NP-MRD: Showing NP-Card for nitenpyram (NP0294187)

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Record Information

Version

2.0

Created at

2022-09-10 02:36:36 UTC

Updated at

2022-09-10 02:36:36 UTC

NP-MRD ID

NP0294187

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nitenpyram

Description

Nitenpyram, also known as TI 304, belongs to the class of organic compounds known as 2-halopyridines. These are organic compounds containing a pyridine ring substituted at the 2-position by a halogen atom. A nitenpyram in which the double bond has E configuration. nitenpyram is found in Streptomyces canus. Nitenpyram is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
    0.6206    2.3205    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2047    1.3143   -0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4068    0.1232   -0.2051 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224   -0.8429    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676   -0.5465    0.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5969   -0.9034   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9328   -0.6182   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4491    0.0003    0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1734    0.3312    0.9390 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6054    0.3289    1.8586 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785    0.0710    1.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015   -0.0898   -0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6359    0.9262   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258    0.7441   -0.8124 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.8052    1.6926   -0.5070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5427   -0.4152   -1.3318 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.3104   -1.4093   -0.4287 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9256   -2.0766    0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7141    2.4984    0.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1932    3.3417    0.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305    2.0314    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4240    1.8109   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1426    0.9931   -1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0895   -0.8500    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -1.8755    0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1464   -1.3836   -1.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640   -0.9128   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    0.3540    2.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2319    1.9360   -0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2269   -1.9464   -1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8066   -2.6561    0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2374   -1.4226    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2756   -2.8690    1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  2  0
 12 17  1  0
 17 18  1  0
 12  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  1  0
  5 11  2  0
 11 10  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
  6  5  1  0
 13 29  1  0
 17 30  1  0
 18 31  1  0
 18 32  1  0
 18 33  1  0
  2 22  1  0
  2 23  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 24  1  0
  4 25  1  0
 11 28  1  0
  7 27  1  0
  6 26  1  0
M  CHG  2  14   1  16  -1
M  END


  Mrv1572001261617232D          

 19 19  0  0  0  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  9  4  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  2  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 14 10  2  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 17 16  2  0  0  0  0
 18 16  2  0  0  0  0
 19  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0294187

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=C(NC)N(CC)CC1=CN=C(Cl)C=C1)N(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H15ClN4O2/c1-3-15(11(13-2)8-16(17)18)7-9-4-5-10(12)14-6-9/h4-6,8,13H,3,7H2,1-2H3/b11-8+

> <INCHI_KEY>
CFRPSFYHXJZSBI-DHZHZOJOSA-N

> <FORMULA>
C11H15ClN4O2

> <MOLECULAR_WEIGHT>
270.72

> <EXACT_MASS>
270.0883534

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.519883264556956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(E)-1-{[(6-chloropyridin-3-yl)methyl](ethyl)amino}-2-nitroethenyl](methyl)amine

> <ALOGPS_LOGP>
0.57

> <JCHEM_LOGP>
1.8735555403333335

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.4998041876101573

> <JCHEM_POLAR_SURFACE_AREA>
73.98

> <JCHEM_REFRACTIVITY>
80.76529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nitenpyram

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-JAN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-JAN-16         0                                  
HETATM    1  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
HETATM   13  N   UNK     0      -2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -2.667   0.000   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2   13                                                            
CONECT    3    1   15                                                       
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    9   14                                                       
CONECT    7    9   15                                                       
CONECT    8   11   16   19                                                  
CONECT    9    4    6    7                                                  
CONECT   10    5   12   14                                                  
CONECT   11    8   13   15                                                  
CONECT   12   10                                                            
CONECT   13    2   11                                                       
CONECT   14    6   10                                                       
CONECT   15    3    7   11                                                  
CONECT   16    8   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    8                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
(1E)-N-((6-Chloro-3-pyridinyl)methyl)-N-ethyl-n'-methyl-2-nitro-1,1-ethenediamine	ChEBI
TI 304	ChEBI
Nitenpyram	ChEBI
(e)-N-(6-Chloro-3-pyridylmethyl)-N-ethyl-n'-methyl-2-nitrovinylidenediamine	MeSH

Chemical Formula

C₁₁H₁₅ClN₄O₂

Average Mass

270.7200 Da

Monoisotopic Mass

270.08835 Da

IUPAC Name

[(E)-1-{[(6-chloropyridin-3-yl)methyl](ethyl)amino}-2-nitroethenyl](methyl)amine

Traditional Name

nitenpyram

CAS Registry Number

Not Available

SMILES

[H]C(=C(NC)N(CC)CC1=CN=C(Cl)C=C1)N(=O)=O

InChI Identifier

InChI=1S/C11H15ClN4O2/c1-3-15(11(13-2)8-16(17)18)7-9-4-5-10(12)14-6-9/h4-6,8,13H,3,7H2,1-2H3/b11-8+

InChI Key

CFRPSFYHXJZSBI-DHZHZOJOSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Streptomyces canus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-halopyridines. These are organic compounds containing a pyridine ring substituted at the 2-position by a halogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Halopyridines

Direct Parent

2-halopyridines

Alternative Parents

Substituents

2-halopyridine
Aryl chloride
Aryl halide
Heteroaromatic compound
C-nitro compound
Organic nitro compound
Secondary aliphatic amine
Organic oxoazanium
Secondary amine
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organonitrogen compound
Organochloride
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Amine
Organohalogen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

chloropyridyl insecticide (CHEBI:39170 )
nitenpyram (CHEBI:39170 )
Neonicotinoid insecticides (C18511 )

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	0.57	ALOGPS
logP	1.87	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	73.98 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	80.77 m³·mol⁻¹	ChemAxon
Polarizability	26.52 Å³	ChemAxon
Number of Rings	1	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

Not Available

DrugBank ID

DB11438

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C18511

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nitenpyram

METLIN ID

Not Available

PubChem Compound

3034287

PDB ID

Not Available

ChEBI ID

39170

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for nitenpyram (NP0294187)

MOL for NP0294187 (nitenpyram)

3D MOL for NP0294187 (nitenpyram)

3D SDF for NP0294187 (nitenpyram)

3D-SDF for NP0294187 (nitenpyram)

PDB for NP0294187 (nitenpyram)

3D PDB for NP0294187 (nitenpyram)

SMILES for NP0294187 (nitenpyram)

INCHI for NP0294187 (nitenpyram)

Structure for NP0294187 (nitenpyram)

3D Structure for NP0294187 (nitenpyram)