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

ID: ALA2288919

PubChem CID: 71518120

Max Phase: Preclinical

Molecular Formula: C16H19ClN4O3

Molecular Weight: 350.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOc1c([N+](=O)[O-])c2n(c1C)CCN2Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C16H19ClN4O3/c1-3-8-24-15-11(2)20-7-6-19(16(20)14(15)21(22)23)10-12-4-5-13(17)18-9-12/h4-5,9H,3,6-8,10H2,1-2H3

Standard InChI Key:  SZHUCQGVJJDTKF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   23.3380  -13.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1471  -13.9955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2758  -14.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5441  -15.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9657  -14.5986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7555  -13.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0237  -13.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1555  -14.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8873  -12.4783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2470  -11.9591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6552  -12.1832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5730  -15.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2961  -13.2885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6287  -13.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8657  -13.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5587  -14.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5689  -14.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2875  -13.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9947  -14.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9805  -14.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2619  -15.2619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6835  -15.2852    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.8786  -13.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2125  -13.9142    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
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288919

   1-[(6-Chloropyridin-3-yl)methyl]-5-methyl-7-nitro-6-propoxy-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: 350.81

Molecular Weight (Monoisotopic): 350.1146

AlogP: 3.56

#Rotatable Bonds: 6

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: 3.49

CX LogD: 3.49

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.45

Np Likeness Score: -1.52

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