IMAZETHAPYR

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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 XVOKUMIPKHGGTN-UHFFFAOYSA-N
Smiles CCc1cnc(C2=NC(C)(C(C)C)C(=O)N2)c(c1)C(=O)O
InChI
InChI=1S/C15H19N3O3/c1-5-9-6-10(13(19)20)11(16-7-9)12-17-14(21)15(4,18-12)8(2)3/h6-8H,5H2,1-4H3,(H,19,20)(H,17,18,21)

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H19N3O3
Molecular Weight 289.33
AlogP 2.26
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 91.65
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 21.0
Assay Description Organism Bioactivity Reference
Increase in lignin content in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 10 days post onset of compound treatment Pisum sativum None
Induction of PAL activity in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment Pisum sativum None
Induction of DAHPS enzyme expression in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by immunoblot Pisum sativum None
Induction of ferulic acid accumulation in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method Pisum sativum None
Induction of caffeic acid accumulation in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method Pisum sativum None
Induction of p-coumaric acid accumulation in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method Pisum sativum None
Reduction in sinapic acid accumulation in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 3 to 10 days post onset of compound treatment by HPLC method Pisum sativum None
Induction of sinapic acid accumulation in Pisum sativum (pea) leaves at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method Pisum sativum None
Induction of ferulic acid accumulation in Pisum sativum (pea) leaves at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method Pisum sativum None
Induction of caffeic acid accumulation in Pisum sativum (pea) leaves at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method Pisum sativum None
Induction of p-coumaric acid accumulation in Pisum sativum (pea) leaves at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method Pisum sativum None
Growth inhibition in Pisum sativum (pea) at 69 uM added to nutrient medium measured 22 to 23 days post onset of compound treatment Pisum sativum None
Reduction of root hair growth in Zea mays (maize) seedlings at 400 ug/L measured 48 hr post dose by microscopy Zea mays None
Reduction in root tips in Zea mays (maize) seedlings at 100 to 800 ug/L Zea mays None
Effect on root surface area in Zea mays (maize) seedlings at 100 to 800 ug/L Zea mays None
Effect on root volume in Zea mays (maize) seedlings at 100 to 800 ug/L Zea mays None
Increase in root diameter in Zea mays (maize) seedlings at 100 to 800 ug/L Zea mays None
Phytotoxicity in Zea mays assessed (maize) as total root length measured per plant at 400 ug/L measured 5 days post compound treatment (Rvb = 12.32 +/- 1.46 cm) Zea mays 5.5 cm
Phytotoxicity in Zea mays assessed (maize) as total root length measured per plant at 800 ug/L measured 5 days post compound treatment (Rvb = 12.32 +/- 1.46 cm) Zea mays 5.2 cm
Phytotoxicity in Zea mays assessed (maize) as total root length measured per plant at 200 ug/L measured 5 days post compound treatment (Rvb = 12.32 +/- 1.46 cm) Zea mays 7.4 cm
Phytotoxicity in Zea mays (maize) assessed as shoot height at 800 ug/L measured 5 days post compound treatment (Rvb = 6.89 +/- 0.30 cm) Zea mays 4.0 cm
Phytotoxicity in Zea mays (maize) assessed as total root length measured per plant at 100 ug/L measured 5 days post compound treatment (Rvb = 12.32 +/- 1.46 cm) Zea mays 8.1 cm
Phytotoxicity in Zea mays (maize) assessed as shoot height at 200 ug/L measured 5 days post compound treatment (Rvb = 6.89 +/- 0.30 cm) Zea mays 6.2 cm
Phytotoxicity in Zea mays (maize) assessed as shoot height at 400 ug/L measured 5 days post compound treatment (Rvb = 6.89 +/- 0.30 cm) Zea mays 4.6 cm
Phytotoxicity in Zea mays (maize) assessed as shoot height at 100 ug/L measured 5 days post compound treatment (Rvb = 6.89 +/- 0.30 cm) Zea mays 6.3 cm
Phytotoxicity in Zea mays (maize) assessed as root dry weight assessed per 10 plants at 800 ug/L measured 5 days post compound treatment (Rvb = 42.8 +/- 0.7 mg) Zea mays 29.0 mg
Phytotoxicity in Zea mays (maize) assessed as root dry weight assessed per 10 plants at 200 ug/L measured 5 days post compound treatment (Rvb = 42.8 +/- 0.7 mg) Zea mays 34.6 mg
