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

ID: ALA2288926

PubChem CID: 71518286

Max Phase: Preclinical

Molecular Formula: C15H19ClN4O3

Molecular Weight: 338.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(Cc1ccc(Cl)nc1)c1c([N+](=O)[O-])c(OC)c(C)n1C

Standard InChI:  InChI=1S/C15H19ClN4O3/c1-5-19(9-11-6-7-12(16)17-8-11)15-13(20(21)22)14(23-4)10(2)18(15)3/h6-8H,5,9H2,1-4H3

Standard InChI Key:  DFMZHMVQHUJJPM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   16.0029  -23.0640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5227  -22.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0029  -21.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7842  -21.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7842  -22.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7055  -22.4048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7523  -20.9643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9649  -20.7553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3307  -20.3860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4434  -23.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7523  -23.8412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4434  -21.5120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1907  -21.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2969  -21.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4798  -21.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2969  -23.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0712  -22.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4798  -23.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0712  -23.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2540  -23.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8454  -23.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2540  -22.4048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0282  -23.1098    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
  7  8  2  0
  7  9  1  0
  3  7  1  0
  5 10  1  0
  1 11  1  0
 12 13  1  0
  4 12  1  0
 14 15  1  0
  6 14  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 21 23  1  0
 16 18  1  0
  6 16  1  0
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288926

   N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-4-methoxy-1,5-dimethyl-3-nitropyrrol-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: 338.80

Molecular Weight (Monoisotopic): 338.1146

AlogP: 3.33

#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: 3.14

CX LogD: 3.14

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.46

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