4-((6-((4-Chlorophenyl)amino)-2-(p-tolylamino)pyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile

ID: ALA3786888

PubChem CID: 127032824

Max Phase: Preclinical

Molecular Formula: C26H22ClN5O

Molecular Weight: 455.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(Nc2nc(Nc3ccc(Cl)cc3)cc(Oc3c(C)cc(C#N)cc3C)n2)cc1

Standard InChI:  InChI=1S/C26H22ClN5O/c1-16-4-8-22(9-5-16)30-26-31-23(29-21-10-6-20(27)7-11-21)14-24(32-26)33-25-17(2)12-19(15-28)13-18(25)3/h4-14H,1-3H3,(H2,29,30,31,32)

Standard InChI Key:  MBOYWUVYAFHSEQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    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
    2.5754   -8.7048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092    5.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -2.5805   -7.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9486    5.8368    0.0000 Cl  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
 10 11  1  0
 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
 29 32  1  0
 23 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3786888

   ---

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: 455.95

Molecular Weight (Monoisotopic): 455.1513

AlogP: 7.21

#Rotatable Bonds: 6

Polar Surface Area: 82.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.45

CX Basic pKa: 4.29

CX LogP: 8.30

CX LogD: 8.30

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.32

Np Likeness Score: -1.37

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