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

ID: ALA4204987

PubChem CID: 145978057

Max Phase: Preclinical

Molecular Formula: C20H16N4O5

Molecular Weight: 392.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(OC)c1Oc1cnc([N+](=O)[O-])c(Nc2ccc(C#N)cc2)c1

Standard InChI:  InChI=1S/C20H16N4O5/c1-27-17-4-3-5-18(28-2)19(17)29-15-10-16(20(22-12-15)24(25)26)23-14-8-6-13(11-21)7-9-14/h3-10,12,23H,1-2H3

Standard InChI Key:  BJGWGFXHZBGPBM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   38.3951   -5.7024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1069   -6.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1025   -6.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8134   -7.3435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.5264   -6.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5239   -6.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8124   -5.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2344   -5.6944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6832   -6.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9749   -5.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2676   -6.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2669   -6.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9795   -7.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6880   -6.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2317   -4.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9382   -4.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9359   -3.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2263   -3.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5134   -3.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5193   -4.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2422   -7.3414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.9495   -6.9279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.2431   -8.1627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.2240   -2.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2202   -1.5960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9764   -4.8818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3981   -7.3320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.4027   -8.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2694   -4.4719    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
 27 28  1  0
 26 29  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4204987

   ---

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: 392.37

Molecular Weight (Monoisotopic): 392.1121

AlogP: 4.41

#Rotatable Bonds: 7

Polar Surface Area: 119.54

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.91

CX Basic pKa: ┄

CX LogP: 5.07

CX LogD: 5.07

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -1.13

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