP production through several mechanisms. At the level of the citric acid cycle, arsenic inhibits pyruvate dehydrogenase and by competing with phosphate it uncouples oxidative phosphorylation, thus inhibiting energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is also increased, which might form reactive oxygen species and oxidative stress. Arsenic's carginogenicity is influenced by the arsenical binding of tubulin, which results in aneuploidy, polyploidy and mitotic arrests. The binding of other arsenic protein targets may also cause altered DNA repair enzyme activity, altered DNA methylation patterns and cell proliferation. (T1, A17)</mechanism-of-toxicity>
  <metabolism>Arsenic is absorbed mainly by inhalation or ingestion, as to a lesser extent, dermal exposure. It is then distributed throughout the body, where it is reduced into arsenite if necessary, then methylated into monomethylarsenic (MMA) and dimethylarsenic acid (DMA) by arsenite methyltransferase. Arsenic and its metabolites are primarily excreted in the urine. Arsenic is known to induce the metal-binding protein metallothionein, which decreases the toxic effects of arsenic and other metals by binding them and making them biologically inactive, as well as acting as an antioxidant. (L20)</metabolism>
  <toxicity>LD50:  &gt;4260 mg/kg (Oral, Mouse) (A577)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use-source>Arsenobetaine is found in marine biological systems. (L387)</use-source>
  <min-risk-level>Acute Oral: 0.005 mg/kg/day (L134) 
Chronic Oral: 0.0003 mg/kg/day (L134) 
Chronic Inhalation: 0.01 mg/m3 (L134)</min-risk-level>
  <health-effects>Arsenic poisoning can lead to death from multi-system organ failure, probably from necrotic cell death, not apoptosis. Arsenic is also a known carcinogen, esepcially in skin, liver, bladder and lung cancers. (T1, L20)</health-effects>
  <symptoms>Exposure to lower levels of arsenic can cause nausea and vomiting, decreased production of red and white blood cells, abnormal heart rhythm, damage to blood vessels, and a sensation of burn (T1).</symptoms>
  <treatment>Arsenic poisoning can be treated by chelation therapy, using chelating agents such as dimercaprol, EDTA or DMSA. Charcoal tablets may also be used for less severe cases. In addition, maintaining a diet high in sulfur helps eliminate arsenic from the body. (L20)</treatment>
  <created-at type="dateTime">2009-03-06T18:58:28Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:21:30Z</updated-at>
  <interacting-proteins>Metallothionein-2 (P02795) Metallothionein-1G (P13640) Metallothionein-1H (P80294) Metallothionein-3 (P25713) Metallothionein-1F (P04733) Metallothionein-1E (P04732) Metallothionein-1X (P80297) Metallothionein-1A (P04731) Metallothionein-1B (P07438) Metallothionein-1M (Q8N339) Metallothionein-4 (P47944) Metallothionein-1L (Q93083) Arsenite methyltransferase (Q9HBK9) (L92)</interacting-proteins>
  <wikipedia>http://en.wikipedia.org/wiki/Arsenobetaine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C19331</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id>C038992</ctd-id>
  <stitch-id>Arsenobetaine</stitch-id>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins>Arsenite methyltransferase (Q9HBK9) 
(L92)</metabolizing-proteins>
  <transporting-proteins>Metallothionein-2 (P02795) 
Metallothionein-1G (P13640) 
Metallothionein-1H (P80294) 
Metallothionein-3 (P25713) 
Metallothionein-1F (P04733) 
Metallothionein-1E (P04732) 
Metallothionein-1X (P80297) 
Metallothionein-1A (P04731) 
Metallothionein-1B (P07438) 
Metallothionein-1M (Q8N339) 
Metallothionein-4 (P47944) 
Metallothionein-1L (Q93083) 
(L92)</transporting-proteins>
  <moldb-smiles>C[As+](C)(C)CC([O-])=O</moldb-smiles>
  <moldb-formula>C5H11AsO2</moldb-formula>
  <moldb-inchi>InChI=1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3</moldb-inchi>
  <moldb-inchikey>InChIKey=SPTHHTGLGVZZRH-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">178.0612</moldb-average-mass>
  <moldb-mono-mass type="decimal">177.997501013</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB33206</hmdb-id>
  <chembl-id>CHEMBL2448348</chembl-id>
  <chemspider-id>43109</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference nil="true"/>
  <structure-image-caption nil="true"/>
</compound>
