Source Gaulton A, Kale N, van Westen GJ, Bellis LJ, Bento AP, Davies M, Hersey A, Papadatos G, Forster M, Wege P, Overington JP. A large-scale crop protection bioassay data set. Sci Data. 2015 Jul 7;2:150032. Read more ...

Structure

InChI Key YKBZOVFACRVRJN-UHFFFAOYSA-N
Smiles CN\C(=N\CC1CCOC1)\N[N+](=O)[O-]
InChI
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C7H14N4O3
Molecular Weight 202.21
AlogP 1.6
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 91.47
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 14.0
Assay Description Organism Bioactivity Reference
Inhibition of Oryctolagus cuniculus (rabbit) AOX in liver cytosol at IC50 concentration Oryctolagus cuniculus 3.0 %
Inhibition of xanthine oxidase at IC50 concentration None 6.0 %
Inhibition of Agaricus bisporus (mushroom) tyrosinase at IC50 concentration Agaricus bisporus 3.0 %
Inhibition of xanthine oxidase None 1000000.0 nM
Inhibition of Oryctolagus cuniculus (rabbit) AOX in liver cytosol Oryctolagus cuniculus 1000000.0 nM
Inhibition of Agaricus bisporus (mushroom) tyrosinase Agaricus bisporus 1000000.0 nM
Phytotoxicity against Vitis vinifera seedlings assessed as lesions at 50 to 100 ppm after 9 days Vitis vinifera None
Phytotoxicity against Zea mays (maize) seedlings assessed as lesions at 50 to 100 ppm after 9 days Zea mays None
Phytotoxicity against Gossypium hirsutum (cotton) seedlings assessed as lesions at 50 to 100 ppm after 9 days Gossypium hirsutum None
Phytotoxicity against Glycine max (soybean) seedlings assessed as lesions in unfoliolate leaves at 100 ppm after 9 days Glycine max None
Insecticidal activity against Caelifera (grasshoppers) Caelifera None
Insecticidal activity against Siphonaptera (fleas) Siphonaptera None
Insecticidal activity against Diptera (houseflies) Diptera None
Insecticidal activity against Periplaneta americana (American cockroach) Periplaneta americana None
Insecticidal activity against Chrysomelidae (leaf beetles) Chrysomelidae None
Insecticidal activity against Diptera (leafminer flies) Diptera None
Insecticidal activity against Curculionidae (weevils) Curculionidae None
Insecticidal activity against Isoptera (termites) Isoptera None
Insecticidal activity against Alticini (flea beetles) Alticini None
Insecticidal activity against Plutella xylostella (diamondback moth) Plutella xylostella None
Insecticidal activity against Lepidoptera (peach fruit moth) Lepidoptera None
Insecticidal activity against Lepidoptera (rice borers) Lepidoptera None
Insecticidal activity against Thysanoptera (thrips) Thysanoptera None
Insecticidal activity against Lepidoptera (leafminers) Lepidoptera None
Insecticidal activity against Miridae (plant bugs) Miridae None
Insecticidal activity against Leptocorisa acuta (rice bugs) Leptocorisa acuta None
Insecticidal activity against Aphididae (aphids) Aphididae None
Insecticidal activity against Pseudococcidae (mealybugs) Pseudococcidae None
Insecticidal activity against Aleyrodidae (whiteflies) Aleyrodidae None
Insecticidal activity against Laodelphax striatella (small brown planthopper) Laodelphax striatella None
Lipophilicity, log P of the compound None -0.64
Insecticidal activity against Nephotettix cincticeps (green rice leafhopper) Nephotettix cincticeps None
Aqueous solubility of the compound None 54300.0 ug.mL-1
Binding affinity to Nephotettix cincticeps (green rice leafhopper) nicotinic acetylcholine receptor Nephotettix cincticeps None
Binding affinity to Laodelphax striatella (small brown planthopper) nicotinic acetylcholine receptor Laodelphax striatella None
Insecticidal activity against Nephotettix cincticeps (green rice leafhopper) assessed as lethality at 0.1 to 1 ppm Nephotettix cincticeps 70.0 %
Insecticidal activity against Laodelphax striatella (small brown planthopper) assessed as lethality at 0.1 to 1 ppm Laodelphax striatella 70.0 %
Insecticidal activity against adult Aphis gossypii (cotton aphid) in cucumber cotyledons assessed as mortality at 500 ppm treated for 5 secs before adult infestation measured after 72 hr Aphis gossypii 100.0 %
Displacement of [3H]IMI from nicotinic acetylcholine receptor in Drosophila melanogaster brain Drosophila melanogaster 76.0 nM
