O,O-diethyl 3,5,6-trichloropyridin-2-ylphosphonothioate

ID: ALA463210

Cas Number: 2921-88-2

PubChem CID: 2730

Product Number: C109843M, Order Now?

Max Phase: Unknown

Molecular Formula: C9H11Cl3NO3PS

Molecular Weight: 350.59

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Chloropyrifos | Dursban | ENT-27311 | NSC-755891 | chlorpyrifos|2921-88-2|Dursban|Chlorpyriphos|Lorsban|Trichlorpyrphos|Coroban|Brodan|Chlorpyrifos-ethyl|Equity|Lentrek|Pyrinex|Stipend|Chloropyrifos|Lock-On|Danusban|Killmaster|Piridane|Durmet|Terial|Dowco 179|suSCon|Dursban 4E|Bonidel|Geodinfos|Spannit|Tafaban|Radar|Zidil|Suscon blue|Suscon green|O,O-Diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate|Phosphorothioic acid, O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) ester|Dursban F|Dursban R|ChShow More⌵

Canonical SMILES:  CCOP(=S)(OCC)Oc1nc(Cl)c(Cl)cc1Cl

Standard InChI:  InChI=1S/C9H11Cl3NO3PS/c1-3-14-17(18,15-4-2)16-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3

Standard InChI Key:  SBPBAQFWLVIOKP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -0.6958   -0.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -0.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -0.1792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -0.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9833   -0.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958    1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208    1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9833    1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000    0.9833    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -1.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292    0.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750   -0.8167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    1.8958    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750    1.8958    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8292    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792    2.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  1  1  0
  5  2  2  0
  6  1  2  0
  7  6  1  0
  8  7  2  0
  9  3  2  0
 10  3  1  0
 11  3  1  0
 12  5  1  0
 13  6  1  0
 14  8  1  0
 15 11  1  0
 16 10  1  0
 17 15  1  0
 18 16  1  0
  5  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA463210

   CHLORPYRIFOS

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

Calculated Properties

Molecular Weight: 350.59

Molecular Weight (Monoisotopic): 348.9263

AlogP: 4.72

#Rotatable Bonds: 6

Polar Surface Area: 40.58

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.78

CX LogD: 4.78

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.55

Np Likeness Score: -0.30

References

1. Musilek K, Kuca K, Jun D, Dohnal V, Dolezal M, Dolezal M..  (2006)  Synthesis of the novel series of bispyridinium compounds bearing (E)-but-2-ene linker and evaluation of their reactivation activity against chlorpyrifos-inhibited acetylcholinesterase.,  16  (3): [PMID:16288867] [10.1016/j.bmcl.2005.10.059]

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

3. Tomizawa M, Kagabu S, Ohno I, Durkin KA, Casida JE..  (2008)  Potency and selectivity of trifluoroacetylimino and pyrazinoylimino nicotinic insecticides and their fit at a unique binding site niche.,  51  (14): [PMID:18570364] [10.1021/jm800191a]

4. Nomura DK, Blankman JL, Simon GM, Fujioka K, Issa RS, Ward AM, Cravatt BF, Casida JE..  (2008)  Activation of the endocannabinoid system by organophosphorus nerve agents.,  4  (6): [PMID:18438404] [10.1038/nchembio.86]

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11. Bain LJ, LeBlanc GA..  (1996)  Interaction of structurally diverse pesticides with the human MDR1 gene product P-glycoprotein.,  141  (1): [PMID:8917702] [10.1006/taap.1996.0286]

12. Lanning CL, Fine RL, Sachs CW, Rao US, Corcoran JJ, Abou-Donia MB..  (1996)  Chlorpyrifos oxon interacts with the mammalian multidrug resistance protein, P-glycoprotein.,  47  (1): [PMID:8600291] [10.1080/009841096161726]

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

14. 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]

15. Wang HY, Yang Y, Su JY, Shen JL, Gao CF, Zhu YC..  (2008)  Assessment of the impact of insecticides on Anagrus nilaparvatae (Pang et Wang) (Hymenoptera: Mymanidae), an egg parasitoid of the rice planthopper, Nilaparvata lugens (Hemiptera: Delphacidae),  27  (3): [10.1016/j.cropro.2007.08.004]

16. 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]

17. Ay R, Kara FE..  (2011)  Toxicity, inheritance of fenpyroximate resistance, and detoxification-enzyme levels in a laboratory-selected fenpyroximate-resistant strain of Tetranychus urticae Koch (Acari: Tetranychidae),  30  (6): [10.1016/j.cropro.2010.11.012]

18. 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]

19. Zhao Q, Xie R, Zhang T, Fang J, Mei X, Ning J, Tang Y..  (2011)  Homo- and hetero-dimers of inactive organophosphorous group binding at dual sites of AChE.,  21  (21): [PMID:21940169] [10.1016/j.bmcl.2011.08.098]

