N-((6-Chloropyridin-3-yl)methyl)-N-ethyl-1,5-dimethyl-3-nitro-4-propoxy-1H-pyrrol-2-amine

ID: ALA2288658

PubChem CID: 71518457

Max Phase: Preclinical

Molecular Formula: C17H23ClN4O3

Molecular Weight: 366.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOc1c([N+](=O)[O-])c(N(CC)Cc2ccc(Cl)nc2)n(C)c1C

Standard InChI:  InChI=1S/C17H23ClN4O3/c1-5-9-25-16-12(3)20(4)17(15(16)22(23)24)21(6-2)11-13-7-8-14(18)19-10-13/h7-8,10H,5-6,9,11H2,1-4H3

Standard InChI Key:  VASLLEFBDWAETA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   33.3563  -22.9887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8761  -22.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3563  -21.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1335  -21.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1335  -22.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0589  -22.3254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7968  -21.4367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5441  -21.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2032  -21.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9505  -21.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1057  -20.8890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6841  -20.3107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3142  -20.6759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7968  -23.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1057  -23.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6503  -21.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8332  -21.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6503  -23.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4246  -22.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8332  -23.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4246  -23.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6074  -23.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1988  -23.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6074  -22.3254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3816  -23.0345    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  2  6  1  0
  8  9  1  0
  9 10  1  0
  7  8  1  0
  4  7  1  0
 11 12  2  0
 11 13  1  0
  3 11  1  0
  5 14  1  0
  1 15  1  0
 16 17  1  0
  6 16  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 23 25  1  0
 18 20  1  0
  6 18  1  0
M  CHG  2  11   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288658

   N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-1,5-dimethyl-3-nitro-4-propoxypyrrol-2-amine

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: 366.85

Molecular Weight (Monoisotopic): 366.1459

AlogP: 4.11

#Rotatable Bonds: 8

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: 4.02

CX LogD: 4.02

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.40

Np Likeness Score: -1.43

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