AF-2 [2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamide] (CHEM016117)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:15:24 UTC
Update Date2016-11-09 01:15:20 UTC
Accession NumberCHEM016117
Identification
Common NameAF-2 [2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamide]
ClassSmall Molecule
DescriptionA member of the class of acrylamides that is acrylamide which is substituted at positions 2 and 3 by 2-furyl and 5-nitro-2-furyl groups, respectively (the trans isomer). Formerly used as a food preservative, it was withdrawn from the market following suspicions of carcenogenicity.
Contaminant Sources
  • IARC Carcinogens Group 2B
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamideChEBI
AF 2ChEBI
AF-2ChEBI
FurylfuramideChEBI
AF2MeSH
TofuronMeSH
Chemical FormulaC11H8N2O5
Average Molecular Mass248.194 g/mol
Monoisotopic Mass248.043 g/mol
CAS Registry Number3688-53-7
IUPAC Name(2Z)-2-(furan-2-yl)-3-(5-nitrofuran-2-yl)prop-2-enimidic acid
Traditional Namefurylfuramide
SMILES[H]\C(=C(\C(O)=N)C1=CC=CO1)C1=CC=C(O1)N(=O)=O
InChI IdentifierInChI=1S/C11H8N2O5/c12-11(14)8(9-2-1-5-17-9)6-7-3-4-10(18-7)13(15)16/h1-6H,(H2,12,14)/b8-6-
InChI KeyLYAHJFZLDZDIOH-VURMDHGXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrofurans. Nitrofurans are compounds containing a furan ring which bears a nitro group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurans
Sub ClassNitrofurans
Direct ParentNitrofurans
Alternative Parents
Substituents
  • 2-nitrofuran
  • Nitroaromatic compound
  • Heteroaromatic compound
  • Carboxamide group
  • C-nitro compound
  • Organic nitro compound
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Organic oxoazanium
  • Oxacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxygen compound
  • Organic zwitterion
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP1.54ALOGPS
logP-0.68ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)-1.8ChemAxon
pKa (Strongest Basic)10.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area116.18 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.63 m³·mol⁻¹ChemAxon
Polarizability23.14 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-ac410f2b03a5c51cdf01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-8b697d07a0fa9e480681Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9210000000-45562fc6959393c120cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-f43e57a8bc7bacf5af58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1090000000-2943b73bdcaeaeda8adaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-9000000000-4ff1d1535fa885f50777Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFurylfuramide
Chemspider IDNot Available
ChEBI ID15660
PubChem Compound ID5280707
Kegg Compound IDC19558
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available