Phytotoxicity in Zea mays (maize) assessed as root dry weight assessed per 10 plants at 400 ug/L measured 5 days post compound treatment (Rvb = 42.8 +/- 0.7 mg) Zea mays 26.4 mg
Phytotoxicity in Zea mays (maize) assessed as root dry weight assessed per 10 plants at 100 ug/L measured 5 days post compound treatment (Rvb = 42.8 +/- 0.7 mg) Zea mays 36.1 mg
Phytotoxicity in Zea mays (maize) assessed as shoot dry weight assessed per 10 plants at 400 ug/L measured 5 days post compound treatment (Rvb = 101.2 +/- 4.5 mg) Zea mays 83.3 mg
Phytotoxicity in Zea mays (maize) assessed as shoot dry weight assessed per 10 plants at 800 ug/L measured 5 days post compound treatment (Rvb = 101.2 +/- 4.5 mg) Zea mays 73.4 mg
Phytotoxicity in Zea mays (maize) assessed as shoot dry weight assessed per 10 plants at 200 ug/L measured 5 days post compound treatment (Rvb = 101.2 +/- 4.5 mg) Zea mays 107.8 mg
Phytotoxicity in Zea mays (maize) assessed as shoot dry weight assessed per 10 plants at 100 ug/L measured 5 days post compound treatment (Rvb = 101.2 +/- 4.5 mg) Zea mays 92.4 mg
Inhibition of in vitro ALS activity in first leaf of the plant grew out Zea mays (maize) seedlings measured at 520 OD/ mg of protein/hr at 800 ug/L at 37 degC Zea mays 1.9 /hr
Inhibition of in vitro ALS activity in first leaf of the plant grew out Zea mays (maize) seedlings measured at 520 OD/ mg of protein/hr at 400 ug/L at 37 degC Zea mays 2.26 /hr
Inhibition of in vitro ALS activity in first leaf of the plant grew out Zea mays (maize) seedlings measured at 520 OD/ mg of protein/hr at 200 ug/L at 37 degC Zea mays 4.41 /hr
Inhibition of in vitro ALS activity of Zea mays (maize) at 25 mg/L at 37 degC Zea mays None
Inhibition of in vitro ALS activity in first leaf of the plant grew out Zea mays (maize) seedlings measured at 520 OD/ mg of protein/hr at 100 ug/L at 37 degC Zea mays 7.6 /hr
Inhibition of in vitro ALS activity of Zea mays (maize) at 200 ug/L at 37 degC Zea mays 19.8 %
Phytotoxicity against Phaseolus vulgaris (white beans) assessed as reduction in plant height applied pre-emergence relative to control Phaseolus vulgaris 40.0 %
Phytotoxicity against Phaseolus vulgaris (black beans) assessed as reduction in plant height applied pre-emergence relative to control Phaseolus vulgaris 40.0 %
Phytotoxicity against Phaseolus vulgaris (white beans) assessed as crop injury Phaseolus vulgaris 11.0 %
Phytotoxicity against Phaseolus vulgaris (kidney bean) assessed as crop injury Phaseolus vulgaris 2.0 %
Phytotoxicity against Phaseolus vulgaris (White dry bean) assessed as reduction in plant height applied pre-emergence relative to control Phaseolus vulgaris 40.0 %
Phytotoxicity against Phaseolus vulgaris (Black dry bean) assessed as reduction in plant height applied pre-emergence relative to control Phaseolus vulgaris 40.0 %
Phytotoxicity against Phaseolus vulgaris (White dry bean) assessed as visual crop injury applied post-emergence relative to control Phaseolus vulgaris 11.0 %
Phytotoxicity against Phaseolus vulgaris (Kidney dry bean) assessed as visual crop injury applied post-emergence relative to control Phaseolus vulgaris 1.8 %
Increase in Phaseolus vulgaris (otebo bean) yield at 150 g ai/ha applied as spray during pre-emergence treatment for 1 to 2 days (Rvb = 3.8 t/ha) Phaseolus vulgaris 2.9 tons/ha
Increase in Phaseolus vulgaris (otebo bean) yield at 75 g ai/ha applied as spray during pre-emergence treatment for 1 to 2 days (Rvb = 3.8 t/ha) Phaseolus vulgaris 3.2 tons/ha
Phytotoxicity in Phaseolus vulgaris (black bean) assessed as reduction in crop yield treated through soil application relative to control Phaseolus vulgaris 49.0 %
Phytotoxicity in Phaseolus vulgaris (cranberry bean) assessed as visual injury at 0.075 to 0.15 kg/ha applied prior to planting relative to control Phaseolus vulgaris 5.0 %
Phytotoxicity in Phaseolus vulgaris (dry bean) assessed as visual injury relative to control Phaseolus vulgaris 20.0 %
Phytotoxicity in Phaseolus vulgaris (pinto bean) assessed as visual injury at 75 g ai/ha applied prior to planting relative to control Phaseolus vulgaris 6.0 %
Phytotoxicity in Phaseolus vulgaris (otebo bean) assessed as change in moisture content at 75 to 150 g ai/ha applied as spray during preemergence treatment for 1 to 2 days Phaseolus vulgaris None
