N,N'-(3,3'-(nonane-1,9-diyl)bis(1-((6-chloropyridin-3-yl)methyl)imidazolidin-3-yl-2-ylidene))dinitramide

ID: ALA2286699

PubChem CID: 20770753

Max Phase: Preclinical

Molecular Formula: C27H36Cl2N10O4

Molecular Weight: 635.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])/N=C1/N(CCCCCCCCCN2CCN(Cc3ccc(Cl)nc3)/C2=N/[N+](=O)[O-])CCN1Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C27H36Cl2N10O4/c28-24-10-8-22(18-30-24)20-36-16-14-34(26(36)32-38(40)41)12-6-4-2-1-3-5-7-13-35-15-17-37(27(35)33-39(42)43)21-23-9-11-25(29)31-19-23/h8-11,18-19H,1-7,12-17,20-21H2/b32-26-,33-27+

Standard InChI Key:  MBPRFODQNKJUMW-YUGUBMJKSA-N

Molfile:  

     RDKit          2D

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   13.5541  -30.2594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4610  -28.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.6819  -28.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3118  -19.3079    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.6049  -19.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0815  -19.8768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8133  -20.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4748  -21.1544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8426  -21.7099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4468  -22.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0533  -21.9577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   13.2612  -26.9642    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
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 12 13  1  0
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 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 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43  1  1  0
M  CHG  4   7   1   9  -1  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2286699

   (NZ)-N-[1-[(6-chloropyridin-3-yl)methyl]-3-[9-[(2E)-3-[(6-chloropyridin-3-yl)methyl]-2-nitroiminoimidazolidin-1-yl]nonyl]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: 635.56

Molecular Weight (Monoisotopic): 634.2298

AlogP: 4.54

#Rotatable Bonds: 16

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: 0.21

CX LogP: 4.22

CX LogD: 4.22

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.11

Np Likeness Score: -0.57

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