4-((2-((3-Cyanophenyl)amino)-6-((4-cyanophenyl)amino)pyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile

ID: ALA3785606

PubChem CID: 127032521

Max Phase: Preclinical

Molecular Formula: C27H19N7O

Molecular Weight: 457.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C#N)cc(C)c1Oc1cc(Nc2ccc(C#N)cc2)nc(Nc2cccc(C#N)c2)n1

Standard InChI:  InChI=1S/C27H19N7O/c1-17-10-21(16-30)11-18(2)26(17)35-25-13-24(31-22-8-6-19(14-28)7-9-22)33-27(34-25)32-23-5-3-4-20(12-23)15-29/h3-13H,1-2H3,(H2,31,32,33,34)

Standard InChI Key:  LOGPVZJAFOVNKK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8915   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2883   -5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9329   -3.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563   -3.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5795   -7.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6108    5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073    5.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9021    3.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6005    2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8915   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883   -5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935   -3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2096    5.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2509    6.5827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1835   -6.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2206   -6.6170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  1  8  1  0
  8  9  1  0
  9 10  2  0
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 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 10 15  1  0
 14 16  1  0
 12 17  1  0
 17 18  3  0
  3 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  7 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 23 32  1  0
 32 33  3  0
 28 34  1  0
 34 35  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA3785606

   ---

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: 457.50

Molecular Weight (Monoisotopic): 457.1651

AlogP: 5.99

#Rotatable Bonds: 6

Polar Surface Area: 130.44

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.01

CX Basic pKa: 3.98

CX LogP: 6.89

CX LogD: 6.89

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.36

Np Likeness Score: -1.35

References

1. Meng Q, Chen X, Kang D, Huang B, Li W, Zhan P, Daelemans D, De Clercq E, Pannecouque C, Liu X..  (2016)  Design, synthesis and evaluation of novel HIV-1 NNRTIs with dual structural conformations targeting the entrance channel of the NNRTI binding pocket.,  115  [PMID:26994843] [10.1016/j.ejmech.2016.02.068]

Source

Source(1):

• Scientific Literature