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

ID: ALA3808805

PubChem CID: 74223858

Max Phase: Preclinical

Molecular Formula: C21H16F3N5O3S

Molecular Weight: 475.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H16F3N5O3S/c1-20(32,12-3-2-4-13(7-12)21(22,23)24)19-25-9-16(28-19)29-6-5-14(8-17(29)30)27-18(31)15-10-33-11-26-15/h2-11,32H,1H3,(H,25,28)(H,27,31)

Standard InChI Key:  GRXACSZEXPOWKP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.1010   -5.6348    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
    3.6150   -4.5378    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
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   -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
    6.3005   -4.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9075   -6.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3990   -6.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2833   -5.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6763   -3.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1848   -3.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0064   -7.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2995   -8.6994    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.1996   -7.8574    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.4925   -8.8268    0.0000 F   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
M  END

Alternative Forms

1. Parent:

   

   ALA3808805

   N-[1-[2-[1-hydroxy-1-[3-(trifluoromethyl)phenyl]ethyl]-1H-imidazol-5-yl]-2-oxopyridin-4-yl]-1,3-thiazole-4-carboxamide

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: 475.45

Molecular Weight (Monoisotopic): 475.0926

AlogP: 3.54

#Rotatable Bonds: 5

Polar Surface Area: 112.90

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.95

CX Basic pKa: 0.13

CX LogP: 2.47

CX LogD: 2.47

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.41

Np Likeness Score: -1.50

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