Showing Compound Card for Fipronil (CDB006192)

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Record Information
Version1.0
Created at2020-07-28 20:14:53 UTC
Updated at2020-11-18 16:40:14 UTC
CannabisDB IDCDB006192
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFipronil
DescriptionFipronil belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. Based on a literature review very few articles have been published on Fipronil.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Amino-1-(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitileMeSH
Chemical FormulaC12H4Cl2F6N4OS
Average Molecular Weight437.148
Monoisotopic Molecular Weight435.938706104
IUPAC Name5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile
Traditional Namefipronil
CAS Registry Number120068-37-3
SMILES
NC1=C(C(=NN1C1=C(Cl)C=C(C=C1Cl)C(F)(F)F)C#N)S(=O)C(F)(F)F
InChI Identifier
InChI=1S/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2
InChI KeyZOCSXAVNDGMNBV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • Trifluoromethylbenzene
  • 1,3-dichlorobenzene
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Trihalomethane
  • Sulfoxide
  • Azacycle
  • Sulfinyl compound
  • Carbonitrile
  • Nitrile
  • Alkyl fluoride
  • Organonitrogen compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Organosulfur compound
  • Primary amine
  • Hydrocarbon derivative
  • Halomethane
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Alkyl halide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point200.5°CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0019 mg/mL at 20°C [TOMLIN,C (1997)]Not Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.4ALOGPS
logP4.49ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)0.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area84.7 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.66 m³·mol⁻¹ChemAxon
Polarizability31.6 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSFipronil, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFipronil, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 30V, positivesplash10-014i-0009000000-334b13092f28e3fec2e52020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 13V, positivesplash10-00kr-0008900000-9323fcb965734859dca32020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 26V, positivesplash10-014i-0029000000-e0abfbca9e3c21404e2e2020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 39V, positivesplash10-0udr-0090000000-f7a89980ca0ba058ebc42020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 52V, positivesplash10-0uk9-0090000000-774c92f3b5c696a2b92d2020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 65V, positivesplash10-0h99-0090000000-5daadc5c9b866be9d9692020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 78V, positivesplash10-000i-0390000000-98dad3fc291cebd5b2502020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 35V, positivesplash10-014i-0009000000-34b3700f2952e81571522020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 35V, positivesplash10-014i-0009000000-bb516888cbc97c7be4102020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 35V, positivesplash10-014i-0009000000-997cb32c3d6ddd079aa12020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 65V, positivesplash10-014i-0009000000-c8e20e8be0f7bf23ab332020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-003r-0006900000-7e2a16a8403fc19b5c862020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, negativesplash10-004i-0009000000-6fcca9a8920f4069a07b2020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, negativesplash10-004j-0298000000-e5b4a2f041e4729bdddf2020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, negativesplash10-003s-0391000000-4428966fce32d1360f4c2020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, negativesplash10-001i-0960000000-0efa5c7f8eb7eb83a2582020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 30V, negativesplash10-004j-0009000000-707b4841356803f9754b2020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 13V, negativesplash10-004i-0009200000-bc7b0dbfd3097ff342362020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 26V, negativesplash10-004i-0039000000-f2b91a8120f3ba256b462020-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-f562c603052e9b1cf5592016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0004900000-9f31da92517ecaab9b632016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2191000000-bdb48ae35693024eabbf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-d727fa54e3c5656179e92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0200900000-5e6ddc958202f2b2c0d62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mo-4490000000-e1ad4fbd38d1a8f3a2352016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0252265
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3235
KEGG Compound IDC11099
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFipronil
METLIN IDNot Available
PubChem Compound3352
PDB IDNot Available
ChEBI ID83394
References
General References
  1. Taylor A, Birkett JW: Pesticides in cannabis: A review of analytical and toxicological considerations. Drug Test Anal. 2020 Feb;12(2):180-190. doi: 10.1002/dta.2747. Epub 2020 Jan 19. [PubMed:31834671 ]