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name Structure Reference Source Properties Activities Metabolism

(R)-cyano(3-phenoxyphenyl)methyl (1S,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate

AlkaPlorer ID: AK105594

Synonym: None

IUPAC Name: [(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate

Structure

SMILES: CC1(C)[C@H](C(=O)O[C@H](C#N)C2=CC=CC(OC3=CC=CC=C3)=C2)[C@@H]1C=C(Br)Br

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InChI: InChI=1S/C22H19Br2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18+,20-/m0/s1

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InChIKey: OWZREIFADZCYQD-NSHGMRRFSA-N

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Reference

PubChem CID: 40585

CAS: 52820-00-5

NPASS: NPC251849

Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 505.206

TPSA？: 59.32000000000001

MolLogP？: 6.490180000000004

Number of H-Donors: 0

Number of H-Acceptors: 4

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Aedes aegypti Aedes aegypti mortality 26.0 % 10.1021/acs.jnatprod.6b00850
Aedes aegypti Aedes aegypti mortality 100.0 % 10.1021/acs.jnatprod.6b00850
Bactrocera oleae Bactrocera oleae LC50 0.176 ug.mL-1 10.1002/ps.2208
Bactrocera oleae Bactrocera oleae LC50 0.344 ug.mL-1 10.1002/ps.2208
Bactrocera oleae Bactrocera oleae LC50 0.414 ug.mL-1 10.1002/ps.2208
Bactrocera oleae Bactrocera oleae LC50 2.851 ug.mL-1 10.1002/ps.2208
Bactrocera oleae Bactrocera oleae LC90 0.161 mg/L 10.1002/ps.2208
Bactrocera oleae Bactrocera oleae LC90 0.398 mg/L 10.1002/ps.2208
Bactrocera oleae Bactrocera oleae LC90 1.002 mg/L 10.1002/ps.2208
Bactrocera oleae Bactrocera oleae LC90 6.033 mg/L 10.1002/ps.2208
Bemisia tabaci Bemisia tabaci LC50 701.0 ug.mL-1 10.1002/ps.1877
Bemisia tabaci Bemisia tabaci LC50 810.0 ug.mL-1 10.1002/ps.1877
Bemisia tabaci Bemisia tabaci RatioLC50 1.16 None 10.1002/ps.1877
Culex pipiens pallens Culex pipiens pallens LC50 0.0012 ug.mL-1 10.1021/jf103908d
Culex pipiens pallens Culex pipiens pallens LC95 0.0033 mg/L 10.1021/jf103908d
Culex pipiens pallens Culex pipiens pallens RatioLC50 883.0 None 10.1021/jf103908d
Doru Doru LC50 22.6 ug.mL-1 10.1016/j.cropro.2011.08.013
Doru Doru Ratio 33000.0 None 10.1016/j.cropro.2011.08.013
Drosophila melanogaster Drosophila melanogaster Activity nan None 10.1002/ps.2208
Drosophila melanogaster Drosophila melanogaster LC50 4.817 ug.mL-1 10.1002/ps.2208
Drosophila melanogaster Drosophila melanogaster LC50 4.957 ug.mL-1 10.1002/ps.2208
Drosophila melanogaster Drosophila melanogaster LC50 7.24 ug.mL-1 10.1002/ps.2208
Drosophila melanogaster Drosophila melanogaster LC50 8.034 ug.mL-1 10.1002/ps.2208
Drosophila melanogaster Drosophila melanogaster LC50 17.09 ug.mL-1 10.1002/ps.2208
Drosophila melanogaster Drosophila melanogaster LC90 10.35 mg/L 10.1002/ps.2208
Drosophila melanogaster Drosophila melanogaster LC90 13.6 mg/L 10.1002/ps.2208
Drosophila melanogaster Drosophila melanogaster LC90 14.59 mg/L 10.1002/ps.2208
Drosophila melanogaster Drosophila melanogaster LC90 17.41 mg/L 10.1002/ps.2208
Drosophila melanogaster Drosophila melanogaster LC90 31.68 mg/L 10.1002/ps.2208
Helicoverpa armigera Helicoverpa armigera LD50 0.05 microgAi/g 10.1002/ps.1807
Helicoverpa armigera Helicoverpa armigera LD50 3.0 microgAi/g 10.1002/ps.1807
Helicoverpa armigera Helicoverpa armigera LD50 6.7 microgAi/g 10.1002/ps.1807
Helicoverpa armigera Helicoverpa armigera LD50 15.8 microgAi/g 10.1002/ps.1807
Helicoverpa armigera Helicoverpa armigera LD50 29.5 microgAi/g 10.1002/ps.1807
Helicoverpa armigera Helicoverpa armigera LD50 37.8 microgAi/g 10.1002/ps.1807
Helicoverpa armigera Helicoverpa armigera LD50 148.6 microgAi/g 10.1002/ps.1807
Helicoverpa armigera Helicoverpa armigera Ratio 60.0 None 10.1002/ps.1807
Helicoverpa armigera Helicoverpa armigera Ratio 134.0 None 10.1002/ps.1807
Helicoverpa armigera Helicoverpa armigera Ratio 316.0 None 10.1002/ps.1807
Helicoverpa armigera Helicoverpa armigera Ratio 590.0 None 10.1002/ps.1807
Helicoverpa armigera Helicoverpa armigera Ratio 756.0 None 10.1002/ps.1807
Helicoverpa armigera Helicoverpa armigera Ratio 2972.0 None 10.1002/ps.1807
Homo sapiens Bile acid receptor FXR Potency 15848.9 nM None
Homo sapiens Glucocorticoid receptor Potency 2.8 nM None
Homo sapiens Glucocorticoid receptor Potency 44668.4 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 68589.6 nM None
Homo sapiens Nuclear factor NF-kappa-B p105 subunit Potency 39810.7 nM None
Homo sapiens Peroxisome proliferator-activated receptor gamma Potency 28183.8 nM None
Homo sapiens Retinoid X receptor alpha Potency 39810.7 nM None
Homo sapiens Runt-related transcription factor 1/Core-binding factor subunit beta Potency 22387.2 nM None
Homo sapiens Thyroid hormone receptor beta-1 Potency 10.0 nM None
Mythimna separata Mythimna separata LC50 0.1486 ug.mL-1 10.1021/jf103908d