Phytotoxicity in Phaseolus vulgaris (otebo bean) assessed as shoot dry weight at 150 g ai/ha applied as spray during pre-emergence treatment for 1 to 2 days measured 42 days post emergence (Rvb = 164 g) Phaseolus vulgaris 95.0 g
Phytotoxicity in Phaseolus vulgaris (otebo bean) assessed as shoot dry weight at 75 g ai/ha applied as spray during pre-emergence treatment for 1 to 2 days measured 42 days post emergence (Rvb = 164 g) Phaseolus vulgaris 118.0 g
Phytotoxicity in Phaseolus vulgaris (otebo bean) assessed as plant height at 150 g ai/ha applied as spray during pre-emergence treatment for 1 to 2 days measured 28 days post emergence (Rvb = 29 cm) Phaseolus vulgaris 22.0 cm
Phytotoxicity in Phaseolus vulgaris (otebo bean) assessed as visual injury at 150 g ai/ha applied as spray during pre-emergence treatment for 1 to 2 days measured 28 days post emergence relative to untreated control Phaseolus vulgaris 16.0 %
Phytotoxicity in Phaseolus vulgaris (otebo bean) assessed as visual injury at 75 g ai/ha applied as spray during pre-emergence treatment for 1 to 2 days measured 28 days post emergence relative to untreated control Phaseolus vulgaris 6.0 %
Phytotoxicity in Phaseolus vulgaris (otebo bean) assessed as visual injury at 150 g ai/ha applied as spray during pre-emergence treatment for 1 to 2 days measured 14 days post emergence relative to untreated control Phaseolus vulgaris 1.0 %
Phytotoxicity in Phaseolus vulgaris (otebo bean) assessed as visual injury at 75 g ai/ha applied as spray during pre-emergence treatment for 1 to 2 days measured 14 days post emergence relative to untreated control Phaseolus vulgaris 0.0 %
Phytotoxicity in Phaseolus vulgaris (otebo bean) assessed as visual injury at 150 g ai/ha applied as spray during pre-emergence treatment for 1 to 2 days measured 7 days post emergence relative to untreated control Phaseolus vulgaris 0.0 %
Phytotoxicity in Phaseolus vulgaris (otebo bean) assessed as visual injury at 75 g ai/ha applied as spray during pre-emergence treatment for 1 to 2 days measured 7 days post emergence relative to untreated control Phaseolus vulgaris 0.0 %
Phytotoxicity in Phaseolus vulgaris (otebo bean) assessed as plant height at 75 g ai/ha applied as spray during pre-emergence treatment for 1 to 2 days measured 28 days post emergence (Rvb = 29 cm) Phaseolus vulgaris 26.0 cm
Phytotoxicity in Phaseolus vulgaris (black bean) assessed as visual injury treated through soil application relative to control Phaseolus vulgaris 6.0 %
Phytotoxicity in Phaseolus vulgaris (cranberry bean) assessed as visual injury at 0.075 to 0.15 kg/ha applied during pre-emergence relative to control Phaseolus vulgaris 5.0 %
Inhibition of ALS in ALS-herbicide-susceptible Raphanus raphanistrum WARR33 (wild radish) Raphanus raphanistrum 1353.0 nM
Resistance index, ratio of I50 for ALS Ala122Tyr mutant in ALS-herbicide-resistant Raphanus raphanistrum WARR30 (wild radish) expressing ALS Ala122Tyr mutant to I50 for ALS-herbicide-susceptible Raphanus raphanistrum (wild radish) Raphanus raphanistrum 741.0
Inhibition of ALS in ALS-herbicide-susceptible Raphanus raphanistrum WARR7 (wild radish) Raphanus raphanistrum 1353.0 nM
Inhibition of ALS Ala122Tyr mutant in ALS-herbicide-resistant Raphanus raphanistrum WARR30 (wild radish) expressing ALS Ala122Tyr mutant Raphanus raphanistrum 1000000.0 nM
Herbicidal activity against two to three leaf stage ALS-herbicide-susceptible Raphanus raphanistrum WARR7 (wild radish) assessed as reduction in dry weight of above-ground biomass measured 3 weeks after compound treatment Raphanus raphanistrum None
Herbicidal activity against two to three leaf stage ALS-herbicide-resistant Raphanus raphanistrum WARR30 (wild radish) expressing ALS Ala122Tyr mutant assessed as reduction in dry weight of above-ground biomass measured 3 weeks after compound treatment Raphanus raphanistrum None
Herbicidal activity against two to three leaf stage ALS-herbicide-susceptible Raphanus raphanistrum WARR7 (wild radish) assessed as reduction in survival measured 3 weeks after compound treatment Raphanus raphanistrum None
Herbicidal activity against two to three leaf stage ALS-herbicide-resistant Raphanus raphanistrum WARR30 (wild radish) expressing ALS Ala122Tyr mutant assessed as reduction in survival measured 3 weeks after compound treatment Raphanus raphanistrum None

Cross References

Resources Reference
ChEMBL CHEMBL1903400
SureChEMBL SCHEMBL18516
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