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

ID: ALA2288917

PubChem CID: 71518118

Max Phase: Preclinical

Molecular Formula: C14H15ClN4O3

Molecular Weight: 322.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c([N+](=O)[O-])c2n(c1C)CCN2Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C14H15ClN4O3/c1-9-13(22-2)12(19(20)21)14-17(5-6-18(9)14)8-10-3-4-11(15)16-7-10/h3-4,7H,5-6,8H2,1-2H3

Standard InChI Key:  WEUGUUBLDNKQLQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    3.5355  -13.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3407  -13.7725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4693  -14.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416  -14.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1633  -14.3716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572  -13.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254  -13.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3572  -14.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848  -12.2596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4486  -11.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487  -11.9685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7788  -14.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5019  -13.0656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386  -13.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0375  -13.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7785  -14.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7540  -13.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4508  -13.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1712  -13.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917  -14.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4949  -14.9397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9122  -14.9024    0.0000 Cl  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
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288917

   1-[(6-Chloropyridin-3-yl)methyl]-6-methoxy-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: 322.75

Molecular Weight (Monoisotopic): 322.0833

AlogP: 2.78

#Rotatable Bonds: 4

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: 2.62

CX LogD: 2.62

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.49

Np Likeness Score: -1.48

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