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Record Information
Version2.0
Creation Date2014-09-17 20:02:27 UTC
Update Date2014-12-24 20:27:00 UTC
Accession NumberT3D4950
Identification
Common NameTris(2-chloroethyl)phosphate
ClassSmall Molecule
DescriptionTris(2-chloroethyl) phosphate (TCEP) is a chemical compound used as a flame retardant, plasticizer, and viscosity regulator in various types of polymers including polyurethanes, polyester resins, and polyacrylates. It was included in January 2011 in the European Chemicals Agency (ECHA) list of Substances of Very High Concern (SVHC) due to its being toxic for reproduction. Substances in the list of SVHCs are those for which ECHA is considering imposing a requirement for authorization for some or all uses.
Compound Type
  • Ester
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Plasticizer
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Phosphoric acid, tris(2-chloroethyl)ester
Tri(2-chloroethyl) phosphate
Tris(2-chloroethyl) orthophosphate
Tris(2-chloroethyl)phosphic acid
Tris(beta-chloroethyl) phosphate
Tris(chloroethyl)phosphate
Chemical FormulaC6H12Cl3O4P
Average Molecular Mass285.490 g/mol
Monoisotopic Mass283.954 g/mol
CAS Registry Number115-96-8
IUPAC Nametris(2-chloroethyl) phosphate
Traditional Nametris(2-chloroethyl)phosphate
SMILESClCCOP(=O)(OCCCl)OCCCl
InChI IdentifierInChI=1S/C6H12Cl3O4P/c7-1-4-11-14(10,12-5-2-8)13-6-3-9/h1-6H2
InChI KeyInChIKey=HQUQLFOMPYWACS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as trialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly three alkyl chains.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentTrialkyl phosphates
Alternative Parents
Substituents
  • Trialkyl phosphate
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoskeleton
  • Membrane
  • Microsome
  • Mitochondrial Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
Mismatch repairNot Availablemap03430
Cell cycleNot Availablemap04110
Base excision repairNot Availablemap03410
AnticonvulsantsNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.57 g/LALOGPS
logP1.36ALOGPS
logP2.11ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)-9.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity56.13 m³·mol⁻¹ChemAxon
Polarizability23.93 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0390000000-6775e4c721647a5a3e32JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03ka-9450000000-0b72b9ee93abd407ef94JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03l1-9460000000-384cbe62f62e1efaaed1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-008i-0190000000-b23aa0983b0f66b053b4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0960000000-5f457885a6c84a268fb5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-008i-0190000000-f26c6787ab96da8aab25JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03l0-6090000000-2ff653400988c9855017JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03l0-8290000000-817dc166ce8aa6781835JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-052e00872865bfaf0dfdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-9c8aaade1730674178f0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00e9-0590000000-3f032bbcfc9677fd9a57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-3910000000-0d7df033a49f8fb9a53eJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-06r2-9580000000-6cc979ed4f6998e16219JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (1)
Uses/SourcesTris(2-chloroethyl) phosphate is used as a flame retardant, plasticizer, and viscosity regulator in various types of polymers including polyurethanes, polyester resins, and polyacrylates.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound IDNot Available
ChEMBL IDCHEMBL1413786
ChemSpider ID7994
KEGG ID8295
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC031324
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4950.pdf
General References
  1. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Suzuki G, Tue NM, Malarvannan G, Sudaryanto A, Takahashi S, Tanabe S, Sakai S, Brouwer A, Uramaru N, Kitamura S, Takigami H: Similarities in the endocrine-disrupting potencies of indoor dust and flame retardants by using human osteosarcoma (U2OS) cell-based reporter gene assays. Environ Sci Technol. 2013 Mar 19;47(6):2898-908. doi: 10.1021/es304691a. Epub 2013 Mar 1. [23398518 ]