Showing Compound Card for Chlorfenapyr (CDB006286)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-07-28 20:25:00 UTC
Updated at2020-11-18 16:40:17 UTC
CannabisDB IDCDB006286
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameChlorfenapyr
DescriptionChlorfenapyr, also known as ac 303630 or pirate, belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. Chlorfenapyr is an extremely weak basic (essentially neutral) compound (based on its pKa). Chlorfenapyr is a potentially toxic compound. Skin contact with cyanide salts can irritate and produce sores. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Organic nitriles decompose into cyanide ions both in vivo and in vitro.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
AC 303630ChEBI
CL 303630ChEBI
PirateChEBI
Piric acidGenerator
Chemical FormulaC15H11BrClF3N2O
Average Molecular Weight407.613
Monoisotopic Molecular Weight405.969537953
IUPAC Name4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
Traditional Namepylon
CAS Registry Number122453-73-0
SMILES
CCOCN1C(=C(C#N)C(Br)=C1C(F)(F)F)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C15H11BrClF3N2O/c1-2-23-8-22-13(9-3-5-10(17)6-4-9)11(7-21)12(16)14(22)15(18,19)20/h3-6H,2,8H2,1H3
InChI KeyCWFOCCVIPCEQCK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassSubstituted pyrroles
Direct ParentPhenylpyrroles
Alternative Parents
Substituents
  • 2-phenylpyrrole
  • Chlorobenzene
  • Halobenzene
  • Aryl bromide
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Azacycle
  • Carbonitrile
  • Nitrile
  • Hydrocarbon derivative
  • Organobromide
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alkyl fluoride
  • Organopnictogen compound
  • Alkyl halide
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point100.5°CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.57ALOGPS
logP5.29ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area37.95 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity85.33 m³·mol⁻¹ChemAxon
Polarizability33.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9210000000-86fbbcacc652bd7061092014-09-20View Spectrum
Predicted GC-MSChlorfenapyr, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0003900000-2476c7d97224bea17c192016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054k-1009200000-b050af335cc96a820c1b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mk-1179000000-3904535afa1eaecbdcaf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2002900000-4e49bee7bfe535b808b62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003s-1039100000-fd7d508b3e5f8bbe94d12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056s-2139000000-2714d622407d3dc39ad32016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100.40 MHz, CDCl3, experimental)Spectrum
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 IDC18455
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorfenapyr
METLIN IDNot Available
PubChem Compound91778
PDB IDNot Available
ChEBI ID39347
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 ]