Ethyl 2-methyl-3-nitroimidazo[1,2-a]pyrrolo[3,2-c]pyridine-8-carboxylate

ID: ALA1087599

PubChem CID: 135894287

Max Phase: Preclinical

Molecular Formula: C13H12N4O4

Molecular Weight: 288.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2c(ccn3c([N+](=O)[O-])c(C)nc23)[nH]1

Standard InChI:  InChI=1S/C13H12N4O4/c1-3-21-13(18)10-6-8-9(15-10)4-5-16-11(8)14-7(2)12(16)17(19)20/h4-6,15H,3H2,1-2H3

Standard InChI Key:  MFPIRANNNHSOSD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    8.5973  -17.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4238  -17.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8349  -17.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4238  -16.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5973  -16.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1861  -17.1811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6425  -17.3498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9751  -18.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7270  -18.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0460  -18.5029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2898  -18.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3786  -17.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4447  -18.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4447  -19.4041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1582  -18.1666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7642  -16.7964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9360  -15.9884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9677  -17.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5764  -18.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8717  -18.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5852  -18.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  1  0
  8  9  2  0
  7  9  1  0
  2  8  1  0
  3  7  1  0
 10 11  1  0
 11 12  2  0
  6 12  1  0
  1 10  2  0
 13 14  2  0
 13 15  1  0
  9 13  1  0
 16 17  2  0
 16 18  1  0
 12 16  1  0
 11 19  1  0
 20 21  1  0
 15 20  1  0
M  CHG  2  16   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1087599

   ---

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: 288.26

Molecular Weight (Monoisotopic): 288.0859

AlogP: 2.21

#Rotatable Bonds: 3

Polar Surface Area: 102.53

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.65

CX Basic pKa: 2.02

CX LogP: 1.30

CX LogD: 1.28

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.45

Np Likeness Score: -1.27

References

1. Chezal JM, Paeshuyse J, Gaumet V, Canitrot D, Maisonial A, Lartigue C, Gueiffier A, Moreau E, Teulade JC, Chavignon O, Neyts J..  (2010)  Synthesis and antiviral activity of an imidazo[1,2-a]pyrrolo[2,3-c]pyridine series against the bovine viral diarrhea virus.,  45  (5): [PMID:20149501] [10.1016/j.ejmech.2010.01.023]

Source

Source(1):

• Scientific Literature