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Record Information
Version1.0
Creation Date2009-03-06 18:58:28 UTC
Update Date2016-11-09 01:08:12 UTC
Accession NumberCHEM000252
Identification
Common NameArsenobetaine
ClassSmall Molecule
DescriptionArsenobetaine 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.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Arsenic Compound
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Organometallic
Chemical Structure
Thumb
Synonyms
ValueSource
(Carboxymethyl)trimethylarsonium hydroxide inner saltHMDB
(Carboxymethyl)trimethylarsonium hydroxide inner salt, 9ciHMDB
2-(Trimethylarsonio)acetateHMDB
Arsenobetaine monohydrateHMDB
Arsonium, (carboxymethyl)trimethyl-, hydroxide, inner saltHMDB
Chemical FormulaC5H11AsO2
Average Molecular Mass178.061 g/mol
Monoisotopic Mass177.998 g/mol
CAS Registry Number64436-13-1
IUPAC Name2-(trimethylarsaniumyl)acetate
Traditional Namearsenobetaine
SMILESC[As+](C)(C)CC([O-])=O
InChI IdentifierInChI=1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
InChI KeySPTHHTGLGVZZRH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetraorganoarsonium salts. These are organoarsenic compounds, where the arsenic atom is tetrasubstituted by organic groups. They have the general structure R4[As+]X-, X=any atom but H.
KingdomOrganic compounds
Super ClassOrganometallic compounds
ClassOrganometalloid compounds
Sub ClassOrganoarsenic compounds
Direct ParentTetraorganoarsonium salts
Alternative Parents
Substituents
  • Tetraorganoarsonium salt
  • Carboxylic acid salt
  • Oxygen-containing organoarsenic compound
  • Organic metalloid salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceNo data.
Experimental Properties
PropertyValue
Melting Point204 - 210°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility6 g/LALOGPS
logP1.84ALOGPS
logP0.94ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.27 m³·mol⁻¹ChemAxon
Polarizability13.9 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0400-2900000000-87ae859df28e772e20deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-db2b71a9b1e552a5dd68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-7451c19f2ce0c2ad26feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0550-3900000000-13badada4bf33596b142View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-04587c1087dd728fb563View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3900000000-49065dd3149cd41b348fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5900000000-d2fc0322a2d3012fa8deView in MoNA
Toxicity Profile
Route of ExposureOral (7) ; inhalation (7); dermal (7)
Mechanism of ToxicityArsenic 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. (3, 1)
MetabolismArsenic 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. (8)
Toxicity ValuesLD50: >4260 mg/kg (Oral, Mouse) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (11)
Uses/SourcesArsenobetaine is found in marine biological systems. (12)
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (10) Chronic Oral: 0.0003 mg/kg/day (10) Chronic Inhalation: 0.01 mg/m3 (10)
Health EffectsArsenic 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. (3, 8)
SymptomsExposure 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 (3).
TreatmentArsenic 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. (8)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0033206
FooDB IDFDB011219
Phenol Explorer IDNot Available
KNApSAcK IDC00033652
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkArsenobetaine
Chemspider ID43109
ChEBI IDNot Available
PubChem Compound ID47364
Kegg Compound IDC19331
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.