NP-MRD: Showing NP-Card for Carbofuran (NP0045130)

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Record Information

Version

2.0

Created at

2022-03-10 18:58:29 UTC

Updated at

2022-03-10 22:19:44 UTC

NP-MRD ID

NP0045130

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Carbofuran

Description

Carbofuran, also known as furadan 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 potentially toxic compound and is, in fact, one of the most toxic carbamate pesticides. It is manufactured by the reaction of methyl isocyanate with 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran. 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) (PMID: 20021136 ). The use of carbofuran on human consumable crops is currently banned in the U.S.A, Canada and the European Union. Carbofuran is a structural mimic of the neurohormone melatonin and could directly bind to MT2 melatonin receptor (Ki = 1.7 UM) (PMID: 28027439 ). Disruption of melatonin signaling could impact the circadian rhythm balance and is linked to elevated risk of developing diabetes. Carbofuran has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    4.9869   -0.9969    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5808   -0.8645    0.2621 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435   -1.3247    1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0559   -1.9738    2.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3490   -1.1344    0.6312 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8704    0.0858    0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6392    1.2181    0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0778    2.4237   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2403    2.4825   -0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228    1.3255   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4808    0.1298   -0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4055   -0.8966   -0.2078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6943   -0.3299   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4447   -1.1809   -1.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -0.1881    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4420    1.0655   -0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1372   -1.8373    1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3278   -0.0218    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5963   -1.1816   -0.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2987   -2.9423    2.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6709    1.2249    0.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    3.3055   -0.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943    3.4063   -0.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7267   -1.7560   -1.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0642   -1.9028   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0604   -0.5850   -2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2400   -1.0635    1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4569    0.0049    0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994    0.6746    1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1377    1.8085   -0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5362    1.0245   -2.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 11  6  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 14 24  1  0
 14 25  1  0
 14 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
M  END


  Mrv1652303202019002D          

 16 17  0  0  0  0            999 V2000
    0.6818    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
 10  8  2  0  0  0  0
 10  9  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  7  1  0  0  0  0
 13  3  1  4  0  0  0
 13 11  2  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 10  1  0  0  0  0
 16 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045130

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
DUEPRVBVGDRKAG-UHFFFAOYSA-N

> <FORMULA>
C12H15NO3

> <MOLECULAR_WEIGHT>
221.2524

> <EXACT_MASS>
221.105193351

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.279981980661212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]-N-methylmethanimidic acid

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.6230080726895824

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7807759066273388

> <JCHEM_PKA_STRONGEST_BASIC>
2.16441420910067

> <JCHEM_POLAR_SURFACE_AREA>
51.05000000000001

> <JCHEM_REFRACTIVITY>
60.115300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
furadan 4F

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       1.273   1.800   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.273  -0.260   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       7.454  -4.620   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4    5    6                                                       
CONECT    5    4    8                                                       
CONECT    6    4    9                                                       
CONECT    7    8   12                                                       
CONECT    8    5    7   10                                                  
CONECT    9    6   10   15                                                  
CONECT   10    8    9   16                                                  
CONECT   11   13   14   15                                                  
CONECT   12    1    2    7   16                                             
CONECT   13    3   11                                                       
CONECT   14   11                                                            
CONECT   15    9   11                                                       
CONECT   16   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
2,2-Dimethyl-2,3-dihydro-7-benzofuranyl N-methylcarbamate	ChEBI
2,3-Dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamate	ChEBI
Furadan	ChEBI
2,2-Dimethyl-2,3-dihydro-7-benzofuranyl N-methylcarbamic acid	Generator
2,3-Dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamic acid	Generator
2, 3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate	HMDB
2, 3-Dihydro-2,2-dimethylbenzofuranyl-7-N-methylcarbamate	HMDB
2,2-Dimethyl-2,2-dihydrobenzofuranyl-7 N-methylcarbamate	HMDB
2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl methylcarbamate	HMDB
2,2-Dimethyl-2,3-dihydrobenzoduranyl-7-N-methylcarbamate	HMDB
2,2-Dimethyl-7-coumaranyl N-methylcarbamate	HMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranol methylcarbamate	HMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranol N-methylcarbamate	HMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranol, methylcarbamATE	HMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate	HMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate, 9ci	HMDB
2,3-Dihydro-2,2-dimethylbenzofuranyl-7-N-methylcarbamate	HMDB
7-Benzofurano, 2,3-dihydro-2,2-dimethyl, methylcarbamate	HMDB
7-Benzofuranol, 2,3-dihydro-2,2-dimethyl-, methylcarbamate	HMDB
Bay 70143	HMDB
Brifur	HMDB
Carbodan	HMDB
Carbofuran (pesticide/fertilizer mixture)	HMDB
Carbofuran mixture	HMDB
Carbofurane	HMDB
Chinufur	HMDB
Crisfuran	HMDB
Curaterr	HMDB
FMC 10242	HMDB
Furacarb	HMDB
Furadan 3g	HMDB
Furadan 4F	HMDB
Furadan 75 WP	HMDB
Furadan g	HMDB
Furadane	HMDB
Furodan	HMDB
Karbofuranu	HMDB
Kenofuran	HMDB
NEX	HMDB
Niagaral 242	HMDB
Pillarfuran	HMDB
Rampart	HMDB
Sipcam uk carbosip 5g	HMDB
Tripart nex	HMDB
Yaltox	HMDB
Bayer 70143	HMDB
70143, Bayer	HMDB

Chemical Formula

C₁₂H₁₅NO₃

Average Mass

221.2524 Da

Monoisotopic Mass

221.10519 Da

IUPAC Name

1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]-N-methylmethanimidic acid

Traditional Name

furadan 4F

CAS Registry Number

1563-66-2

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 Key

DUEPRVBVGDRKAG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cannabis sativa	NULL	Not Available

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:34611 )
1-benzofurans (CHEBI:34611 )
Carbamate insecticides (C14291 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.78	ALOGPS
logP	2.62	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	2.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.12 m³·mol⁻¹	ChemAxon
Polarizability	23.28 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031770

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008443

KNApSAcK ID

Not Available

Chemspider ID

2468

KEGG Compound ID

C14291

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carbofuran

METLIN ID

Not Available

PubChem Compound

2566

PDB ID

Not Available

ChEBI ID

34611

Good Scents ID

Not Available

References

General References

Goad RT, Goad JT, Atieh BH, Gupta RC: Carbofuran-induced endocrine disruption in adult male rats. Toxicol Mech Methods. 2004;14(4):233-9. doi: 10.1080/15376520490434476. [PubMed:20021136 ]
Popovska-Gorevski M, Dubocovich ML, Rajnarayanan RV: Carbamate Insecticides Target Human Melatonin Receptors. Chem Res Toxicol. 2017 Feb 20;30(2):574-582. doi: 10.1021/acs.chemrestox.6b00301. Epub 2017 Jan 11. [PubMed:28027439 ]
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. doi: 10.1007/s00221-005-0241-5. Epub 2005 Nov 24. [PubMed:16307259 ]

Showing NP-Card for Carbofuran (NP0045130)

MOL for NP0045130 (Carbofuran)

3D MOL for NP0045130 (Carbofuran)

3D SDF for NP0045130 (Carbofuran)

3D-SDF for NP0045130 (Carbofuran)

PDB for NP0045130 (Carbofuran)

3D PDB for NP0045130 (Carbofuran)

SMILES for NP0045130 (Carbofuran)

INCHI for NP0045130 (Carbofuran)

Structure for NP0045130 (Carbofuran)

3D Structure for NP0045130 (Carbofuran)