N,N'-(3,3'-(but-2-yne-1,4-diyl)bis(1-((6-chloropyridin-3-yl)methyl)imidazolidin-3-yl-2-ylidene))dinitramide

ID: ALA2286697

PubChem CID: 76334581

Max Phase: Preclinical

Molecular Formula: C22H22Cl2N10O4

Molecular Weight: 561.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])/N=C1\N(CC#CCN2CCN(Cc3ccc(Cl)nc3)/C2=N/[N+](=O)[O-])CCN1Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C22H22Cl2N10O4/c23-19-5-3-17(13-25-19)15-31-11-9-29(21(31)27-33(35)36)7-1-2-8-30-10-12-32(22(30)28-34(37)38)16-18-4-6-20(24)26-14-18/h3-6,13-14H,7-12,15-16H2/b27-21+,28-22+

Standard InChI Key:  MNCNHZZVQCNZGC-GPAWKIAZSA-N

Molfile:  

     RDKit          2D

 38 41  0  0  0  0  0  0  0  0999 V2000
   20.1287  -14.2763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8057  -14.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5748  -15.5262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7569  -15.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4849  -14.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5757  -14.4679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7238  -13.6643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4957  -13.3895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1037  -13.1331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9751  -16.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7922  -16.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2057  -15.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0221  -15.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4239  -16.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0033  -16.9688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1883  -16.9569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2410  -16.2730    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.9992  -12.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0189  -10.2246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8343  -10.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2413   -9.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8339   -8.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0153   -8.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6121   -9.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0584   -9.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5511  -10.1737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3160  -10.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9863  -11.4237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6388  -10.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3695  -10.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5439  -11.2225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3898  -12.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0066  -12.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6166  -12.2953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7949   -9.5254    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.7132  -12.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4186  -13.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1258  -13.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  1  2  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
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 21 25  1  0
 25 26  1  0
 27 28  1  0
 26 27  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
 24 35  1  0
 28 18  1  0
 18 36  1  0
 36 37  3  0
 37 38  1  0
 38  1  1  0
M  CHG  4   7   1   9  -1  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2286697

   (NE)-N-[1-[(6-chloropyridin-3-yl)methyl]-3-[4-[(2E)-3-[(6-chloropyridin-3-yl)methyl]-2-nitroiminoimidazolidin-1-yl]but-2-ynyl]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: 561.39

Molecular Weight (Monoisotopic): 560.1203

AlogP: 1.82

#Rotatable Bonds: 8

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: 0.12

CX LogP: 1.89

CX LogD: 1.89

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.20

Np Likeness Score: -0.61

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]

Source

Source(1):

• Scientific Literature