N-Cyclopropyl-1-hydroxy-4-methyl-2-[4-(trifluoromethyl)phenyl]-1H-imidazole-5-carboxamide

ID: ALA5283017

Max Phase: Preclinical

Molecular Formula: C14H12F3N3O3

Molecular Weight: 327.26

Names and Identifiers

Canonical SMILES:  O=C(NC1CC1)c1c(O)nc(-c2ccc(C(F)(F)F)cc2)n1O

Standard InChI:  InChI=1S/C14H12F3N3O3/c15-14(16,17)8-3-1-7(2-4-8)11-19-13(22)10(20(11)23)12(21)18-9-5-6-9/h1-4,9,22-23H,5-6H2,(H,18,21)

Standard InChI Key:  GYUKMCDOJHZTNR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    0.4763   -0.0668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    0.6475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638   -0.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611   -0.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728   -0.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9978   -0.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096   -0.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9974   -1.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691   -1.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6187   -1.3855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785   -1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2976   -0.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8810    0.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6778    0.1176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2612    0.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6674    1.1278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.4659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2346   -0.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6471   -1.4975    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6471   -0.0685    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0595   -0.7830    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.0595    0.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4756    1.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  1  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  4  2  0
  3 10  2  0
 10 11  1  0
 12 11  2  0
  1 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 11 17  1  0
  7 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 22 15  1  0
 22 23  1  0
 15 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283017

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 327.26

Molecular Weight (Monoisotopic): 327.0831

AlogP: 2.40

#Rotatable Bonds: 3

Polar Surface Area: 87.38

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.34

CX Basic pKa: ┄

CX LogP: 2.49

CX LogD: 2.16

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.76

Np Likeness Score: -1.20

References

1. Nikitina PA, Basanova EI, Nikolaenkova EB, Os'kina IA, Serova OA, Bormotov NI, Shishkina LN, Perevalov VP, Tikhonov AY..  (2023)  Synthesis of esters and amides of 2-aryl-1-hydroxy-4-methyl-1H-imidazole-5-carboxylic acids and study of their antiviral activity against orthopoxviruses.,  79  [PMID:36414175] [10.1016/j.bmcl.2022.129080]

Source

Source(1):

• Scientific Literature