N',N-(3,3'-(propane-1,3-diyl)bis(1-((6-chloropyridin-3-yl)methyl)imidazolidin-3-yl-2-ylidene))dinitramide

ID: ALA2286701

PubChem CID: 20770748

Max Phase: Preclinical

Molecular Formula: C21H24Cl2N10O4

Molecular Weight: 551.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])/N=C1/N(CCCN2CCN(Cc3ccc(Cl)nc3)/C2=N/[N+](=O)[O-])CCN1Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C21H24Cl2N10O4/c22-18-4-2-16(12-24-18)14-30-10-8-28(20(30)26-32(34)35)6-1-7-29-9-11-31(21(29)27-33(36)37)15-17-3-5-19(23)25-13-17/h2-5,12-13H,1,6-11,14-15H2/b26-20-,27-21+

Standard InChI Key:  IMVHHLBCVJNKCV-QRNPONQASA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   17.1946   -5.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4396   -6.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2640   -6.4373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5283   -5.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8663   -5.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9464   -7.0895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2725   -7.8473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0941   -7.9471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7815   -8.5119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6884   -7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5133   -7.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9356   -7.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7597   -7.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1610   -7.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7320   -6.3931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9093   -6.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9858   -7.0879    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.8934   -1.9674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7162   -1.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1052   -1.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6724   -0.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8465   -0.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4613   -1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6368   -1.2995    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.9299   -1.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4065   -1.8684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1383   -2.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7998   -3.1460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4732   -2.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2278   -1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3503   -2.8970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1676   -3.7015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7718   -4.2657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3783   -3.9493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7896   -3.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4989   -4.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4887   -5.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  2  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  3 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 23 24  1  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 26  1  0
 27 31  2  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 28 35  1  0
 35 36  1  0
 36 37  1  0
 37  1  1  0
M  CHG  4   7   1   9  -1  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2286701

   (NZ)-N-[1-[(6-chloropyridin-3-yl)methyl]-3-[3-[(2E)-3-[(6-chloropyridin-3-yl)methyl]-2-nitroiminoimidazolidin-1-yl]propyl]imidazolidin-2-ylidene]nitramide

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: 551.40

Molecular Weight (Monoisotopic): 550.1359

AlogP: 2.20

#Rotatable Bonds: 10

Polar Surface Area: 149.74

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 0.17

CX LogP: 1.48

CX LogD: 1.48

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.24

Np Likeness Score: -0.69

References

1. KAGABU S, IWAYA K, KONISHI H, SAKAI A, ITAZU Y, KIRIYAMA K, NISHIMURA K.  (2002)  Synthesis of Alkylene-Tethered Bis-Imidacloprid Derivatives as Highly Insecticidal and Nerve-Exciting Agents with Potent Affinity to [3H] Imidacloprid-Binding Sites on Nicotinic Acetylcholine Receptor,  27  (3): [10.1584/jpestics.27.249]

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

Source

Source(1):

• Scientific Literature