NP-MRD: Showing NP-Card for thiamethoxam (NP0263214)

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Record Information

Version

2.0

Created at

2022-09-08 06:19:28 UTC

Updated at

2022-09-08 06:19:28 UTC

NP-MRD ID

NP0263214

Secondary Accession Numbers

None

Natural Product Identification

Common Name

thiamethoxam

Description

Thiamethoxam belongs to the class of organic compounds known as 2,5-disubstituted thiazoles. 2,5-Disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 2 and 5 only. The use of neonicotinoids has been linked in a range of studies to adverse ecological effects, including honey-bee colony collapse disorder (CCD) and loss of birds due to a reduction in insect populations. Thiamethoxam is a neonicotinoid insecticide, which is a class of neuro-active insecticides modeled after nicotine. Thiamethoxam is an extremely weak basic (essentially neutral) compound (based on its pKa). Neonicotinoids are currently used on corn, canola, cotton, sorghum, sugar beets and soybeans. Thiamethoxam is a potentially toxic compound. Acetylcholine is broken down by acetylcholinesterase to terminate signals from these receptors. In mammals, nicotinic acetylcholine receptors are located in cells of both the central and peripheral nervous systems. thiamethoxam is found in Streptomyces canus. Nicotinic acetylcholine receptors are activated by the neurotransmitter acetylcholine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652307282022212D          

 18 19  0  0  0  0            999 V2000
   -0.6078   -0.4741    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0597   -1.7840    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752   -1.7840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2897   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1101   -3.1499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4457   -2.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2662   -2.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7511   -2.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4155   -3.7311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9005   -4.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5951   -3.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2595   -4.5710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4390   -4.6572    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.1035   -5.4109    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.0459   -3.9898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  CHG  2  16   1  17  -1
M  END
> <DATABASE_ID>
NP0263214

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1COCN(CC2=CN=C(Cl)S2)\C1=N/[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3/b11-8-

> <INCHI_KEY>
NWWZPOKUUAIXIW-FLIBITNWSA-N

> <FORMULA>
C8H10ClN5O3S

> <MOLECULAR_WEIGHT>
291.715

> <EXACT_MASS>
291.019287608

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
25.741961998510796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z)-3-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine

> <ALOGPS_LOGP>
0.54

> <JCHEM_LOGP>
1.0676472073333338

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.40464253327561645

> <JCHEM_POLAR_SURFACE_AREA>
84.1

> <JCHEM_REFRACTIVITY>
64.8112

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiamethoxam

> <JCHEM_VEBER_RULE>
0

$$$$

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 Cl   UNK     0      -1.135  -0.885   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0      -1.135  -2.425   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       0.111  -3.330   0.000  0.00  0.00           S+0
HETATM    4  N   UNK     0      -2.380  -3.330   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -1.905  -4.795   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.365  -4.795   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.541  -6.041   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.072  -5.880   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.699  -4.473   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.230  -4.312   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.135  -5.558   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.509  -6.965   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.414  -8.211   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.978  -7.126   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.351  -8.533   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       0.819  -8.693   0.000  0.00  0.00           N+1
HETATM   17  O   UNK     0       0.193 -10.100   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0      -0.086  -7.448   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2    6                                                       
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    3    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
ACTARA 25 WG	MeSH
3-(2-chloro-Thiazol-5-ylmethyl)-5-methyl-(1,3,5)oxadiazinan-4-yldene-N-nitroamine	MeSH
Actara	MeSH

Chemical Formula

C₈H₁₀ClN₅O₃S

Average Mass

291.7150 Da

Monoisotopic Mass

291.01929 Da

IUPAC Name

(4Z)-3-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine

Traditional Name

thiamethoxam

CAS Registry Number

Not Available

SMILES

CN1COCN(CC2=CN=C(Cl)S2)\C1=N/[N+]([O-])=O

InChI Identifier

InChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3/b11-8-

InChI Key

NWWZPOKUUAIXIW-FLIBITNWSA-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 2,5-disubstituted thiazoles. 2,5-Disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 2 and 5 only.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Thiazoles

Direct Parent

2,5-disubstituted thiazoles

Alternative Parents

Substituents

2,5-disubstituted 1,3-thiazole
Aryl chloride
Aryl halide
Heteroaromatic compound
Guanidine
Organic nitro compound
Allyl-type 1,3-dipolar organic compound
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	0.54	ALOGPS
logP	1.07	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	0.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	84.1 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.81 m³·mol⁻¹	ChemAxon
Polarizability	25.74 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thiamethoxam

METLIN ID

Not Available

PubChem Compound

5485188

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for thiamethoxam (NP0263214)

MOL for NP0263214 (thiamethoxam)

3D MOL for NP0263214 (thiamethoxam)

3D SDF for NP0263214 (thiamethoxam)

3D-SDF for NP0263214 (thiamethoxam)

PDB for NP0263214 (thiamethoxam)

3D PDB for NP0263214 (thiamethoxam)

SMILES for NP0263214 (thiamethoxam)

INCHI for NP0263214 (thiamethoxam)

Structure for NP0263214 (thiamethoxam)

3D Structure for NP0263214 (thiamethoxam)