Ethyl 1-hydroxy-4-methyl-2-[4-(trifluoromethyl)phenyl]-1H-imidazole-5-carboxylate

ID: ALA5280323

Max Phase: Preclinical

Molecular Formula: C13H11F3N2O4

Molecular Weight: 316.24

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H11F3N2O4/c1-2-22-12(20)9-11(19)17-10(18(9)21)7-3-5-8(6-4-7)13(14,15)16/h3-6,19,21H,2H2,1H3

Standard InChI Key:  QAVTUHMBMRUHKF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -1.9971   -1.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094   -0.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975    0.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1723    0.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7605   -0.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1686   -1.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0646   -0.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772    0.1179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2986   -0.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3795   -0.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6197   -1.2010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0942   -1.2815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8822    0.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6793    0.3024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627    0.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0598    0.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6686    1.3130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645    0.8326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2346   -0.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6472   -1.3130    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6472    0.1161    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0598   -0.5984    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  7  5  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 11 10  1  0
  7 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  2  0
  8 18  1  0
  2 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280323

   ---

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: 316.24

Molecular Weight (Monoisotopic): 316.0671

AlogP: 2.69

#Rotatable Bonds: 3

Polar Surface Area: 84.58

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.22

CX Basic pKa: ┄

CX LogP: 3.31

CX LogD: 3.25

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.67

Np Likeness Score: -1.00

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