5,6-Dimethyl-2-nitro-8-((2-(trifluoromethoxy)benzyl)oxy)imidazo[1,2-a]pyrazine

ID: ALA4527225

PubChem CID: 155544329

Max Phase: Preclinical

Molecular Formula: C16H13F3N4O4

Molecular Weight: 382.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc(OCc2ccccc2OC(F)(F)F)c2nc([N+](=O)[O-])cn2c1C

Standard InChI:  InChI=1S/C16H13F3N4O4/c1-9-10(2)22-7-13(23(24)25)21-14(22)15(20-9)26-8-11-5-3-4-6-12(11)27-16(17,18)19/h3-7H,8H2,1-2H3

Standard InChI Key:  YXZQKKUMXHZDHA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   42.8525   -3.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5619   -3.0129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.5619   -2.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8525   -1.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1431   -3.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1386   -2.1916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.3560   -1.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8792   -2.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3633   -3.2696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.0531   -2.6130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6443   -3.3271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.6365   -1.9075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.8525   -4.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.2713   -1.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5644   -4.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2762   -4.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9879   -4.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6993   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6997   -3.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9829   -3.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2745   -3.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8536   -0.9534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9867   -5.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.2743   -5.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2731   -6.7039    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   43.5631   -5.4729    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   43.5588   -6.2899    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  2  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  1  0
  3 14  1  0
 13 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
  4 22  1  0
 17 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
M  CHG  2  10   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4527225

   ---

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: 382.30

Molecular Weight (Monoisotopic): 382.0889

AlogP: 3.73

#Rotatable Bonds: 5

Polar Surface Area: 91.79

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.00

CX LogD: 4.00

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: -1.39

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