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

ID: ALA2286698

PubChem CID: 76316416

Max Phase: Preclinical

Molecular Formula: C22H24Cl2N10O4

Molecular Weight: 563.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])/N=C1\N(C/C=C/CN2CCN(Cc3ccc(Cl)nc3)/C2=N/[N+](=O)[O-])CCN1Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C22H24Cl2N10O4/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/h1-6,13-14H,7-12,15-16H2/b2-1+,27-21+,28-22+

Standard InChI Key:  BVBYGIXYMAUMRQ-MKKRFYIUSA-N

Molfile:  

     RDKit          2D

 38 41  0  0  0  0  0  0  0  0999 V2000
    6.8954  -13.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5966  -12.8332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3828  -13.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8513  -12.4008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3573  -11.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5849  -12.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6502  -13.8435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1151  -14.4611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3828  -15.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3129  -14.3088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6688  -12.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0858  -13.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6825  -13.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0989  -14.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9169  -14.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3168  -13.7801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8981  -13.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3349  -15.1998    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1818  -12.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673  -12.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870  -10.8602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6024  -10.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0094  -10.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6020   -9.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7835   -9.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3802  -10.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8266  -10.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3192  -10.8093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0841  -11.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7544  -12.0593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4069  -11.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1376  -10.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3120  -11.8581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579  -12.6606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747  -13.1978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3847  -12.9309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5630  -10.1610    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4813  -13.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  4  1  0
  2  3  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  3  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 19  1  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 23 27  1  0
 27 28  1  0
 29 30  1  0
 28 29  1  0
 30 31  1  0
 31 32  1  0
 32 28  1  0
 29 33  2  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 26 37  1  0
 30 20  1  0
 20 38  1  0
 38 19  2  0
M  CHG  4   8   1  10  -1  34   1  36  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2286698

   (NE)-N-[1-[(6-chloropyridin-3-yl)methyl]-3-[(E)-4-[(2E)-3-[(6-chloropyridin-3-yl)methyl]-2-nitroiminoimidazolidin-1-yl]but-2-enyl]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: 563.41

Molecular Weight (Monoisotopic): 562.1359

AlogP: 2.37

#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: 0.14

CX LogP: 1.95

CX LogD: 1.95

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.18

Np Likeness Score: -0.52

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