2-chloro-5-{[(2E)-3-(4-{[(2E)-3-[(6-chloropyridin-3-yl)methyl]-2-(nitroimino)imidazolidin-1-yl]methyl}phenyl)-2-(nitroimino)imidazolidin-1-yl]methyl}pyridine

ID: ALA2286694

PubChem CID: 76330999

Max Phase: Preclinical

Molecular Formula: C25H24Cl2N10O4

Molecular Weight: 599.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])/N=C1\N(Cc2ccc(N3CCN(Cc4ccc(Cl)nc4)/C3=N\[N+](=O)[O-])cc2)CCN1Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C25H24Cl2N10O4/c26-22-7-3-19(13-28-22)16-33-10-9-32(24(33)30-36(38)39)15-18-1-5-21(6-2-18)35-12-11-34(25(35)31-37(40)41)17-20-4-8-23(27)29-14-20/h1-8,13-14H,9-12,15-17H2/b30-24+,31-25+

Standard InChI Key:  YTPCVZHOTWKRFR-AMLXCYGQSA-N

Molfile:  

     RDKit          2D

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   11.5357  -31.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0754  -24.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2569  -24.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8536  -25.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3000  -25.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7926  -25.7044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2278  -26.9544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2481  -28.0929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0365  -25.0562    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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  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
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  6 15  1  0
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 20 21  2  0
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 24 25  2  0
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 22 26  1  0
 26 27  1  0
 28 29  1  0
 27 28  1  0
 29 30  1  0
 30 31  1  0
 31 27  1  0
 28 32  2  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 25 36  1  0
 29 19  1  0
 19 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 18  1  0
 18 41  2  0
 41 37  1  0
 40  1  1  0
M  CHG  4  15   1  17  -1  33   1  35  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2286694

   (NE)-N-[1-[(6-chloropyridin-3-yl)methyl]-3-[4-[[(2E)-3-[(6-chloropyridin-3-yl)methyl]-2-nitroiminoimidazolidin-1-yl]methyl]phenyl]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: 599.44

Molecular Weight (Monoisotopic): 598.1359

AlogP: 3.52

#Rotatable Bonds: 9

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: 3.16

CX LogD: 3.16

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.20

Np Likeness Score: -0.80

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