Showing Compound Card for Tetrachlorvinphos (CDB006251)

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Record Information
Version1.0
Created at2020-07-28 20:22:53 UTC
Updated at2020-11-18 16:40:16 UTC
CannabisDB IDCDB006251
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameTetrachlorvinphos
Descriptiontetrachlorvinphos, also known as gardona or stirofos, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. In 2014, the Natural Resources Defense Council (NRDC) filed a lawsuit against the United States Environmental Protection Agency (EPA) seeking EPA to respond to NRDC’s 2009 petition to ban tetrachlorvinphos in common pet flea treatment products. tetrachlorvinphos is an extremely weak basic (essentially neutral) compound (based on its pKa). Tetrachlorvinphos is slowly hydrolyzed in neutral and aqueous acidic media. Tetrachlorvinphos was originally registered for use on various food crops, livestock, pet animals, and in or around buildings. This is a listing of alternate names for this chemical, including trade names and synonyms. The chemical material may be absorbed through the skin and is a lachrymator. The substance is insoluble in water. It is a cholinesterase inhibitor and is a positive animal carcinogen.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Z)-2-Chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphateChEBI
2-Chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphateChEBI
GardonaChEBI
StirofosChEBI
StirophosChEBI
(Z)-2-Chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphoric acidGenerator
2-Chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphoric acidGenerator
[(Z)-2-chloro-1-(2,4,5-Trichlorophenyl)ethenyl] dimethyl phosphoric acidGenerator
RabonMeSH
TetrachlorvinphosMeSH
Chemical FormulaC10H9Cl4O4P
Average Molecular Weight365.95
Monoisotopic Molecular Weight363.8992566
IUPAC Name(Z)-2-chloro-1-(2,4,5-trichlorophenyl)ethenyl dimethyl phosphate
Traditional Namerabon
CAS Registry NumberNot Available
SMILES
[H]\C(Cl)=C(\OP(=O)(OC)OC)C1=CC(Cl)=C(Cl)C=C1Cl
InChI Identifier
InChI=1S/C10H9Cl4O4P/c1-16-19(15,17-2)18-10(5-11)6-3-8(13)9(14)4-7(6)12/h3-5H,1-2H3/b10-5-
InChI KeyUBCKGWBNUIFUST-YHYXMXQVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassStyrenes
Direct ParentStyrenes
Alternative Parents
Substituents
  • Styrene
  • Chlorobenzene
  • Halobenzene
  • Dialkyl phosphate
  • Aryl chloride
  • Aryl halide
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Organic oxygen compound
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.93ALOGPS
logP4.19ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)-9.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity76.69 m³·mol⁻¹ChemAxon
Polarizability29.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTetrachlorvinphos, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03gi-0906000000-50c011e020b530f7cff82016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0419000000-8c65b63cfb04361bca622016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2910000000-7fed324a7041fafa7bff2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0109000000-60d26ebab63f203436e12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03gi-1409000000-2bfacd593d7072e40aab2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9500000000-28693f4b7629c3d542482016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC14513
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrachlorvinphos
METLIN IDNot Available
PubChem Compound5284462
PDB IDNot Available
ChEBI ID35005
References
General References
  1. Moulins JR, Blais M, Montsion K, Tully J, Mohan W, Gagnon M, McRitchie T, Kwong K, Snider N, Blais DR: Multiresidue Method of Analysis of Pesticides in Medical Cannabis. J AOAC Int. 2018 Nov 1;101(6):1948-1960. doi: 10.5740/jaoacint.17-0495. Epub 2018 May 29. [PubMed:29843862 ]