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

ID: ALA2288920

PubChem CID: 71518121

Max Phase: Preclinical

Molecular Formula: C17H21ClN4O3

Molecular Weight: 364.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOc1c([N+](=O)[O-])c2n(c1C)CCN2Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C17H21ClN4O3/c1-3-4-9-25-16-12(2)21-8-7-20(17(21)15(16)22(23)24)11-13-5-6-14(18)19-10-13/h5-6,10H,3-4,7-9,11H2,1-2H3

Standard InChI Key:  JXCDUQNDNWBZQC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   34.2627  -13.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0679  -13.8592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1965  -14.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4688  -15.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8905  -14.4583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6844  -13.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9526  -13.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0844  -14.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8120  -12.3462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1759  -11.8312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5759  -12.0552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5060  -14.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2291  -13.1523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5658  -13.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7680  -13.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4998  -14.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4814  -13.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1814  -13.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8989  -13.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9132  -14.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2132  -15.0427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.6306  -15.0162    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.8199  -13.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1579  -13.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4120  -13.4443    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
 23 24  1  0
 24 25  1  0
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288920

   6-Butoxy-1-[(6-chloropyridin-3-yl)methyl]-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: 364.83

Molecular Weight (Monoisotopic): 364.1302

AlogP: 3.95

#Rotatable Bonds: 7

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: 3.94

CX LogD: 3.94

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.32

Np Likeness Score: -1.40

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