SKIMMIANINE

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Synonyms
UNII 4E1KLC380B
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 SLSIBLKBHNKZTB-UHFFFAOYSA-N
Smiles COc1ccc2c(OC)c3ccoc3nc2c1OC
InChI
InChI=1S/C14H13NO4/c1-16-10-5-4-8-11(13(10)18-3)15-14-9(6-7-19-14)12(8)17-2/h4-7H,1-3H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H13NO4
Molecular Weight 259.26
AlogP 2.47
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 3.0
Polar Surface Area 53.72
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 19.0
Assay Description Organism Bioactivity Reference
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks after 3 days by flour disk bioassay Tribolium castaneum 75.71 ppm
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks after 3 days by flour disk bioassay Sitophilus zeamais 129.72 ppm
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks at 1000 ppm after 3 days by flour disk bioassay Tribolium castaneum 89.56 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks at 300 ppm after 3 days by flour disk bioassay Tribolium castaneum 68.62 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks at 100 ppm after 3 days by flour disk bioassay Tribolium castaneum 57.45 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks at 30 ppm after 3 days by flour disk bioassay Tribolium castaneum 30.12 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks at 10 ppm after 3 days by flour disk bioassay Tribolium castaneum 13.21 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks at 3 ppm after 3 days by flour disk bioassay Tribolium castaneum 4.31 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks at 1000 ppm after 3 days by flour disk bioassay Sitophilus zeamais 82.43 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks at 300 ppm after 3 days by flour disk bioassay Sitophilus zeamais 60.24 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks at 100 ppm after 3 days by flour disk bioassay Sitophilus zeamais 47.32 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks at 30 ppm after 3 days by flour disk bioassay Sitophilus zeamais 26.12 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks at 10 ppm after 3 days by flour disk bioassay Sitophilus zeamais 10.21 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks at 3 ppm after 3 days by flour disk bioassay Sitophilus zeamais 3.53 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as mortality at 1000 ppm after 3 days by flour disk bioassay (Rvb = 0%) Tribolium castaneum 14.0 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as mortality at 300 ppm after 3 days by flour disk bioassay (Rvb = 0%) Tribolium castaneum 6.0 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as mortality at 100 ppm after 3 days by flour disk bioassay (Rvb = 0%) Tribolium castaneum 2.0 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as mortality at 30 ppm after 3 days by flour disk bioassay (Rvb = 0%) Tribolium castaneum 0.0 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as mortality at 10 ppm after 3 days by flour disk bioassay (Rvb = 0%) Tribolium castaneum 0.0 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as mortality at 3 ppm after 3 days by flour disk bioassay (Rvb = 0%) Tribolium castaneum 0.0 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as mortality at 1000 ppm after 3 days by flour disk bioassay (Rvb = 0%) Sitophilus zeamais 10.0 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as mortality at 300 ppm after 3 days by flour disk bioassay (Rvb = 0%) Sitophilus zeamais 4.0 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as mortality at 100 ppm after 3 days by flour disk bioassay (Rvb = 0%) Sitophilus zeamais 0.0 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as mortality at 30 ppm after 3 days by flour disk bioassay (Rvb = 0%) Sitophilus zeamais 0.0 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as mortality at 10 ppm after 3 days by flour disk bioassay (Rvb = 0%) Sitophilus zeamais 0.0 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as mortality at 3 ppm after 3 days by flour disk bioassay (Rvb = 0%) Sitophilus zeamais 0.0 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as food utilization rate at 1000 ppm after 3 days by flour disk bioassay (Rvb = 20.59 +/-1.47%) Tribolium castaneum 7.81 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as food utilization rate at 300 ppm after 3 days by flour disk bioassay (Rvb = 20.59 +/-1.47%) Tribolium castaneum 10.03 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as food utilization rate at 100 ppm after 3 days by flour disk bioassay (Rvb = 20.59 +/-1.47%) Tribolium castaneum 13.72 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as food utilization rate at 30 ppm after 3 days by flour disk bioassay (Rvb = 20.59 +/-1.47%) Tribolium castaneum 15.12 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as food utilization rate at 10 ppm after 3 days by flour disk bioassay (Rvb = 20.59 +/-1.47%) Tribolium castaneum 19.41 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as food utilization rate at 3 ppm after 3 days by flour disk bioassay (Rvb = 20.59 +/-1.47%) Tribolium castaneum 20.25 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as food utilization rate at 1000 ppm after 3 days by flour disk bioassay (Rvb = 11.09 +/-1.12%) Sitophilus zeamais 4.21 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as food utilization rate at 300 ppm after 3 days by flour disk bioassay (Rvb = 11.09 +/-1.12%) Sitophilus zeamais 6.81 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as food utilization rate at 100 ppm after 3 days by flour disk bioassay (Rvb = 11.09 +/-1.12%) Sitophilus zeamais 8.37 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as food utilization rate at 30 ppm after 3 days by flour disk bioassay (Rvb = 11.09 +/-1.12%) Sitophilus zeamais 10.34 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as food utilization rate at 10 ppm after 3 days by flour disk bioassay (Rvb = 11.09 +/-1.12%) Sitophilus zeamais 10.67 %