Insecticidal activity against 1 to 3 day-old adult Nephotettix cincticeps (green rice leafhopper) infested in compound-treated rice seedlings assessed as mortality measured after 3 days Nephotettix cincticeps 0.1 ppm
Insecticidal activity against 1 to 3 day-old adult Laodelphax striatella (small brown planthopper) infested compound-treated rice seedlings assessed as mortality measured after 3 days Laodelphax striatella 0.1 ppm
Insecticidal activity against 1 to 3 day-old adult Nephotettix cincticeps (green rice leafhopper) infested in compound-treated rice seedlings assessed as mortality measured after 3 days Nephotettix cincticeps 0.1 ppm
Insecticidal activity against 1 to 3 day-old adult Laodelphax striatella (small brown planthopper) infested compound-treated rice seedlings assessed as mortality measured after 3 days Laodelphax striatella 0.1 ppm
Ratio of IC50 for nicotinic acetylcholine receptor in Myzus persicae to IC50 for nicotinic acetylcholine receptor in Drosophila melanogaster None 5.6
Displacement of [3H]IMI from nicotinic acetylcholine receptor in Drosophila melanogaster head membrane after 90 min by filter binding assay Drosophila melanogaster 5000.0 nM
Displacement of [3H]IMI from nicotinic acetylcholine receptor in Myzus persicae (green peach aphid) whole body membrane after 90 min by filter binding assay Myzus persicae 5000.0 nM
Ratio of EC50 for Daphnia magna to EC50 for first instar larvae of Cheumatopsyche brevilineata None 4.97
Insecticidal activity against first-instar larvae of Cheumatopsyche brevilineata after 48 hr Cheumatopsyche 0.0104 ug.mL-1
Octanol-water partition coefficient, log KOW of the compound None -0.644
Insecticidal activity against Daphnia magna after 48 hr Daphnia magna 968.3 ug.mL-1
Resistance index, ratio of LC50 for neonicotinoid-resistant Myzus persicae FRC-P (green peach aphid) to LC50 for Myzus persicae 4106A Myzus persicae 54.0
Insecticidal activity against Myzus persicae 4106A (green peach aphid) fed on compound treated chinese cabbage discs after 72 hr Myzus persicae 10.0 ppm
Insecticidal activity against neonicotinoid-resistant Myzus persicae FRC-P (green peach aphid) fed on compound treated chinese cabbage discs after 72 hr Myzus persicae 538.0 ppm
Displacement of [3H]IMD from nAChR in Myzus persicae 4106A (green peach aphid) membrane after 70 min Myzus persicae 336.0 nM
Displacement of [3H]-methyl-SFX from nAChR in Myzus persicae 4106A (green peach aphid) membrane after 70 min Myzus persicae 3.2 nM
Agonist activity at Drosophila melanogaster SAD/chicken beta2 nAChR expressed in Xenopus laevis oocytes assessed as inward current by two-electrode voltageclamp technique relative to acetylcholine response None 1.04 %
Agonist activity at Drosophila melanogaster SAD/chicken beta2 nAChR expressed in Xenopus laevis oocytes assessed as inward current by two-electrode voltageclamp technique None None Agonist activity at Drosophila melanogaster SAD/chicken beta2 nAChR expressed in Xenopus laevis oocytes assessed as inward current by two-electrode voltageclamp technique None 223872.11 nM
Insecticidal activity against Popillia japonica assessed as mortality after 30 days Popillia japonica 86.2 %
Insecticidal activity against Popillia japonica assessed as mortality after 20 days Popillia japonica 69.3 %
Insecticidal activity against Popillia japonica assessed as mortality after 10 days Popillia japonica 54.4 %
Insecticidal activity against Maladera castanea assessed as mortality after 20 days Maladera castanea None
Insecticidal activity against Maladera castanea assessed as mortality after 30 days Maladera castanea None
Insecticidal activity against Maladera castanea assessed as mortality after 10 days Maladera castanea None
Insecticidal activity against Anomala orientalis assessed as mortality after 30 days Anomala orientalis None
Insecticidal activity against Anomala orientalis assessed as mortality after 20 days Anomala orientalis None
Insecticidal activity against Anomala orientalis assessed as mortality after 10 days Anomala orientalis None
Insecticidal activity against Amphimallon majalis (European chafer) assessed as mortality after 30 days Amphimallon majalis 8.9 %
