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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:22 UTC
Update Date2019-07-23 06:09:28 UTC
HMDB IDHMDB0031770
Secondary Accession Numbers
  • HMDB31770
Metabolite Identification
Common NameCarbofuran
DescriptionCarbofuran, also known as furadan or NEX, belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. Carbofuran is a moderately basic compound (based on its pKa). Carbofuran is a potentially toxic compound. In one study, the exposure of rats to sublethal amounts of carbofuran decreased testosterone by 88%, while the levels of progesterone, cortisol, and estradiol were significantly increased (1279%, 202%, and 150%, respectively). In December of that year, FMC Corp., the sole US manufacturer of carbofuran, announced that it had voluntarily requested that the United States Environmental Protection Agency cancel all but six of the previously allowed uses of that chemical as a pesticide. In a number of publicized incidents worldwide, carbofuran has also been used to poison domestic pets.
Structure
Data?1563862168
Synonyms
ValueSource
2,2-Dimethyl-2,3-dihydro-7-benzofuranyl N-methylcarbamateChEBI
2,3-Dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamateChEBI
FuradanChEBI
2,2-Dimethyl-2,3-dihydro-7-benzofuranyl N-methylcarbamic acidGenerator
2,3-Dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamic acidGenerator
2, 3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamateHMDB
2, 3-Dihydro-2,2-dimethylbenzofuranyl-7-N-methylcarbamateHMDB
2,2-Dimethyl-2,2-dihydrobenzofuranyl-7 N-methylcarbamateHMDB
2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl methylcarbamateHMDB
2,2-Dimethyl-2,3-dihydrobenzoduranyl-7-N-methylcarbamateHMDB
2,2-Dimethyl-7-coumaranyl N-methylcarbamateHMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranol methylcarbamateHMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranol N-methylcarbamateHMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranol, methylcarbamATEHMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamateHMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate, 9ciHMDB
2,3-Dihydro-2,2-dimethylbenzofuranyl-7-N-methylcarbamateHMDB
7-Benzofurano, 2,3-dihydro-2,2-dimethyl, methylcarbamateHMDB
7-Benzofuranol, 2,3-dihydro-2,2-dimethyl-, methylcarbamateHMDB
Bay 70143HMDB
BrifurHMDB
CarbodanHMDB
Carbofuran (pesticide/fertilizer mixture)HMDB
Carbofuran mixtureHMDB
CarbofuraneHMDB
ChinufurHMDB
CrisfuranHMDB
CuraterrHMDB
FMC 10242HMDB
FuracarbHMDB
Furadan 3gHMDB
Furadan 4FHMDB
Furadan 75 WPHMDB
Furadan gHMDB
FuradaneHMDB
FurodanHMDB
KarbofuranuHMDB
KenofuranHMDB
NEXHMDB
Niagaral 242HMDB
PillarfuranHMDB
RampartHMDB
Sipcam uk carbosip 5gHMDB
Tripart nexHMDB
YaltoxHMDB
Bayer 70143HMDB
70143, BayerHMDB
Chemical FormulaC12H15NO3
Average Molecular Weight221.2524
Monoisotopic Molecular Weight221.105193351
IUPAC Name1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]-N-methylmethanimidic acid
Traditional Namefuradan 4F
CAS Registry Number1563-66-2
SMILES
CN=C(O)OC1=CC=CC2=C1OC(C)(C)C2
InChI Identifier
InChI=1S/C12H15NO3/c1-12(2)7-8-5-4-6-9(10(8)16-12)15-11(14)13-3/h4-6H,7H2,1-3H3,(H,13,14)
InChI KeyDUEPRVBVGDRKAG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassCoumarans
Sub ClassNot Available
Direct ParentCoumarans
Alternative Parents
Substituents
  • Coumaran
  • Alkyl aryl ether
  • Benzenoid
  • Carboximidic acid derivative
  • Ether
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Imine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point150 - 152 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.32 mg/mL at 25 °CNot Available
LogP2.32Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.63 g/LALOGPS
logP2.78ALOGPS
logP2.62ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.78ChemAxon
pKa (Strongest Basic)2.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.05 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.12 m³·mol⁻¹ChemAxon
Polarizability23.28 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3900000000-18e09d501d9575f88e4eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-9520000000-e9e198ba719d3f5dc563Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0910000000-2fbd40352781317815d9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-59bdc6f8164dc530582dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-fb307ce637826c8f8ed1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-6d70f3e6615ca3686a4eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-1900000000-5cd3bdfd63ba91812779Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-3900000000-836e257234a48d1bc272Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-9450000000-041464b0cff1914c2a37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-7920000000-d29a536c8b5558db559fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-5900000000-d628afbe5626eb5f362bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-5960000000-5285d2526b8167ac57cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-3900000000-024fea1de94271528a38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-7900000000-c27e125887753684946fSpectrum
MSMass Spectrum (Electron Ionization)splash10-03dj-4900000000-3a22bac014009deaedf1Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008443
KNApSAcK IDNot Available
Chemspider ID2468
KEGG Compound IDC14291
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarbofuran
METLIN IDNot Available
PubChem Compound2566
PDB IDNot Available
ChEBI ID34611
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kamboj A, Kiran R, Sandhir R: Carbofuran-induced neurochemical and neurobehavioral alterations in rats: attenuation by N-acetylcysteine. Exp Brain Res. 2006 Apr;170(4):567-75. Epub 2005 Nov 24. [PubMed:16307259 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .