4-((4-((3',5'-dichloro-3,5-dimethyl-(1,1'-biphenyl)-4-yl)amino)pyrimidin-2-yl)amino)benzonitrile

ID: ALA4176144

PubChem CID: 134816247

Max Phase: Preclinical

Molecular Formula: C25H19Cl2N5

Molecular Weight: 460.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2cc(Cl)cc(Cl)c2)cc(C)c1Nc1ccnc(Nc2ccc(C#N)cc2)n1

Standard InChI:  InChI=1S/C25H19Cl2N5/c1-15-9-18(19-11-20(26)13-21(27)12-19)10-16(2)24(15)31-23-7-8-29-25(32-23)30-22-5-3-17(14-28)4-6-22/h3-13H,1-2H3,(H2,29,30,31,32)

Standard InChI Key:  CLEYUGQORIJGAS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   22.4218   -9.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4207   -9.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1287  -10.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8384   -9.9278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8355   -9.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1269   -8.6958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5458   -8.6898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5428   -7.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7140   -8.6962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7138   -7.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4238   -7.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4240   -6.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7157   -6.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0057   -6.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0090   -7.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2465   -7.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2438   -6.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5340   -6.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8255   -6.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8318   -7.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1308   -7.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3028   -7.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5271   -5.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5229   -4.6105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7135   -5.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4222   -5.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4213   -4.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7124   -3.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0030   -4.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0074   -5.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1285   -3.7981    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.2941   -3.8026    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
  7  8  1  0
  1  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  8 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  8  1  0
 11 21  1  0
 15 22  1  0
 23 24  3  0
 18 23  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 13 25  1  0
 27 31  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4176144

   ---

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: 460.37

Molecular Weight (Monoisotopic): 459.1018

AlogP: 7.43

#Rotatable Bonds: 5

Polar Surface Area: 73.63

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.43

CX Basic pKa: 4.44

CX LogP: 7.94

CX LogD: 7.94

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: -1.44

References

1. Jin K, Yin H, De Clercq E, Pannecouque C, Meng G, Chen F..  (2018)  Discovery of biphenyl-substituted diarylpyrimidines as non-nucleoside reverse transcriptase inhibitors with high potency against wild-type and mutant HIV-1.,  145  [PMID:29353724] [10.1016/j.ejmech.2018.01.016]

Source

Source(1):

• Scientific Literature