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Showing NP-Card for dinotefuran (NP0302683)

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Record Information
Version2.0
Created at2022-09-10 16:25:34 UTC
Updated at2022-09-10 16:25:34 UTC
NP-MRD IDNP0302683
Secondary Accession NumbersNone
Natural Product Identification
Common Namedinotefuran
DescriptionDinotefuran, also known as MTI 446, belongs to the class of organic compounds known as nitroguanidines. These are organonitrogen compounds containing a nitro group, which is N-linked to a guanidine. Dinotefuran is also used in veterinary medicine as a flea and tick preventive for dogs and as a flea preventive for cats. In order to avoid harming beneficial insects such as bees, it should not be applied during bloom. Dinotefuran is a very strong basic compound (based on its pKa). In July 2013, the state of Oregon temporarily restricted the use of dinotefuran pending the results of an investigation into a large bee kill. Its mechanism of action involves disruption of the insect's nervous system by inhibiting nicotinic acetylcholine receptors. Current studies show dinotefuran is effective at controlling the invasive Spotted lanternfly, first found in Berks County, PA, in 2014. It is used in combination with pyriproxifen or permethrin. dinotefuran is found in Streptomyces canus. Dinotefuran is an insecticide of the neonicotinoid class developed by Mitsui Chemicals for control of insect pests such as aphids, whiteflies, thrips, leafhoppers, leafminers, sawflies, mole cricket, white grubs, lacebugs, billbugs, beetles, mealybugs, and cockroaches on leafy vegetables, in residential and commercial buildings, and for professional turf management.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0302683 (dinotefuran)


  Mrv1652307282022142D          

 14 14  0  0  0  0            999 V2000
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    4.4143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    4.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    4.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  4  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  2  0  0  0  0
 14  3  1  0  0  0  0
 14  5  1  0  0  0  0
M  END
Download

3D MOL for NP0302683 (dinotefuran)

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
    4.0157   -0.4782   -0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264   -1.0041   -1.0414 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5994   -0.4865   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4142   -1.1075   -1.1351 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872   -0.3456   -1.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3426    0.1194   -0.1019 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6040    0.9600   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263    0.8444    1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9889   -0.5078    1.4453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9819   -1.0408    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6294    0.6656    0.1467 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9788    0.6325    1.5109 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.4364    1.6434    2.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410   -0.4866    2.2876 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.4008    0.1541   -1.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9751    0.1851    0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547   -1.3005   -0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4280   -2.1361   -1.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5235   -1.0048   -1.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5388    0.4923   -2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6653    0.6753    0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3504    0.5161   -0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681    2.0061   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4207    1.4647    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1417    1.2345    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4935   -1.6841   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2520   -1.6302    1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    1.6193   -0.2307 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 14  1  0
 12 13  2  0
 10  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  1
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
M  CHG  2  12   1  14  -1
M  END
Download

3D SDF for NP0302683 (dinotefuran)


  Mrv1652307282022142D          

 14 14  0  0  0  0            999 V2000
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    4.4143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    4.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    4.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  4  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  2  0  0  0  0
 14  3  1  0  0  0  0
 14  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN=C(NCC1CCOC1)NN(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H14N4O3/c1-8-7(10-11(12)13)9-4-6-2-3-14-5-6/h6H,2-5H2,1H3,(H2,8,9,10)

> <INCHI_KEY>
YKBZOVFACRVRJN-UHFFFAOYSA-N

> <FORMULA>
C7H14N4O3

> <MOLECULAR_WEIGHT>
202.214

> <EXACT_MASS>
202.106590327

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
19.695544933480093

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N''-methyl-N-nitro-N'-[(oxolan-3-yl)methyl]guanidine

> <ALOGPS_LOGP>
0.05

> <JCHEM_LOGP>
-0.4319066162330579

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.759354008622305

> <JCHEM_PKA_STRONGEST_BASIC>
8.128226089207843

> <JCHEM_POLAR_SURFACE_AREA>
91.47000000000001

> <JCHEM_REFRACTIVITY>
50.69519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dinotefuran

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0302683 (dinotefuran)

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PDB for NP0302683 (dinotefuran)
HEADER    PROTEIN                                 28-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUL-20         0                                  
HETATM    1  C   UNK     0       2.393   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.060   6.700   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      -0.274   4.390   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -1.608   6.700   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      -1.608   8.240   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -2.941   9.010   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.274   9.010   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.830  -0.290   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3    6                                                       
CONECT    3    2   14                                                       
CONECT    4    6    9                                                       
CONECT    5    6   14                                                       
CONECT    6    2    4    5                                                  
CONECT    7    8    9   10                                                  
CONECT    8    1    7                                                       
CONECT    9    4    7                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    3    5                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0302683 (dinotefuran)
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SMILES for NP0302683 (dinotefuran)
CN=C(NCC1CCOC1)NN(=O)=O
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INCHI for NP0302683 (dinotefuran)
InChI=1S/C7H14N4O3/c1-8-7(10-11(12)13)9-4-6-2-3-14-5-6/h6H,2-5H2,1H3,(H2,8,9,10)
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View in JSmol
Synonyms
ValueSource
1-Methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidineChEBI
1-Methyl-2-nitro-3-((3-tetrahydrofuryl)methyl)guanidineMeSH
N''-methyl-N-nitro-n'-((tetrahydro-3-furanyl)methyl)guanidineMeSH
MTI 446MeSH
DinotefuranMeSH
Chemical FormulaC7H14N4O3
Average Mass202.2140 Da
Monoisotopic Mass202.10659 Da
IUPAC NameN''-methyl-N-nitro-N'-[(oxolan-3-yl)methyl]guanidine
Traditional Namedinotefuran
CAS Registry NumberNot Available
SMILES
CN=C(NCC1CCOC1)NN(=O)=O
InChI Identifier
InChI=1S/C7H14N4O3/c1-8-7(10-11(12)13)9-4-6-2-3-14-5-6/h6H,2-5H2,1H3,(H2,8,9,10)
InChI KeyYKBZOVFACRVRJN-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces canusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitroguanidines. These are organonitrogen compounds containing a nitro group, which is N-linked to a guanidine.
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassGuanidines  
Direct ParentNitroguanidines  
Alternative Parents
Substituents
  • Nitroguanidine
    • 

  • Nitramine
    • 

  • Tetrahydrofuran
    • 

  • Organic nitro compound
    • 

  • Dialkyl ether
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Allyl-type 1,3-dipolar organic compound
    • 

  • Carboximidamide
    • 

  • Organic oxygen compound
    • 

  • Organic zwitterion
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Imine
    • 

  • Organopnictogen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.05ALOGPS
logP-0.43ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)8.13ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.47 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.7 m³·mol⁻¹ChemAxon
Polarizability19.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC18509  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDinotefuran  
METLIN IDNot Available
PubChem Compound197701  
PDB IDNot Available
ChEBI ID39183  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]