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as food utilization rate at 3 ppm after 3 days by flour disk bioassay (Rvb = 11.09 +/-1.12%) Sitophilus zeamais 10.98 %
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as relative food consumption rate at 1000 ppm after 3 days by flour disk bioassay (Rvb = 143.22 +/-4.32 ug/mg/day) Tribolium castaneum 15.72 ug/mg/day
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as relative food consumption rate at 300 ppm after 3 days by flour disk bioassay (Rvb = 143.22 +/-4.32 ug/mg/day) Tribolium castaneum 31.56 ug/mg/day
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as relative food consumption rate at 100 ppm after 3 days by flour disk bioassay (Rvb = 143.22 +/-4.32 ug/mg/day) Tribolium castaneum 61.88 ug/mg/day
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as relative food consumption rate at 30 ppm after 3 days by flour disk bioassay (Rvb = 143.22 +/-4.32 ug/mg/day) Tribolium castaneum 101.27 ug/mg/day
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as relative food consumption rate at 10 ppm after 3 days by flour disk bioassay (Rvb = 143.22 +/-4.32 ug/mg/day) Tribolium castaneum 124.71 ug/mg/day
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as relative food consumption rate at 3 ppm after 3 days by flour disk bioassay (Rvb = 143.22 +/-4.32 ug/mg/day) Tribolium castaneum 137.89 ug/mg/day
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as relative food consumption rate at 1000 ppm after 3 days by flour disk bioassay (Rvb = 122.72 +/-4.32 ug/mg/day) Sitophilus zeamais 18.31 ug/mg/day
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as relative food consumption rate at 300 ppm after 3 days by flour disk bioassay (Rvb = 122.72 +/-4.32 ug/mg/day) Sitophilus zeamais 45.13 ug/mg/day
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as relative food consumption rate at 100 ppm after 3 days by flour disk bioassay (Rvb = 122.72 +/-4.32 ug/mg/day) Sitophilus zeamais 59.65 ug/mg/day
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as relative food consumption rate at 30 ppm after 3 days by flour disk bioassay (Rvb = 122.72 +/-4.32 ug/mg/day) Sitophilus zeamais 92.84 ug/mg/day
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as relative food consumption rate at 10 ppm after 3 days by flour disk bioassay (Rvb = 122.72 +/-4.32 ug/mg/day) Sitophilus zeamais 112.77 ug/mg/day
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as relative food consumption rate at 3 ppm after 3 days by flour disk bioassay (Rvb = 122.72 +/-4.32 ug/mg/day) Sitophilus zeamais 120.9 ug/mg/day
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as relative growth rate at 1000 ppm after 3 days by flour disk bioassay (Rvb = 29.49 +/-1.35 ug/mg/day) Tribolium castaneum 1.23 ug/mg/day
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as relative growth rate at 300 ppm after 3 days by flour disk bioassay (Rvb = 29.49 +/-1.35 ug/mg/day) Tribolium castaneum 3.17 ug/mg/day
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as relative growth rate at 100 ppm after 3 days by flour disk bioassay (Rvb = 29.49 +/-1.35 ug/mg/day) Tribolium castaneum 8.49 ug/mg/day
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as relative growth rate at 30 ppm after 3 days by flour disk bioassay (Rvb = 29.49 +/-1.35 ug/mg/day) Tribolium castaneum 15.31 ug/mg/day
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as relative growth rate at 10 ppm after 3 days by flour disk bioassay (Rvb = 29.49 +/-1.35 ug/mg/day) Tribolium castaneum 24.21 ug/mg/day
Feeding deterrent activity against adult Tribolium castaneum (red flour beetle) on compound pre-treated wheat flour disks assessed as relative growth rate at 3 ppm after 3 days by flour disk bioassay (Rvb = 29.49 +/-1.35 ug/mg/day) Tribolium castaneum 27.92 ug/mg/day
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as relative growth rate at 1000 ppm after 3 days by flour disk bioassay (Rvb = 13.61 +/-1.13 ug/mg/day) Sitophilus zeamais 0.77 ug/mg/day
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as relative growth rate at 300 ppm after 3 days by flour disk bioassay (Rvb = 13.61 +/-1.13 ug/mg/day) Sitophilus zeamais 3.07 ug/mg/day
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as relative growth rate at 100 ppm after 3 days by flour disk bioassay (Rvb = 13.61 +/-1.13 ug/mg/day) Sitophilus zeamais 4.99 ug/mg/day
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as relative growth rate at 10 ppm after 3 days by flour disk bioassay (Rvb = 13.61 +/-1.13 ug/mg/day) Sitophilus zeamais 12.03 ug/mg/day
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as relative growth rate at 30 ppm after 3 days by flour disk bioassay (Rvb = 13.61 +/-1.13 ug/mg/day) Sitophilus zeamais 9.6 ug/mg/day
Feeding deterrent activity against adult Sitophilus zeamais on compound pretreated wheat flour disks assessed as relative growth rate at 3 ppm after 3 days by flour disk bioassay (Rvb = 13.61 +/-1.13 ug/mg/day) Sitophilus zeamais 13.27 ug/mg/day
Inhibition of AChE (unknown origin) at 10 mg/ml after 20 min by TLC bioautographic assay Homo sapiens None
Inhibition of AChE (unknown origin) using acetylthiocholine iodide as substrate incubated for 20 min prior to substrate addition measured after 20 min by Ellman's method Homo sapiens 8.6 ug.mL-1
Inhibition of AChE (unknown origin) using acetylthiocholine iodide as substrate at 0.1 mg/ml incubated for 20 min prior to substrate addition measured after 20 min by Ellman's method Homo sapiens 91.3 %

Cross References

Resources Reference
ChEMBL CHEMBL21396
FDA SRS 4E1KLC380B
PubChem 6760
SureChEMBL SCHEMBL893654
ZINC ZINC00035525
CONTENTS