Ethyl 1-hydroxy-4-methyl-2-(2-nitrophenyl)-1H-imidazole-5-carboxylate

ID: ALA5291280

Max Phase: Preclinical

Molecular Formula: C12H11N3O6

Molecular Weight: 293.24

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1c(O)nc(-c2ccccc2[N+](=O)[O-])n1O

Standard InChI:  InChI=1S/C12H11N3O6/c1-2-21-12(17)9-11(16)13-10(14(9)18)7-5-3-4-6-8(7)15(19)20/h3-6,16,18H,2H2,1H3

Standard InChI Key:  PASYMHQEKUTTAV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.8223   -0.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2346    0.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8227    0.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975    0.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5857    0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -0.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7605    0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3480    0.8325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4735    0.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5543   -0.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2055   -0.4864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2690   -0.5669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0570    1.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540    1.0170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    1.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8434    2.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7605    1.5471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5812   -1.3130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -2.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7561   -1.3131    0.0000 O   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
 19  6  1  0
 19 20  1  0
 19 21  2  0
M  CHG  2  19   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5291280

   ---

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: 293.24

Molecular Weight (Monoisotopic): 293.0648

AlogP: 1.58

#Rotatable Bonds: 4

Polar Surface Area: 127.72

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.89

CX Basic pKa: ┄

CX LogP: 2.37

CX LogD: 2.25

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.38

Np Likeness Score: -0.90

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