N-(1-(2-(1-hydroxy-3-methyl-1-(3-(trifluoromethyl)phenyl)butyl)-1H-imidazol-4-yl)-2-oxo-1,2-dihydropyridin-4-yl)thiazole-4-carboxamide

ID: ALA3808401

PubChem CID: 127043428

Max Phase: Preclinical

Molecular Formula: C24H22F3N5O3S

Molecular Weight: 517.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CC(O)(c1cccc(C(F)(F)F)c1)c1nc(-n2ccc(NC(=O)c3cscn3)cc2=O)c[nH]1

Standard InChI:  InChI=1S/C24H22F3N5O3S/c1-14(2)10-23(35,15-4-3-5-16(8-15)24(25,26)27)22-28-11-19(31-22)32-7-6-17(9-20(32)33)30-21(34)18-12-36-13-29-18/h3-9,11-14,35H,10H2,1-2H3,(H,28,31)(H,30,34)

Standard InChI Key:  VEYOCGAKDPCFHN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
    3.9263   -5.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8082   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6149   -4.5391    0.0000 O   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 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
   -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
   -2.6003    1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -0.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5517    0.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5554    1.9869    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8054    3.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3382    2.9741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531   -1.9978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010   -3.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.9815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3006   -4.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9078   -6.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3992   -6.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2835   -5.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6762   -3.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1848   -3.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0068   -7.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3000   -8.6991    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.2000   -7.8569    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.4931   -8.8263    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5361   -7.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8310   -8.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7295   -7.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  2  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 12  1  0
  4 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 19  1  0
 22  2  1  0
  2 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 26 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
  1 34  1  0
 34 35  1  0
 34 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3808401

   ---

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: 517.53

Molecular Weight (Monoisotopic): 517.1395

AlogP: 4.57

#Rotatable Bonds: 7

Polar Surface Area: 112.90

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.93

CX Basic pKa: 0.13

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.33

Np Likeness Score: -1.36

References

1. Fader L, Brault M, Desjardins J, Dansereau N, Lamorte L, Tremblay S, Bilodeau F, Bordeleau J, Duplessis M, Gorys V, Gillard J, Gleason JL, James C, Joly MA, Kuhn C, Llinas-Brunet M, Luo L, Morency L, Morin S, Parisien M, Poirier M, Thibeault C, Trinh T, Sturino C, Srivastava S, Yoakim C, Franti M..  (2016)  Discovery of Potent, Orally Bioavailable Inhibitors of Human Cytomegalovirus.,  7  (5): [PMID:27190604] [10.1021/acsmedchemlett.6b00064]

Source

Source(1):

• Scientific Literature