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

ID: ALA2288929

PubChem CID: 71517944

Max Phase: Preclinical

Molecular Formula: C17H23ClN4O4

Molecular Weight: 382.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC1C([N+](=O)[O-])=C2N(Cc3ccc(Cl)nc3)CCN2C1(C)OCC

Standard InChI:  InChI=1S/C17H23ClN4O4/c1-4-25-15-14(22(23)24)16-20(11-12-6-7-13(18)19-10-12)8-9-21(16)17(15,3)26-5-2/h6-7,10,15H,4-5,8-9,11H2,1-3H3

Standard InChI Key:  SAGYHGVAVOEZDM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   15.4163   -4.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4151   -5.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1310   -6.1847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8486   -5.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8458   -4.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1292   -4.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6992   -6.1837    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.5597   -4.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3503   -4.7632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6178   -5.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4433   -5.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0088   -4.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6788   -4.7358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3352   -4.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0685   -3.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2472   -3.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7455   -2.8262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9260   -2.9271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0699   -2.0656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5391   -2.7849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7450   -4.9498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0478   -3.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3617   -2.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5707   -4.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7136   -3.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9831   -4.2371    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
 23 25  1  0
 24 26  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288929

   1-[(6-chloropyridin-3-yl)methyl]-5,6-diethoxy-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: 382.85

Molecular Weight (Monoisotopic): 382.1408

AlogP: 2.47

#Rotatable Bonds: 7

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: 1.85

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.41

Np Likeness Score: -0.60

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