5-(((6-Chloropyridin-3-yl)methyl)(ethyl)amino)-3-isopropoxy-1,2-dimethyl-4-nitro-2,3-dihydro-1H-pyrrol-2-ol

ID: ALA2288924

PubChem CID: 71518284

Max Phase: Preclinical

Molecular Formula: C17H25ClN4O4

Molecular Weight: 384.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(Cc1ccc(Cl)nc1)C1=C([N+](=O)[O-])C(OC(C)C)C(C)(O)N1C

Standard InChI:  InChI=1S/C17H25ClN4O4/c1-6-21(10-12-7-8-13(18)19-9-12)16-14(22(24)25)15(26-11(2)3)17(4,23)20(16)5/h7-9,11,15,23H,6,10H2,1-5H3

Standard InChI Key:  MXBKUBZVMVRHIU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   32.3096  -16.6812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0950  -16.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0950  -17.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3096  -18.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8294  -17.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9096  -17.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0590  -18.7891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2565  -18.9640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5741  -19.4253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2617  -16.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0590  -15.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7583  -18.2373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5097  -17.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0081  -17.3445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5954  -16.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7740  -16.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5954  -18.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3655  -17.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7740  -18.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3655  -18.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5441  -18.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1314  -18.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5441  -17.3445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3101  -18.0536    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.1736  -18.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5974  -17.0863    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  2  0
  1  5  1  0
  2  6  1  0
  7  8  2  0
  7  9  1  0
  4  7  1  0
  2 10  1  0
  1 11  1  0
 12 13  1  0
  3 12  1  0
 15 16  1  0
 14 15  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 22 24  1  0
 17 19  1  0
 14 17  1  0
  5 14  1  0
 13 25  1  0
 13 26  1  0
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288924

   5-[(6-chloropyridin-3-yl)methyl-ethylamino]-1,2-dimethyl-4-nitro-3-propan-2-yloxy-3H-pyrrol-2-ol

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: 384.86

Molecular Weight (Monoisotopic): 384.1564

AlogP: 2.45

#Rotatable Bonds: 7

Polar Surface Area: 91.97

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: 2.16

CX LogP: 2.48

CX LogD: 2.48

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: -0.72

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