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

ID: ALA2286696

PubChem CID: 76309178

Max Phase: Preclinical

Molecular Formula: C24H30Cl2N10O5

Molecular Weight: 609.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])/N=C1/N(CCCOCCCN2CCN(Cc3ccc(Cl)nc3)/C2=N/[N+](=O)[O-])CCN1Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C24H30Cl2N10O5/c25-21-5-3-19(15-27-21)17-33-11-9-31(23(33)29-35(37)38)7-1-13-41-14-2-8-32-10-12-34(24(32)30-36(39)40)18-20-4-6-22(26)28-16-20/h3-6,15-16H,1-2,7-14,17-18H2/b29-23-,30-24+

Standard InChI Key:  AAWRCBWYNSEVTD-UEUMJKGWSA-N

Molfile:  

     RDKit          2D

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   10.9551  -19.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4718  -19.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0368  -20.7238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7238  -21.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5397  -21.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9106  -22.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7260  -22.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.9772  -20.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9857  -21.4291    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    1.7504  -15.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472  -16.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935  -16.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2862  -17.0496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0510  -17.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7214  -18.2996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3739  -17.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1046  -17.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790  -18.0985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1249  -18.9010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417  -19.4382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3516  -19.1713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300  -16.4014    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    6.8655  -19.4847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1232  -21.5364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8720  -21.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4645  -22.0189    0.0000 O   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
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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 12 13  2  0
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 11 14  1  0
 17 18  2  0
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 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 19 23  1  0
 23 24  1  0
 25 26  1  0
 24 25  1  0
 26 27  1  0
 27 28  1  0
 28 24  1  0
 25 29  2  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 22 33  1  0
 26 16  1  0
 16 34  1  0
 34 15  1  0
 15 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38  1  1  0
  6 39  1  0
 39 40  2  0
 39 41  1  0
M  CHG  4  30   1  32  -1  39   1  41  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2286696

   (NZ)-N-[1-[(6-chloropyridin-3-yl)methyl]-3-[3-[3-[(2E)-3-[(6-chloropyridin-3-yl)methyl]-2-nitroiminoimidazolidin-1-yl]propoxy]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: 609.48

Molecular Weight (Monoisotopic): 608.1778

AlogP: 2.61

#Rotatable Bonds: 14

Polar Surface Area: 158.97

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 15

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 0.12

CX LogP: 1.49

CX LogD: 1.49

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.13

Np Likeness Score: -0.71

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