N-Cyclopropyl-1-hydroxy-4-methyl-2-(4-nitrophenyl)-1H-imidazole-5-carboxamide

ID: ALA5285582

Max Phase: Preclinical

Molecular Formula: C13H12N4O5

Molecular Weight: 304.26

Names and Identifiers

Canonical SMILES:  O=C(NC1CC1)c1c(O)nc(-c2ccc([N+](=O)[O-])cc2)n1O

Standard InChI:  InChI=1S/C13H12N4O5/c18-12(14-8-3-4-8)10-13(19)15-11(16(10)20)7-1-5-9(6-2-7)17(21)22/h1-2,5-6,8,19-20H,3-4H2,(H,14,18)

Standard InChI Key:  FFHCQVWMGVHOHP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    0.2700   -0.0669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1423    0.6475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1423   -0.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674   -0.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3790   -0.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2040   -0.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158   -0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036   -1.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753   -1.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.3855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722   -1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0914   -0.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6747    0.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    0.1175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0549    0.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4612    1.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8867   -1.4660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4408   -0.7831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8533   -0.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8533   -1.4975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8533    0.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694    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
 18  7  1  0
 18 19  1  0
 18 20  2  0
 21 15  1  0
 21 22  1  0
 15 22  1  0
M  CHG  2  18   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5285582

   ---

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: 304.26

Molecular Weight (Monoisotopic): 304.0808

AlogP: 1.29

#Rotatable Bonds: 4

Polar Surface Area: 130.52

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.31

CX Basic pKa: ┄

CX LogP: 1.55

CX LogD: 1.21

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.44

Np Likeness Score: -1.29

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