4-((5-((4-cyanophenyl)amino)-6-nitropyridin-3-yl)oxy)-3,5-dimethylbenzonitrile

ID: ALA4207882

PubChem CID: 145977455

Max Phase: Preclinical

Molecular Formula: C21H15N5O3

Molecular Weight: 385.38

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H15N5O3/c1-13-7-16(11-23)8-14(2)20(13)29-18-9-19(21(24-12-18)26(27)28)25-17-5-3-15(10-22)4-6-17/h3-9,12,25H,1-2H3

Standard InChI Key:  FRFZYTVVWCDYSE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    5.0636   -5.6446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7754   -6.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7710   -6.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4819   -7.2857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1949   -6.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1924   -6.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4810   -5.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9029   -5.6367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3517   -6.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6434   -5.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9361   -6.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9354   -6.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6480   -7.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3565   -6.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9002   -4.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6067   -4.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6044   -3.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8948   -3.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1819   -3.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1878   -4.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9107   -7.2836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6180   -6.8701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9116   -8.1049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8925   -2.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8887   -1.5382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2274   -7.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5192   -7.6901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6449   -4.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0666   -7.2742    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
 26 27  3  0
 12 26  1  0
 10 28  1  0
 14 29  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4207882

   ---

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: 385.38

Molecular Weight (Monoisotopic): 385.1175

AlogP: 4.89

#Rotatable Bonds: 5

Polar Surface Area: 124.87

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.92

CX Basic pKa: ┄

CX LogP: 6.27

CX LogD: 6.27

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -1.21

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