Triphenylarsine (CHEM001134)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (69)XML
Record Information
Version1.0
Creation Date2009-06-19 21:58:35 UTC
Update Date2026-08-19 23:08:23 UTC
Accession NumberCHEM001134
Identification
Common NameTriphenylarsine
ClassSmall Molecule
DescriptionTriphenylarsine (C18H15As) is an organic compound with an average molecular weight of 306.23 g/mol. It exists as a solid at room temperature and is exogenous in origin. Triphenylarsine belongs to the benzene and substituted derivatives, a class of benzenoids within the organic compounds. It is used as a ligand and a reagent in coordination chemistry and organic synthesis. This compound has been recorded as being found in or released from two sources: food, food processing and cookware specifically regarding fermentation processes for beer, and electrical and electronic equipment, specifically conductors or conductive bodies characterized by the conductive materials. The compound interacts with 32 recorded protein targets. It binds to the estrogen receptor (ESR1), the glucocorticoid receptor (NR3C1), haptoglobin, and hemoglobin subunits alpha (HBA1) and beta (HBB). It also binds to various actin proteins, including alpha skeletal muscle (ACTA1), aortic smooth muscle (ACTA2), cytoplasmic 1 (ACTB), and cytoplasmic 2 (ACTG1). Arsenic binding of XPA is believed to induce carcinogenesis by affecting DNA repair. Furthermore, it binds glutathione reductase, mitochondrial (GSR), resulting in the inhibition of essential biochemical reactions, alteration of cellular redox status, and eventual cytotoxicity. Arsenic disrupts ATP production by inhibiting pyruvate dehydrogenase—specifically the PDHB subunit and the PDHA1 and PDHA2 E1 component subunit alpha, as well as the DLAT dihydrolipoyllysine-residue acetyltransferase component of the mitochondrial pyruvate dehydrogenase complex. By competing with phosphate, it uncouples oxidative phosphorylation, inhibiting mitochondrial respiration, ATP synthesis, and energy-linked reduction of NAD+, while increasing hydrogen peroxide production, which may form reactive oxygen species and oxidative stress.
Contaminant Sources
  • IARC Carcinogens Group 3
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Arsenic Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organometallic
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC18H15As
Average Molecular Mass306.233 g/mol
Monoisotopic Mass306.039 g/mol
CAS Registry Number603-32-7
IUPAC Nametriphenylarsane
Traditional Nametriphenylarsine
SMILESC1=CC=C(C=C1)[As](C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C18H15As/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
InChI KeyBPLUKJNHPBNVQL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Tertiary arsine
  • Trivalent organic arsenic compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organoarsenic compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceColorless solid.
Experimental Properties
PropertyValue
Melting Point61°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0013 g/LALOGPS
logP5.43ALOGPS
logP5.56ChemAxon
logS-5.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity76.42 m³·mol⁻¹ChemAxon
Polarizability29.74 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-667b2f8a8e70930e9064Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0039000000-5e8da9df4fe47d350cddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1049000000-b5b085de41e11c223f03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000000-83cd1a6dd868e2d03e26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0019000000-f24071fac6ae99808830Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-6192000000-040a6bb8c3f371a91407Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-1921000000-aa3360fe27894a68805bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (2) ; inhalation (2) ; dermal (2)
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. (8, 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. (3)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (6)
Uses/SourcesTriphenylarsine is used as a ligand and a reagent in coordination chemistry and organic synthesis. (7)
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (5) Chronic Oral: 0.0003 mg/kg/day (5) Chronic Inhalation: 0.01 mg/m3 (5)
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. (8, 3)
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
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. (3)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTriphenylarsine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID11773
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available