1-((6-Chloropyridin-3-yl)methyl)-5-methyl-7-nitro-5,6-dipropoxy-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazole

ID: ALA2288930

PubChem CID: 71517945

Max Phase: Preclinical

Molecular Formula: C19H27ClN4O4

Molecular Weight: 410.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOC1C([N+](=O)[O-])=C2N(Cc3ccc(Cl)nc3)CCN2C1(C)OCCC

Standard InChI:  InChI=1S/C19H27ClN4O4/c1-4-10-27-17-16(24(25)26)18-22(13-14-6-7-15(20)21-12-14)8-9-23(18)19(17,3)28-11-5-2/h6-7,12,17H,4-5,8-11,13H2,1-3H3

Standard InChI Key:  PZRJOGGFDLKUNJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   23.1421   -5.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1409   -5.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8564   -6.3048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5693   -5.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5664   -5.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8546   -4.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4256   -6.3038    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.2800   -4.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0700   -4.8842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3415   -5.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1664   -5.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7281   -4.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4016   -4.8568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0577   -4.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7870   -3.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9663   -3.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4690   -2.9486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6501   -3.0494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7891   -2.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2614   -2.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4630   -5.0707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7698   -3.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0834   -2.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2880   -5.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4310   -3.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7044   -4.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2530   -3.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5295   -4.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12  9  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
 17 18  2  0
 17 19  1  0
 16 17  1  0
 15 20  1  0
 14 21  1  0
 14 22  1  0
 20 23  1  0
 21 24  1  0
 23 25  1  0
 24 26  1  0
 25 27  1  0
 26 28  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288930

   1-[(6-chloropyridin-3-yl)methyl]-5-methyl-7-nitro-5,6-dipropoxy-3,6-dihydro-2H-pyrrolo[1,2-a]imidazole

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: 410.90

Molecular Weight (Monoisotopic): 410.1721

AlogP: 3.25

#Rotatable Bonds: 9

Polar Surface Area: 80.97

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.85

CX LogP: 3.58

CX LogD: 3.58

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.35

Np Likeness Score: -0.70

References

1. Ye Z, Shi L, Shao X, Xu X, Xu Z, Li Z..  (2013)  Pyrrole- and dihydropyrrole-fused neonicotinoids: design, synthesis, and insecticidal evaluation.,  61  (2): [PMID:23256728] [10.1021/jf3044132]

Source

Source(1):

• Scientific Literature