4-((5-(4-bromo-2,6-dimethylphenoxy)-2-nitropyridin-3-yl)amino)benzonitrile

ID: ALA4206980

PubChem CID: 145976417

Max Phase: Preclinical

Molecular Formula: C20H15BrN4O3

Molecular Weight: 439.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(Br)cc(C)c1Oc1cnc([N+](=O)[O-])c(Nc2ccc(C#N)cc2)c1

Standard InChI:  InChI=1S/C20H15BrN4O3/c1-12-7-15(21)8-13(2)19(12)28-17-9-18(20(23-11-17)25(26)27)24-16-5-3-14(10-22)4-6-16/h3-9,11,24H,1-2H3

Standard InChI Key:  QCBSXIVWWBGSHY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   13.0003  -13.5813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7120  -13.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7077  -14.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4186  -15.2224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1315  -14.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1291  -13.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4176  -13.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8396  -13.5733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2884  -13.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5800  -13.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8727  -13.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8721  -14.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5847  -15.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2932  -14.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8369  -12.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5433  -12.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5410  -11.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8314  -11.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1186  -11.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1244  -12.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8474  -15.2203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5547  -14.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8483  -16.0416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8291  -10.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8254   -9.4749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5816  -12.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0032  -15.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1639  -15.2156    0.0000 Br  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
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  1  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 21 22  2  0
 21 23  1  0
  5 21  1  0
 24 25  3  0
 18 24  1  0
 10 26  1  0
 14 27  1  0
 12 28  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4206980

   ---

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: 439.27

Molecular Weight (Monoisotopic): 438.0328

AlogP: 5.78

#Rotatable Bonds: 5

Polar Surface Area: 101.08

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.92

CX Basic pKa: ┄

CX LogP: 7.18

CX LogD: 7.18

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.40

Np Likeness Score: -1.36

References

1. Liu Z, Tian Y, Liu J, Huang B, Kang D, De Clercq E, Daelemans D, Pannecouque C, Zhan P, Liu X..  (2017)  Design, synthesis and anti-HIV evaluation of novel diarylpyridine derivatives as potent HIV-1 NNRTIs.,  140  [PMID:28987601] [10.1016/j.ejmech.2017.07.012]

Source

Source(1):

• Scientific Literature