Nilaparvata lugens Nilaparvata lugens Activity 92.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 94.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 98.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 101.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 102.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 105.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 107.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 109.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 110.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 112.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 113.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 114.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 116.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 120.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 124.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 125.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 128.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 131.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 133.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens Activity 136.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens mortality 0.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens mortality 2.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens mortality 4.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens mortality 9.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens mortality 40.0 % 10.1584/jpestics.21.153
Nilaparvata lugens Nilaparvata lugens mortality 100.0 % 10.1584/jpestics.21.153
Oryza sativa Oryza sativa Activity 2.95 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 3.73 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 4.21 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 4.62 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 5.42 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 6.92 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 7.78 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 8.0 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 10.76 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 12.0 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 12.28 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 13.8 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 14.35 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 17.08 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 19.83 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 23.89 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 35.36 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 35.62 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 38.84 mg 10.1016/j.cropro.2010.11.008
Oryza sativa Oryza sativa Activity 44.2 mg 10.1016/j.cropro.2010.11.008
Plutella xylostella Plutella xylostella LC50 6.25 ug.mL-1 10.1007/s00044-011-9602-8
Rattus norvegicus Cortical neurone Activity nan None 10.1016/j.bmc.2012.02.048
Rattus norvegicus Nuclear receptor subfamily 1 group I member 2 Potency 25118.9 nM None
Sogatella furcifera Sogatella furcifera GI 2.74 % 10.1016/j.cropro.2010.11.008
Sogatella furcifera Sogatella furcifera GI 6.77 % 10.1016/j.cropro.2010.11.008
Sogatella furcifera Sogatella furcifera Ratio 1.28 None 10.1016/j.cropro.2010.11.008
Sogatella furcifera Sogatella furcifera Ratio 1.75 None 10.1016/j.cropro.2010.11.008
Sogatella furcifera Sogatella furcifera Survival 38.89 % 10.1016/j.cropro.2010.11.008
Sogatella furcifera Sogatella furcifera Survival 78.05 % 10.1016/j.cropro.2010.11.008
Sogatella furcifera Sogatella furcifera TIME 279.12 hr 10.1016/j.cropro.2010.11.008
Sogatella furcifera Sogatella furcifera TIME 343.68 hr 10.1016/j.cropro.2010.11.008
Spodoptera frugiperda Spodoptera frugiperda LC50 0.18 ug.mL-1 10.1016/j.cropro.2011.08.013
Spodoptera frugiperda Spodoptera frugiperda LT50 44.84 min 10.1016/j.cropro.2011.08.013
Spodoptera frugiperda Spodoptera frugiperda Ratio 2.63 None 10.1016/j.cropro.2011.08.013
Spodoptera frugiperda Spodoptera frugiperda Ratio 23.2 None 10.1016/j.cropro.2011.08.013
Typhlodromus pyri Typhlodromus pyri mortality 5.3 % 10.1016/j.cropro.2007.07.005
Typhlodromus pyri Typhlodromus pyri mortality 20.6 % 10.1016/j.cropro.2007.07.005
Typhlodromus pyri Typhlodromus pyri mortality 23.6 % 10.1016/j.cropro.2007.07.005
Typhlodromus pyri Typhlodromus pyri mortality 31.2 % 10.1016/j.cropro.2007.07.005
Typhlodromus pyri Typhlodromus pyri mortality 61.8 % 10.1016/j.cropro.2007.07.005
Typhlodromus pyri Typhlodromus pyri mortality 62.9 % 10.1016/j.cropro.2007.07.005
Typhlodromus pyri Typhlodromus pyri mortality 74.0 % 10.1016/j.cropro.2007.07.005
Typhlodromus pyri Typhlodromus pyri mortality 75.0 % 10.1016/j.cropro.2007.07.005
Typhlodromus pyri Typhlodromus pyri mortality 84.3 % 10.1016/j.cropro.2007.07.005
Typhlodromus pyri Typhlodromus pyri mortality 86.1 % 10.1016/j.cropro.2007.07.005
Typhlodromus pyri Typhlodromus pyri mortality 90.2 % 10.1016/j.cropro.2007.07.005
Typhlodromus pyri Typhlodromus pyri mortality 92.0 % 10.1016/j.cropro.2007.07.005
Typhlodromus pyri Typhlodromus pyri mortality 100.0 % 10.1016/j.cropro.2007.07.005
None Molecular identity unknown Potency 11220.2 nM None
None Unchecked Potency 11220.2 nM None
None Unchecked Potency 15848.9 nM None
None Unchecked RatioLC50 152.0 None 10.1016/j.cropro.2011.08.013

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT006906 CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)c1cccc(Oc2ccccc2)c1>>C#N enzymemap_51495
AKRT006907 CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)c1cccc(Oc2ccccc2)c1>>CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O enzymemap_51495
AKRT006908 CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)c1cccc(Oc2ccccc2)c1>>O=Cc1cccc(Oc2ccccc2)c1 enzymemap_51495