Insecticidal activity against Amphimallon majalis (European chafer) assessed as mortality after 20 days Amphimallon majalis 2.2 %
Insecticidal activity against Amphimallon majalis (European chafer) assessed as mortality after 10 days Amphimallon majalis 0.0 %
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as fecundity at LC20 concentration Aphis gossypii None
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as longevity at LC20 concentration Aphis gossypii 2.95 day
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as inhibition of honeydew excretion at LC20 concentration measured after 72 hr by dipping method Aphis gossypii 82.2 %
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as reduction in body weight at LC20 concentration measured after 72 hr by dipping method (Rvb = 0.40 +/- 0.0002 mg/aphid) Aphis gossypii 0.09 mg
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as reduction in body weight at LC20 concentration measured after 48 hr by dipping method (Rvb = 0.36 +/- 0.0006 mg/aphid) Aphis gossypii 0.11 mg
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as mortality measured after 72 hr by dipping method Aphis gossypii 0.88 ug ml-1
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as reduction in body weight at LC20 concentration measured after 24 hr by dipping method (Rvb = 0.33 +/- 0.0004 mg/aphid) Aphis gossypii 0.13 mg
Resistance ratio, LC50 for Aphis gossypii RF45 (cotton aphid) to LC50 for Aphis gossypii SS Aphis gossypii 1.07
Insecticidal activity against imidacloprid-resistant Aphis gossypii RF45 (cotton aphid) in cotton leaves assessed as mortality measured after 48 hr by dipping method Aphis gossypii 1.29 microg/mL2
Insecticidal activity against Aphis gossypii SS (cotton aphid) in cotton leaves assessed as mortality measured after 48 hr by dipping method Aphis gossypii 1.2 microg/mL2
Toxicity in Daphnia pulex after 48 hr Daphnia pulex 1000.0 ppm
Toxicity in Cyprinus carpio (common carp) after 96 hr Cyprinus carpio 100.0 ppm
Acute toxicity in Anas platyrhynchos (mallard duck) dosed with diet Anas platyrhynchos 1301.0 mg.kg-1
Acute toxicity in po dosed Coturnix japonica (Japanese quail) Coturnix japonica 2000.0 mg.kg-1
Genotoxicity in Mus musculus (mouse) micronucleus Mus musculus None
Genotoxicity in Salmonella enterica subsp. enterica serovar Typhimurium by Ames test Salmonella enterica subsp. enterica serovar Typhimurium None
Carcinogenicity in Mus musculus (mouse) Mus musculus None
Carcinogenicity in Rattus norvegicus (rat) Rattus norvegicus None
Toxicity in po dosed Oryctolagus cuniculus (rabbit) assessed as teratogenicity Oryctolagus cuniculus None
Toxicity in po dosed Cavia porcellus (guinea pig) assessed as teratogenicity Cavia porcellus None
Toxicity in Cavia porcellus (guinea pig) assessed as skin sensitizing Cavia porcellus None
Toxicity in Oryctolagus cuniculus (rabbit) assessed as eye irritation Oryctolagus cuniculus None
Acute dermal toxicity in female Rattus norvegicus (rat) Rattus norvegicus 2000.0 mg.kg-1
Toxicity in female po dosed Mus musculus (mouse) Mus musculus 2275.0 mg.kg-1
Acute dermal toxicity in male Rattus norvegicus (rat) Rattus norvegicus 2000.0 mg.kg-1
Toxicity in male po dosed Mus musculus (mouse) Mus musculus 2450.0 mg.kg-1
Toxicity in female po dosed Rattus norvegicus (rat) Rattus norvegicus 2000.0 mg.kg-1
Solubility in water at pH 7 None 40000.0 ug.mL-1
Toxicity in male po dosed Rattus norvegicus (rat) Rattus norvegicus 2804.0 mg.kg-1
Octanol-water partition coefficient, log Pow of the compound None -0.549
Insecticidal activity against Thysanoptera (thrips) Thysanoptera None
Insecticidal activity against Dictyoptera Dictyoptera None
Insecticidal activity against Diptera (flies) Diptera None
Insecticidal activity against Coleoptera Coleoptera None
Insecticidal activity against Hemiptera (bugs) Hemiptera None
Insecticidal activity against Lepidoptera (butterflies and moths) Lepidoptera None
Insecticidal activity againstLaodelphax striatella (small brown planthopper) Laodelphax striatella None
Insecticidal activity against Nephotettix cincticeps (green rice leafhopper) Nephotettix cincticeps None

Cross References

Resources Reference
ChEMBL CHEMBL2228155
PubChem 197701
SureChEMBL SCHEMBL26337