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

ID: ALA4208398

PubChem CID: 145977972

Max Phase: Preclinical

Molecular Formula: C20H16N4O3

Molecular Weight: 360.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C)c1Oc1cnc([N+](=O)[O-])c(Nc2ccc(C#N)cc2)c1

Standard InChI:  InChI=1S/C20H16N4O3/c1-13-4-3-5-14(2)19(13)27-17-10-18(20(22-12-17)24(25)26)23-16-8-6-15(11-21)7-9-16/h3-10,12,23H,1-2H3

Standard InChI Key:  LAXOFTDHOFUHKL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   29.8394   -5.2690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5511   -5.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5468   -6.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2577   -6.9101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9706   -6.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9682   -5.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2567   -5.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6787   -5.2611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1275   -5.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4191   -5.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7118   -5.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7112   -6.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4238   -6.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1323   -6.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6760   -4.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3824   -4.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3801   -3.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6705   -2.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9577   -3.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9635   -4.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6865   -6.9080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3938   -6.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6874   -7.7294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6682   -1.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6645   -1.1627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4207   -4.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8423   -6.8986    0.0000 C   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
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4208398

   ---

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: 360.37

Molecular Weight (Monoisotopic): 360.1222

AlogP: 5.01

#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: 6.41

CX LogD: 6.41

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.40

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