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

ID: ALA2288928

PubChem CID: 71517943

Max Phase: Preclinical

Molecular Formula: C15H19ClN4O4

Molecular Weight: 354.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1C([N+](=O)[O-])=C2N(Cc3ccc(Cl)nc3)CCN2C1(C)OC

Standard InChI:  InChI=1S/C15H19ClN4O4/c1-15(24-3)13(23-2)12(20(21)22)14-18(6-7-19(14)15)9-10-4-5-11(16)17-8-10/h4-5,8,13H,6-7,9H2,1-3H3

Standard InChI Key:  XAYBFOISZSSFGO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    8.1502   -4.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1490   -5.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8607   -6.0469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5782   -5.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5753   -4.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8589   -4.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4332   -6.0460    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.2892   -4.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0797   -4.6256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3471   -5.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1725   -5.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7381   -4.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4121   -4.5982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0643   -4.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7976   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9764   -3.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4789   -2.6889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6595   -2.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7991   -1.9284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2724   -2.6476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4740   -4.8122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7768   -3.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0948   -2.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2996   -4.8141    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
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288928

   1-[(6-chloropyridin-3-yl)methyl]-5,6-dimethoxy-5-methyl-7-nitro-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: 354.79

Molecular Weight (Monoisotopic): 354.1095

AlogP: 1.69

#Rotatable Bonds: 5

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: 1.70

CX LogP: 1.82

CX LogD: 1.82

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.45

Np Likeness Score: -0.57

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