6-Methyl-7-(4-methylbenzyl)-2-nitroimidazo[1,2-a]pyrazin-8(7H)-one

ID: ALA4579641

PubChem CID: 155565284

Max Phase: Preclinical

Molecular Formula: C15H14N4O3

Molecular Weight: 298.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(Cn2c(C)cn3cc([N+](=O)[O-])nc3c2=O)cc1

Standard InChI:  InChI=1S/C15H14N4O3/c1-10-3-5-12(6-4-10)8-18-11(2)7-17-9-13(19(21)22)16-14(17)15(18)20/h3-7,9H,8H2,1-2H3

Standard InChI Key:  LWQHHKPHEJOPJS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   11.9148  -16.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6242  -16.3975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6242  -15.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9148  -15.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2054  -16.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2009  -15.5762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4183  -15.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9374  -15.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4255  -16.6583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1113  -16.0017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7066  -16.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6988  -15.2921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9148  -17.6274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3336  -15.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3355  -16.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3328  -17.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6214  -18.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6184  -18.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3253  -19.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0367  -18.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0362  -18.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3237  -20.0761    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
  3 14  1  0
  2 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
M  CHG  2  10   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4579641

   ---

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: 298.30

Molecular Weight (Monoisotopic): 298.1066

AlogP: 2.07

#Rotatable Bonds: 3

Polar Surface Area: 82.44

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.92

CX LogD: 2.92

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.55

Np Likeness Score: -1.63

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]

Source

Source(1):

• Scientific Literature