ID: ALA373204

Max Phase: Unknown

Molecular Formula: C22H19Cl2NO3

Molecular Weight: 416.30

Molecule Type: Small molecule

Representations

Synonyms (8): .alpha.-cypermethrin | .zeta.-cypermethrin | Alpha-Cypermethrin | Alphacypermethrin | Cypermethrin, .zeta.- | Dudu alpha | NSC-760420 | WL85871
Synonyms from Alternative Forms(8):

Canonical SMILES:  CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1

Standard InChI:  InChI=1S/C22H19Cl2NO3/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

Standard InChI Key:  KAATUXNTWXVJKI-UHFFFAOYSA-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: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 416.30

Molecular Weight (Monoisotopic): 415.0742

AlogP: 6.18

#Rotatable Bonds: 6

Polar Surface Area: 59.32

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.65

CX Basic pKa:

CX LogP: 5.44

CX LogD: 5.44

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: 0.25

References

1. Lahm GP, Selby TP, Freudenberger JH, Stevenson TM, Myers BJ, Seburyamo G, Smith BK, Flexner L, Clark CE, Cordova D..  (2005)  Insecticidal anthranilic diamides: a new class of potent ryanodine receptor activators.,  15  (22): [PMID:16165355] [10.1016/j.bmcl.2005.08.034]

2. Zhang L, Yu J, Pan H, Hu P, Hao Y, Cai W, Zhu H, Yu AD, Xie X, Ma D, Yuan J..  (2007)  Small molecule regulators of autophagy identified by an image-based high-throughput screen.,  104  (48): [PMID:18024584] [10.1073/pnas.0709695104]

3. Alali FQ, Liu XX, McLaughlin JL..  (1999)  Annonaceous acetogenins: recent progress.,  62  (3): [PMID:10096871] [10.1021/np980406d]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

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

7. PubChem BioAssay data set, 

8. Chae SH, Kim SI, Yeon SH, Lee SW, Ahn YJ..  (2011)  Adulticidal activity of phthalides identified in Cnidium officinale rhizome to B- and Q-biotypes of Bemisia tabaci.,  59  (15): [PMID:21728333] [10.1021/jf201927t]

9. Aggarwal N, Kumar R, Srivastva C, Dureja P, Khurana JM..  (2010)  Synthesis of nalidixic acid based hydrazones as novel pesticides.,  58  (5): [PMID:20131903] [10.1021/jf904144e]

10. 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]

11. Cudworth DP, Hegde VB, Yap MC, Guenthenspberger KA, Hamilton CT, Pechacek JT, Johnson PL, Bis SJ, Tisdell FE, Dripps JE, Bruce TJ, Dintenfass LP, Gifford JM, Karr LL, Kempe MK, McCormick DC, Schoonover JR..  (2007)  Structure-activity relationship development of dihaloaryl triazole compounds as insecticides and acaricides. 1. Phenyl thiophen-2-yl triazoles.,  55  (18): [PMID:17696361] [10.1021/jf071498s]

12. Wang Y, Yu R, Zhao X, Chen L, Wu C, Cang T, Wang Q..  (2012)  Susceptibility of adult Trichogramma nubilale (Hymenoptera: Trichogrammatidae) to selected insecticides with different modes of action,  34  [10.1016/j.cropro.2011.12.007]

13. Khurana JM, Magoo D, Aggarwal K, Aggarwal N, Kumar R, Srivastava C..  (2012)  Synthesis of novel 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-thiones and evaluation of their biocidal effects.,  58  [PMID:23153816] [10.1016/j.ejmech.2012.10.025]

14. 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]

15. Wang Z, Yao M, Wu Y..  (2009)  Cross-resistance, inheritance and biochemical mechanisms of imidacloprid resistance in B-biotype Bemisia tabaci.,  65  (11): [PMID:19562662] [10.1002/ps.1808]

16. Hopkins BW, Pietrantonio PV..  (2010)  Differential efficacy of three commonly used pyrethroids against laboratory and field-collected larvae and adults of Helicoverpa zea (Lepidoptera: Noctuidae) and significance for pyrethroid resistance management.,  66  (2): [PMID:19757481] [10.1002/ps.1847]

17. Carletto J, Martin T, Vanlerberghe-Masutti F, Brévault T..  (2010)  Insecticide resistance traits differ among and within host races in Aphis gossypii.,  66  (3): [PMID:19908228] [10.1002/ps.1874]

18. Saito S, Sakamoto N, Umeda K.  (2005)  Effects of Pyridalyl, a Novel Insecticidal Agent, on Cultured Sf9 Cells,  30  (1): [10.1584/jpestics.30.17]

19. PubChem BioAssay data set, 

20. PubChem BioAssay data set, 

21. PubChem BioAssay data set, 

22. PubChem BioAssay data set, 

23. WHO Anatomical Therapeutic Chemical Classification, 

24. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

25. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(6):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data