20. 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]

21. Abbassy MA, Abdelgaleil SAM, Belal ASH, Abdel Rasoula MAA..  (2007)  Insecticidal, antifeedant and antifungal activities of two glucosides isolated from the seeds of Simmondsia chinensis,  26  (3): [10.1016/j.indcrop.2007.04.005]

22. Morita Y, Matsumura E, Okabe T, Shibata M, Sugiura M, Ohe T, Tsujibo H, Ishida N, Inamori Y..  (2003)  Biological activity of tropolone.,  26  (10): [PMID:14519960] [10.1248/bpb.26.1487]

23. Morita Y, Matsumura E, Okabe T, Fukui T, Shibata M, Sugiura M, Ohe T, Tsujibo H, Ishida N, Inamori Y..  (2004)  Biological activity of alpha-thujaplicin, the isomer of hinokitiol.,  27  (6): [PMID:15187442] [10.1248/bpb.27.899]

24. Inamori Y, Sakagami Y, Morita Y, Shibata M, Sugiura M, Kumeda Y, Okabe T, Tsujibo H, Ishida N..  (2000)  Antifungal activity of Hinokitiol-related compounds on wood-rotting fungi and their insecticidal activities.,  23  (8): [PMID:10963310] [10.1248/bpb.23.995]

25. Gao JR, Zhu KY..  (2000)  Comparative toxicity of selected organophosphate insecticides against resistant and susceptible clones of the greenbug, Schizaphis graminum (Homoptera: aphididae).,  48  (10): [PMID:11052723] [10.1021/jf000548p]

26. Boina DR, Lewis EE, Bloomquist JR..  (2008)  Nematicidal activity of anion transport blockers against Meloidogyne incognita, Caenorhabditis elegans and Heterorhabditis bacteriophora.,  64  (6): [PMID:18407564] [10.1002/ps.1591]

27. Tiwari S, Pelz-Stelinski K, Stelinski LL..  (2011)  Effect of Candidatus Liberibacter asiaticus infection on susceptibility of Asian citrus psyllid, Diaphorina citri, to selected insecticides.,  67  (1): [PMID:20960471] [10.1002/ps.2038]

28. Xie W, Wang S, Wu Q, Feng Y, Pan H, Jiao X, Zhou L, Yang X, Fu W, Teng H, Xu B, Zhang Y..  (2011)  Induction effects of host plants on insecticide susceptibility and detoxification enzymes of Bemisia tabaci (Hemiptera: Aleyrodidae).,  67  (1): [PMID:21162148] [10.1002/ps.2037]

29. Sun D, Yang C, Ming W, Sun L, Zhang L, Zhang Q, Chai Y.  (2011)  Preparation and activity study of new organophosphate insecticide candidates,  36  (1): [10.1584/jpestics.G10-60]

30. Nyoni BN, Gorman K, Mzilahowa T, Williamson MS, Navajas M, Field LM, Bass C..  (2011)  Pyrethroid resistance in the tomato red spider mite, Tetranychus evansi, is associated with mutation of the para-type sodium channel.,  67  (8): [PMID:21432985] [10.1002/ps.2145]

31. Muralidharan K, Pasalu IC..  (2006)  Assessments of crop losses in rice ecosystems due to stem borer damage (Lepidoptera: Pyralidae),  25  (5): [10.1016/j.cropro.2005.06.007]

32. Morales-Rodriguez A, Ospina A, Peck DC..  (2010)  Variation in the laboratory susceptibility of turf-infesting white grubs (Coleoptera: Scarabaeidae) to biological, biorational and chemical control products.,  66  (1): [PMID:19742452] [10.1002/ps.1835]

33. 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]

34. Baldessari M, Trona F, Angeli G, Ioriatti C..  (2010)  Effectiveness of five insecticides for the control of adults and young stages of Cacopsylla melanoneura (Förster) (Hemiptera: Psyllidae) in a semi-field trial.,  66  (3): [PMID:19937976] [10.1002/ps.1876]

35. Sun J, Liang P, Gao X..  (2012)  Cross-resistance patterns and fitness in fufenozide-resistant diamondback moth, Plutella xylostella (Lepidoptera: Plutellidae).,  68  (2): [PMID:21858910] [10.1002/ps.2258]

36. Tiwari S, Killiny N, Mann RS, Wenninger EJ, Stelinski LL..  (2013)  Abdominal color of the Asian citrus psyllid, Diaphorina citri, is associated with susceptibility to various insecticides.,  69  (4): [PMID:23193012] [10.1002/ps.3407]

37. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

38. PubChem BioAssay data set, 

39. PubChem BioAssay data set, 

40. DrugMatrix,  [10.6019/CHEMBL3885881]

41. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

42. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

43. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

44. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(7):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• TP-search Transporter Database
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6