(3-((6-chloropyridin-3-yl)methyl)thiazolidin-2-ylidene)cyanamide

ID: ALA451432

Chembl Id: CHEMBL451432

Cas Number: 111988-49-9

PubChem CID: 115224

Product Number: T114779M

Max Phase: Preclinical

Molecular Formula: C10H9ClN4S

Molecular Weight: 252.73

Molecule Type: Small molecule

Names and Identifiers

Synonyms: thiacloprid | Thiacloprid|111988-49-9|Calypso|(Z)-thiacloprid|(3-((6-Chloro-3-pyridinyl)methyl)-2-thiazolidinylidene)cyanamide|[3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene]cyanamide|CHEMBL451432|DSV3A944A4|DTXSID7034961|CHEBI:39176|{(2Z)-3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide|[3-(6-Chloro-3-pyridinylmethyl)-2-thiazolidinylidene]cyanamide|{3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide|Cyanamide, [3-[(6-chloro-3-pyridinyl)methyl]-Show More⌵

Canonical SMILES:  N#C/N=C1\SCCN1Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C10H9ClN4S/c11-9-2-1-8(5-13-9)6-15-3-4-16-10(15)14-7-12/h1-2,5H,3-4,6H2/b14-10-

Standard InChI Key:  HOKKPVIRMVDYPB-UVTDQMKNSA-N

Alternative Forms

1. Parent:

   

   ALA451432

   THIACLOPRID

Molecule Features

Natural Product: No

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

Calculated Properties

Molecular Weight: 252.73

Molecular Weight (Monoisotopic): 252.0236

AlogP: 2.12

#Rotatable Bonds: 2

Polar Surface Area: 52.28

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 1.62

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.60

Np Likeness Score: -1.91

References

1. Tomizawa M, Talley TT, Maltby D, Durkin KA, Medzihradszky KF, Burlingame AL, Taylor P, Casida JE..  (2007)  Mapping the elusive neonicotinoid binding site.,  104  (21): [PMID:17485662] [10.1073/pnas.0703309104]

2. 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]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Sun Y, Qiao H, Ling Y, Yang S, Rui C, Pelosi P, Yang X..  (2011)  New analogues of (E)-β-farnesene with insecticidal activity and binding affinity to aphid odorant-binding proteins.,  59  (6): [PMID:21341697] [10.1021/jf104712c]

6. Ford KA, Gulevich AG, Swenson TL, Casida JE..  (2011)  Neonicotinoid insecticides: oxidative stress in planta and metallo-oxidase inhibition.,  59  (9): [PMID:21476569] [10.1021/jf200485k]

7. 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]

8. Tomizawa M, Casida JE..  (2011)  Unique neonicotinoid binding conformations conferring selective receptor interactions.,  59  (7): [PMID:21341671] [10.1021/jf1019455]

9. Zhang A, Kayser H, Maienfisch P, Casida JE..  (2000)  Insect nicotinic acetylcholine receptor: conserved neonicotinoid specificity of [(3)H]imidacloprid binding site.,  75  (3): [PMID:10936213] [10.1046/j.1471-4159.2000.751294.x]

10. Bostanian NJ, Thistlewood HA, Hardman JM, Laurin MC, Racette G..  (2009)  Effect of seven new orchard pesticides on Galendromus occidentalis in laboratory studies.,  65  (6): [PMID:19206104] [10.1002/ps.1721]

11. Tomizawa M, Lee DL, Casida JE..  (2000)  Neonicotinoid insecticides: molecular features conferring selectivity for insect versus mammalian nicotinic receptors.,  48  (12): [PMID:11312774] [10.1021/jf000873c]

12. 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]

13. Yokoyama A, Ohtsu K, Iwafune T, Nagai T, Ishihara S, Kobara Y, Horio T, Endo S.  (2009)  A useful new insecticide bioassay using first-instar larvae of a net-spinning caddisfly, Cheumatopsyche brevilineata (Trichoptera: Hydropsychidae),  34  (1): [10.1584/jpestics.G08-26]

14. KAGABU S, AZUMA A, NISHIMURA K.  (2002)  Insecticidal and Neuroblocking Activities of Thiacloprid and Its Acyclic Analogues and Their Related Cyanoguanidine Derivatives,  27  (3): [10.1584/jpestics.27.267]

15. Shi X, Jiang L, Wang H, Qiao K, Wang D, Wang K..  (2011)  Toxicities and sublethal effects of seven neonicotinoid insecticides on survival, growth and reproduction of imidacloprid-resistant cotton aphid, Aphis gossypii.,  67  (12): [PMID:21714058] [10.1002/ps.2207]

16. Guillén J, Bielza P..  (2013)  Thiamethoxam acts as a target-site synergist of spinosad in resistant strains of Frankliniella occidentalis.,  69  (2): [PMID:22847768] [10.1002/ps.3372]

17. Cutler P, Slater R, Edmunds AJ, Maienfisch P, Hall RG, Earley FG, Pitterna T, Pal S, Paul VL, Goodchild J, Blacker M, Hagmann L, Crossthwaite AJ..  (2013)  Investigating the mode of action of sulfoxaflor: a fourth-generation neonicotinoid.,  69  (5): [PMID:23112103] [10.1002/ps.3413]

18. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays