Np mrd loader

Record Information
Version2.0
Created at2022-09-04 16:00:48 UTC
Updated at2022-09-04 16:00:48 UTC
NP-MRD IDNP0197703
Secondary Accession NumbersNone
Natural Product Identification
Common Nametransfluthrin
DescriptionTransfluthrin belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Transfluthrin is an extremely weak basic (essentially neutral) compound (based on its pKa). transfluthrin was first documented in 2006 (PMID: 16552726). A carboxylic ester obtained by formal condensation of 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and 2,3,5,6-tetrafluorobenzyl alcohol (PMID: 20410569) (PMID: 21377505) (PMID: 21736273).
Structure
Thumb
Synonyms
ValueSource
(2,3,5,6-Tetrafluorophenyl)methyl(1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylateChEBI
(2,3,5,6-Tetrafluorophenyl)methyl(1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
(2,3,5,6-Tetrafluorophenyl)methyl (1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acidGenerator
TransfluthrinMeSH
Chemical FormulaC15H12Cl2F4O2
Average Mass371.1500 Da
Monoisotopic Mass370.01505 Da
IUPAC Name(2,3,5,6-tetrafluorophenyl)methyl (1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Traditional Nametransfluthrin
CAS Registry NumberNot Available
SMILES
[H][C@@]1(C=C(Cl)Cl)[C@@]([H])(C(=O)OCC2=C(F)C(F)=CC(F)=C2F)C1(C)C
InChI Identifier
InChI=1S/C15H12Cl2F4O2/c1-15(2)7(3-10(16)17)11(15)14(22)23-5-6-12(20)8(18)4-9(19)13(6)21/h3-4,7,11H,5H2,1-2H3/t7-,11+/m1/s1
InChI KeyDDVNRFNDOPPVQJ-HQJQHLMTSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyloxycarbonyls
Direct ParentBenzyloxycarbonyls
Alternative Parents
Substituents
  • Benzyloxycarbonyl
  • Fluorobenzene
  • Halobenzene
  • Aryl fluoride
  • Aryl halide
  • Cyclopropanecarboxylic acid or derivatives
  • Carboxylic acid ester
  • Ketene acetal or derivatives
  • Carboxylic acid derivative
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP4.83ALOGPS
logP4.77ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity88.91 m³·mol⁻¹ChemAxon
Polarizability30.59 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC13410
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTransfluthrin
METLIN IDNot Available
PubChem Compound656612
PDB IDNot Available
ChEBI ID32253
Good Scents IDNot Available
References
General References
  1. Pauluhn J, Mohr U: Mosquito coil smoke inhalation toxicity. Part II: subchronic nose-only inhalation study in rats. J Appl Toxicol. 2006 May-Jun;26(3):279-92. doi: 10.1002/jat.1139. [PubMed:16552726 ]
  2. Luo L, Shao B, Zhang J: Pressurized liquid extraction and cleanup procedure for the determination of pyrethroids in soils using gas chromatography/tandem mass spectrometry. Anal Sci. 2010;26(4):461-5. doi: 10.2116/analsci.26.461. [PubMed:20410569 ]
  3. Yokohira M, Arnold LL, Lautraite S, Sheets L, Wason S, Stahl B, Eigenberg D, Pennington KL, Kakiuchi-Kiyota S, Cohen SM: The effects of oral treatment with transfluthrin on the urothelium of rats and its metabolite, tetrafluorobenzoic acid on urothelial cells in vitro. Food Chem Toxicol. 2011 Jun;49(6):1215-23. doi: 10.1016/j.fct.2011.02.022. Epub 2011 Mar 4. [PubMed:21377505 ]
  4. Nazimek T, Wasak M, Zgrajka W, Turski WA: Content of transfluthrin in indoor air during the use of electro-vaporizers. Ann Agric Environ Med. 2011;18(1):85-8. [PubMed:21736273 ]
  5. LOTUS database [Link]