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

ID: ALA4217843

PubChem CID: 145974983

Max Phase: Preclinical

Molecular Formula: C20H15ClN4O3

Molecular Weight: 394.82

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H15ClN4O3/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:  KPYPVTVWDXFNLT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    4.3496  -13.5359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0614  -13.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0570  -14.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7679  -15.1770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4808  -14.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4784  -13.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7669  -13.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1889  -13.5279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6377  -13.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9294  -13.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2220  -13.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2214  -14.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9340  -15.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425  -14.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1862  -12.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8927  -12.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8903  -11.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1808  -11.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4679  -11.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4738  -12.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1967  -15.1749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9040  -14.7614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1976  -15.9962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1785  -10.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1747   -9.4295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9309  -12.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3525  -15.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133  -15.1702    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
  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:

   

   ALA4217843

   ---

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: 394.82

Molecular Weight (Monoisotopic): 394.0833

AlogP: 5.67

#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: 7.02

CX LogD: 7.02

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -1.47

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