ID: ALA1593566

Max Phase: Unknown

Molecular Formula: C22H19Br2NO3

Molecular Weight: 505.21

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC1(C)[C@H](C(=O)O[C@H](C#N)c2cccc(Oc3ccccc3)c2)[C@@H]1C=C(Br)Br

Standard 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

Standard InChI Key:  OWZREIFADZCYQD-NSHGMRRFSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 505.21

Molecular Weight (Monoisotopic): 502.9732

AlogP: 6.49

#Rotatable Bonds: 6

Polar Surface Area: 59.32

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.65

CX Basic pKa:

CX LogP: 5.74

CX LogD: 5.74

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: 0.41

References

1. PubChem BioAssay data set, 

2. PubChem BioAssay data set, 

3. Matsuya Y, Ihara D, Fukuchi M, Honma D, Itoh K, Tabuchi A, Nemoto H, Tsuda M..  (2012)  Synthesis and biological evaluation of pyrethroid insecticide-derivatives as a chemical inducer for Bdnf mRNA expression in neurons.,  20  (8): [PMID:22429507] [10.1016/j.bmc.2012.02.048]

4. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

5. Kumar R, Sharma P, Shard A, Tewary DK, Nadda G, Sinha AK.  (2012)  Chalcones as promising pesticidal agents against diamondback moth (Plutella xylostella): microwave-assisted synthesis and structureactivity relationship,  21  (6): [10.1007/s00044-011-9602-8]

6. Zheng Z, Wang J, Zhang D, Guan X, Gao S, Chen Z, Zou X..  (2011)  Design, synthesis, and insecticidal activities of novel monohalovinylated pyrethroids.,  59  (4): [PMID:21275401] [10.1021/jf103908d]

7. Bonafos R, Vigues V, Serrano E, Auger P..  (2008)  Resistance monitoring to deltamethrin and chlorpyriphos-ethyl in 13 populations of Typhlodromus pyri Scheuten (Acari: Phytoseiidae) from vineyards in the southwest of France,  27  (3): [10.1016/j.cropro.2007.07.005]

8. Suri KS, Singh G..  (2011)  Insecticide-induced resurgence of the whitebacked planthopper Sogatella furcifera (Horvath) (Hemiptera: Delphacidae) on rice varieties with different levels of resistance,  30  (2): [10.1016/j.cropro.2010.11.008]

9. Campos MR, Picanço MC, Martins JC, Tomaz AC, Guedes RNC..  (2011)  Insecticide selectivity and behavioral response of the earwig Doru luteipes,  30  (12): [10.1016/j.cropro.2011.08.013]

10. Achaleke J, Martin T, Ghogomu RT, Vaissayre M, Brévault T..  (2009)  Esterase-mediated resistance to pyrethroids in field populations of Helicoverpa armigera (Lepidoptera: Noctuidae) from Central Africa.,  65  (10): [PMID:19548293] [10.1002/ps.1807]

11. Feng Y, Wu Q, Wang S, Chang X, Xie W, Xu B, Zhang Y..  (2010)  Cross-resistance study and biochemical mechanisms of thiamethoxam resistance in B-biotype Bemisia tabaci (Hemiptera: Aleyrodidae).,  66  (3): [PMID:19937914] [10.1002/ps.1877]

12. Akmoutsou P, Mademtzoglou D, Nakou I, Onoufriadis A, Papadopoulou X, Kounatidis I, Frantzios G, Papadakis G, Vasiliadis K, Papadopoulos NT, Mavragani-Tsipidou P..  (2011)  Evaluation of toxicity and genotoxic effects of spinosad and deltamethrin in Drosophila melanogaster and Bactrocera oleae.,  67  (12): [PMID:21626654] [10.1002/ps.2208]

13. KANAOKA A, YAMAGUCHI R, KONNO T.  (1996)  Effect of Buprofezin on Oviposition of Brown Planthopper, Nilaparvata lugens, at Sub-lethal Dose,  21  (2): [10.1584/jpestics.21.153]

14. PubChem BioAssay data set, 

15. PubChem BioAssay data set, 

16. WHO Anatomical Therapeutic Chemical Classification, 

17. Touré S, Nirma C, Falkowski M, Dusfour I, Boulogne I, Jahn-Oyac A, Coke M, Azam D, Girod R, Moriou C, Odonne G, Stien D, Houël E, Eparvier V..  (2017)  Aedes aegypti Larvicidal Sesquiterpene Alkaloids from Maytenus oblongata.,  80  (2): [PMID:28186749] [10.1021/acs.jnatprod.6b00850]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification