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

ID: ALA4175661

PubChem CID: 134816495

Max Phase: Preclinical

Molecular Formula: C25H20FN5

Molecular Weight: 409.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2ccc(F)cc2)cc(C)c1Nc1ccnc(Nc2ccc(C#N)cc2)n1

Standard InChI:  InChI=1S/C25H20FN5/c1-16-13-20(19-5-7-21(26)8-6-19)14-17(2)24(16)30-23-11-12-28-25(31-23)29-22-9-3-18(15-27)4-10-22/h3-14H,1-2H3,(H2,28,29,30,31)

Standard InChI Key:  ICUMRVYQEMSBSV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    3.8369  -15.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8358  -16.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5438  -16.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2535  -16.3704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2506  -15.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5420  -15.1384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9609  -15.1324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9578  -14.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1291  -15.1388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289  -14.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8389  -13.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8391  -13.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1307  -12.6895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208  -13.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241  -13.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6616  -13.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6589  -13.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9491  -12.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2406  -13.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2468  -13.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5458  -14.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7179  -14.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9421  -11.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9380  -11.0531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1286  -11.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373  -11.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8363  -10.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1275  -10.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4181  -10.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4225  -11.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269   -9.4246    0.0000 F   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
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4175661

   ---

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: 409.47

Molecular Weight (Monoisotopic): 409.1703

AlogP: 6.26

#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: 6.88

CX LogD: 6.88

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: -1.54

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