(E)-4-((4-chloro-6-(4-(2-cyanovinyl)-2,6-dimethylphenoxy)pyrimidin-2-yl)amino)benzonitrile

ID: ALA4228362

PubChem CID: 134816989

Max Phase: Preclinical

Molecular Formula: C22H16ClN5O

Molecular Weight: 401.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(/C=C/C#N)cc(C)c1Oc1cc(Cl)nc(Nc2ccc(C#N)cc2)n1

Standard InChI:  InChI=1S/C22H16ClN5O/c1-14-10-17(4-3-9-24)11-15(2)21(14)29-20-12-19(23)27-22(28-20)26-18-7-5-16(13-25)6-8-18/h3-8,10-12H,1-2H3,(H,26,27,28)/b4-3+

Standard InChI Key:  YDFFSHCXESSOAN-ONEGZZNKSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   14.5549  -26.1442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8417  -25.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1244  -25.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4176  -25.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7016  -25.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7016  -24.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4150  -24.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1244  -24.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9886  -24.0833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9886  -23.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2685  -22.8537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2685  -22.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9860  -21.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6954  -22.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6954  -22.8485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5554  -21.6128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8422  -22.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8478  -22.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5610  -23.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1271  -23.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4135  -22.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7004  -23.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873  -22.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2702  -23.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5570  -23.6703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4168  -22.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1288  -21.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1288  -20.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4099  -21.6105    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  3  0
  3  2  1  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  7  6  2  0
  8  7  1  0
  3  8  2  0
  9  6  1  0
 10  9  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 10 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 20 18  2  0
 21 20  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  3  0
 26 21  2  0
 27 26  1  0
 27 28  1  0
 17 27  2  0
 14 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4228362

   ---

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: 401.86

Molecular Weight (Monoisotopic): 401.1043

AlogP: 5.69

#Rotatable Bonds: 5

Polar Surface Area: 94.62

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.59

CX Basic pKa: 0.64

CX LogP: 6.36

CX LogD: 6.36

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: -1.08

References

1. Lu X, Yang J, Kang D, Gao P, Daelemans D, De Clercq E, Pannecouque C, Zhan P, Liu X..  (2018)  The discovery of novel diarylpyri(mi)dine derivatives with high level activity against a wide variety of HIV-1 strains as well as against HIV-2.,  26  (8): [PMID:29559197] [10.1016/j.bmc.2018.03.003]

Source

Source(1):

• Scientific Literature