Hexamethylene 1,6-bis-imadacloprid

ID: ALA2252130

Chembl Id: CHEMBL2252130

PubChem CID: 20770750

Max Phase: Preclinical

Molecular Formula: C24H30Cl2N10O4

Molecular Weight: 593.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])/N=C1/N(CCCCCCN2CCN(Cc3ccc(Cl)nc3)/C2=N/[N+](=O)[O-])CCN1Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C24H30Cl2N10O4/c25-21-7-5-19(15-27-21)17-33-13-11-31(23(33)29-35(37)38)9-3-1-2-4-10-32-12-14-34(24(32)30-36(39)40)18-20-6-8-22(26)28-16-20/h5-8,15-16H,1-4,9-14,17-18H2/b29-23-,30-24+

Standard InChI Key:  RYYRNTOJTBSRIT-UEUMJKGWSA-N

Alternative Forms

1. Parent:

   

   ALA2252130

   Hexamethylene 1,6-bis-imadacloprid

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: 593.48

Molecular Weight (Monoisotopic): 592.1829

AlogP: 3.37

#Rotatable Bonds: 13

Polar Surface Area: 149.74

Molecular Species: NEUTRAL

HBA: 6

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 0.19

CX LogP: 2.89

CX LogD: 2.89

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.15

Np Likeness Score: -0.61

References

1. Kagabu S..  (2011)  Discovery of imidacloprid and further developments from strategic molecular designs.,  59  (7): [PMID:20718435] [10.1021/jf101824y]

2. Kagabu S, Itazu Y, Nishimura K.  (2006)  1,6-Bis[1-(2-chloro-5-thiazolylmethyl)-2-nitroiminoimidazolidin-3-yl]hexane and 1,3,5-tris[1-(6-chloronicotinyl)-2-nitroiminoimidazolidin-3-ylmethyl]benzeneSynthesis and insecticidal and neuroblocking activities in American cockroaches, Periplaneta americana,  31  (2): [10.1584/jpestics.31.146]

3. Kagabu S.  (2008)  Pharmacophore of neonicotinoid insecticides,  33  (1): [10.1584/jpestics.R07-05]

Source

Source(1):

• Scientific Literature