Synonyms
UNII 03L9OT429T
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 JUVIOZPCNVVQFO-HBGVWJBISA-N
Smiles COc1cc2OC[C@H]3Oc4c5C[C@@H](Oc5ccc4C(=O)[C@H]3c2cc1OC)C(=C)C
InChI
InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H22O6
Molecular Weight 394.42
AlogP 3.93
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 3.0
Polar Surface Area 63.22
Molecular species None
Aromatic Rings 2.0
Heavy Atoms 29.0
Assay Description Organism Bioactivity Reference
Inhibition of F1 generation emergence in adult Callosobruchus maculatus grown on compound pre-treated cowpea seeds assessed as reduction in adult emergence at 10 to 500 ppm measured over 2 weeks from start of F1 emergence Callosobruchus maculatus None
Inhibition of oviposition in adult Callosobruchus maculatus grown on compound pre-treated cowpea seeds assessed as reduction in number of eggs at 10 to 500 ppm measured after 72 hr Callosobruchus maculatus None
Insecticidal activity against adult Callosobruchus maculatus assessed reduction mean survival fraction measured 72 hr post dose (Rvb = 4.4 +/- 0.31 mean survival fraction) Callosobruchus maculatus 10.0 ppm
Insecticidal activity against adult Callosobruchus maculatus assessed mean survival fraction ratio at 10 ppm measured 72 hr post dose (Rvb = 4.4 +/- 0.31 mean survival fraction) Callosobruchus maculatus 1.0
Insecticidal activity against adult Callosobruchus maculatus assessed mean survival fraction ratio at 100 ppm measured 72 hr post dose (Rvb = 4.4 +/- 0.31 mean survival fraction) Callosobruchus maculatus 0.7
Insecticidal activity against adult Callosobruchus maculatus assessed mean survival fraction ratio at 500 ppm measured 72 hr post dose (Rvb = 4.4 +/- 0.31 mean survival fraction) Callosobruchus maculatus 0.4
Inhibition of adult Drosophila melanogaster AChE by colorimetric method Drosophila melanogaster None
Relative toxicity, LD50 for rotenone Drosophila melanogaster adulticidal activity to LD50 for compound Drosophila melanogaster adulticidal activity Drosophila melanogaster 1.0
Insecticidal activity against 5 to 7 days old adult Drosophila melanogaster assessed as mortality measured as inability to move compound treated in diet at 25 degC and >90% RH treated for 8 days Drosophila melanogaster 3.68 ug
Relative toxicity, LC50 for rotenone Drosophila melanogaster larvicidal activity to LC50 for compound Drosophila melanogaster larvicidal activity Drosophila melanogaster 1.0
Insecticidal activity against Drosophila melanogaster larvae assessed as mortality compound treated in diet at 25 degC and >90% RH treated for 8 days Drosophila melanogaster 20000.0 nM
Inhibition of Drosophila melanogaster AChE by colorimetric method Drosophila melanogaster None
Adulticidal activity against adult Drosophila melanogaster (males/females 1:1 ratio) assessed as mortality measured after 3 hr Drosophila melanogaster 3.68 ug
Cytotoxicity against Spodoptera litura cells assessed as growth inhibition at 20 mg/L after 24 hr by MTT assay relative to control Spodoptera litura 74.4 %
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality measured 48 hr after compound treatment Brontispa longissima 1.61 ug.mL-1
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality measured 24 hr after compound treatment Brontispa longissima 5.32 ug.mL-1
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality at 5 ug/ml measured 72 hr after compound treatment Brontispa longissima 76.67 %
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality at 5 ug/ml measured 48 hr after compound treatment Brontispa longissima 73.33 %
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality at 5 ug/ml measured 24 hr after compound treatment Brontispa longissima 66.67 %
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality at 5 ug/ml measured 12 hr after compound treatment Brontispa longissima 60.0 %
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality at 10 ug/ml measured 72 hr after compound treatment Brontispa longissima 90.0 %
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality at 10 ug/ml measured 48 hr after compound treatment Brontispa longissima 90.0 %
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality at 10 ug/ml measured 24 hr after compound treatment Brontispa longissima 90.0 %
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality at 10 ug/ml measured 12 hr after compound treatment Brontispa longissima 80.0 %
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality at 50 ug/ml measured 72 hr after compound treatment Brontispa longissima 100.0 %
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality at 50 ug/ml measured 48 hr after compound treatment Brontispa longissima 96.67 %
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality at 50 ug/ml measured 24 hr after compound treatment Brontispa longissima 86.67 %
Insecticidal activity against Brontispa longissima fifth-instar larvae fed on compound pre-treated Cocos nucifera L. leaves assessed as insect mortality at 50 ug/ml measured 12 hr after compound treatment Brontispa longissima 86.67 %
Antifeedant activity against Spodoptera litura in compound treated cork borer from fresh sweet potato leaves by Choice Leaf-Disk Bioassay Spodoptera litura 6.82 Antifeedant activity against Spodoptera litura in compound treated cork borer from fresh sweet potato leaves by Choice Leaf-Disk Bioassay Spodoptera litura 1.5 10'-7mol/cm2
Inhibition of Bos taurus (beef) heart NAD1 Bos taurus 4.4 nM
Antifeedant activity against Diaprepes abbreviatus in compound treated Citrus paradisi MacFad (Rutaceae) potted plants assessed as reduction in leaf consumption measured under 12 hr sunlight exposure at 5.6 ml/l by No-choice tests Diaprepes abbreviatus None
Antifeedant activity against Diaprepes abbreviatus in compound treated Citrus paradisi MacFad (Rutaceae) potted plants assessed as reduction in leaf consumption measured under 8 hr sunlight exposure at 5.6 ml/l by No-choice tests Diaprepes abbreviatus None
Antifeedant activity against Diaprepes abbreviatus in compound treated Citrus paradisi MacFad (Rutaceae) potted plants assessed as reduction in leaf consumption measured under 4 hr sunlight exposure at 5.6 ml/l by No-choice tests Diaprepes abbreviatus None
Antifeedant activity against Diaprepes abbreviatus in compound treated healthy romaine lettuce plants assessed as area consumed from leaf disk at 48 g/l by No-choice tests (2.51 +/- 0.2 cm'2) Diaprepes abbreviatus 2.42 cm2
Antifeedant activity against Diaprepes abbreviatus in compound treated healthy romaine lettuce plants assessed as area consumed from leaf disk at 48 g/l by choice tests (1.47 +/- 0.1 cm'2) Diaprepes abbreviatus 0.24 cm2
Antifeedant activity against Schistocerca americana in compound treated healthy romaine lettuce plants assessed as area consumed from leaf disk at 48 g/l by choice tests (1.88 +/- 0.2 cm'2) Schistocerca americana 1.64 cm2
Adulticidal activity against Drosophila melanogaster larvae assessed as mortality measured per adult Drosophila melanogaster 3.68 ug
Larvicidal activity against Drosophila melanogaster larvae assessed as mortality administered through diet after 8 days Drosophila melanogaster 20000.0 nM
Disruption of mitochondria in insecticide-susceptible Drosophila melanogaster Hikone-R assessed as increase in cytochrome c release from mitochondria to cytosol at 1 mM by western blot analysis Drosophila melanogaster None
Disruption of mitochondria in insecticide-susceptible Drosophila melanogaster Canton-S assessed as increase in cytochrome c release from mitochondria to cytosol at 1 mM by western blot analysis Drosophila melanogaster None
Antifeedant activity against third-instar Spodoptera litura assessed per cm2 leaf disk Spodoptera litura 59.1 ug
Inhibition of Escherichia coli GR19N NDH2 assessed as deaminoNADH-DB reductase activity at 100 uM relative to control Escherichia coli 70.0 %
Inhibition of Escherichia coli GR19N NDH1 assessed as deaminoNADH-DB reductase activity Escherichia coli 12589.25 nM
Inhibition of Solanum tuberosum (potato) inner mitochondrial membrane NDH2 assessed as deaminoNADH-DB reductase activity at 100 uM relative to control Solanum tuberosum None
Inhibition of Solanum tuberosum (potato) submitochondrial particle NDH1 assessed as deaminoNADH-DB reductase activity Solanum tuberosum 5011.87 nM
Inhibition of Bos taurus (bovine) heart submitochondrial particle NDH1 assessed as NADH-DB reductase activity Bos taurus 25.7 nM
Inhibition of Bos taurus (bovine) heart mitochondrial NADPH oxidase activity assessed per mg protein Bos taurus 0.17 nM
Cytotoxicity against Spodoptera frugiperda (fall armyworm) Sf9 cells at 1 to 10 uM after 72 hr by trypan blue dye exclusion test Spodoptera frugiperda None
Reduction of ATP level in Spodoptera frugiperda (fall armyworm) Sf9 cells at 0.1 to 10 uM after 4 hr by luminescent cell viability assay Spodoptera frugiperda None

Cross References

Resources Reference
ChEMBL CHEMBL429023
FDA SRS 03L9OT429T
SureChEMBL SCHEMBL42253
ZINC ZINC03860715