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

ID: ALA2288918

PubChem CID: 71518119

Max Phase: Preclinical

Molecular Formula: C15H17ClN4O3

Molecular Weight: 336.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1c([N+](=O)[O-])c2n(c1C)CCN2Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C15H17ClN4O3/c1-3-23-14-10(2)19-7-6-18(15(19)13(14)20(21)22)9-11-4-5-12(16)17-8-11/h4-5,8H,3,6-7,9H2,1-2H3

Standard InChI Key:  ZGPKXEVBQDKKGK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   12.8424  -13.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6485  -13.8129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7762  -14.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0485  -14.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4702  -14.4129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2641  -13.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5323  -13.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6641  -14.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3917  -12.3008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7555  -11.7858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1556  -12.0098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0857  -14.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8088  -13.1069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1455  -13.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3617  -13.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0514  -14.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0610  -13.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7752  -13.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4786  -13.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4649  -14.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7507  -15.0705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1683  -15.0928    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.3996  -13.2534    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
  1  5  1  0
  6  7  1  0
  7  8  2  0
  5  8  1  0
  1  6  2  0
  9 10  2  0
  9 11  1  0
  6  9  1  0
  8 12  1  0
 13 14  1  0
  7 13  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  0
 20 22  1  0
 15 17  1  0
  2 15  1  0
 14 23  1  0
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288918

   1-[(6-Chloropyridin-3-yl)methyl]-6-ethoxy-5-methyl-7-nitro-2,3-dihydropyrrolo[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: 336.78

Molecular Weight (Monoisotopic): 336.0989

AlogP: 3.17

#Rotatable Bonds: 5

Polar Surface Area: 73.43

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.82

CX LogP: 2.97

CX LogD: 2.97

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.48

Np Likeness Score: -1.62

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