2-Nitro-6-phenylimidazo[1,2-a]pyrazin-8(7H)-one

ID: ALA4539535

PubChem CID: 145998118

Max Phase: Preclinical

Molecular Formula: C12H8N4O3

Molecular Weight: 256.22

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(-c2ccccc2)cn2cc([N+](=O)[O-])nc12

Standard InChI:  InChI=1S/C12H8N4O3/c17-12-11-14-10(16(18)19)7-15(11)6-9(13-12)8-4-2-1-3-5-8/h1-7H,(H,13,17)

Standard InChI Key:  VJNQLDGSWUPVIP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   20.9328   -4.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6381   -4.4161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6381   -3.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9328   -3.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2275   -4.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2230   -3.5990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4445   -3.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9678   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4518   -4.6729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1458   -4.0203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7411   -4.7303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7333   -3.3149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9328   -5.6378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3434   -3.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0502   -3.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7586   -3.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7614   -2.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0499   -1.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3444   -2.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  2  0
 10 11  2  0
 10 12  1  0
  8 10  1  0
  1 13  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  3 14  1  0
M  CHG  2  10   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4539535

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 256.22

Molecular Weight (Monoisotopic): 256.0596

AlogP: 1.60

#Rotatable Bonds: 2

Polar Surface Area: 93.30

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.37

CX Basic pKa: ┄

CX LogP: 1.55

CX LogD: 1.55

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.56

Np Likeness Score: -1.23

References

1. Jarrad AM, Ang CW, Debnath A, Hahn HJ, Woods K, Tan L, Sykes ML, Jones AJ, Pelingon R, Butler MS, Avery VM, West NP, Karoli T, Blaskovich MAT, Cooper MA..  (2018)  Design, Synthesis, and Biological Evaluation of 2-Nitroimidazopyrazin-one/-es with Antitubercular and Antiparasitic Activity.,  61  (24): [PMID:30468386] [10.1021/acs.jmedchem.8b01578]

2. Ang CW, Lee BM, Jackson CJ, Wang Y, Franzblau SG, Francisco AF, Kelly JM, Bernhardt PV, Tan L, West NP, Sykes ML, Hinton AO, Bolisetti R, Avery VM, Cooper MA, Blaskovich MAT..  (2022)  Nitroimidazopyrazinones with Oral Activity against Tuberculosis and Chagas Disease in Mouse Models of Infection.,  65  (19.0): [PMID:36111399] [10.1021/acs.jmedchem.2c00972]

Source

Source(1):

• Scientific Literature