2-Nitroimidazo[1,2-a]pyrazin-8(7H)-one

ID: ALA4580033

PubChem CID: 145998116

Max Phase: Preclinical

Molecular Formula: C6H4N4O3

Molecular Weight: 180.12

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1[nH]ccn2cc([N+](=O)[O-])nc12

Standard InChI:  InChI=1S/C6H4N4O3/c11-6-5-8-4(10(12)13)3-9(5)2-1-7-6/h1-3H,(H,7,11)

Standard InChI Key:  FQBHXGXXYYBSCO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 13 14  0  0  0  0  0  0  0  0999 V2000
   31.9236   -4.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6289   -3.6196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6289   -2.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9236   -2.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2184   -3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2139   -2.8024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4353   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9586   -3.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4426   -3.8763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9236   -4.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1366   -3.2238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7319   -3.9338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7241   -2.5184    0.0000 O   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
  1 10  2  0
 11 12  2  0
 11 13  1  0
  8 11  1  0
M  CHG  2  11   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4580033

   ---

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: 180.12

Molecular Weight (Monoisotopic): 180.0283

AlogP: -0.07

#Rotatable Bonds: 1

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: 11.17

CX Basic pKa: ┄

CX LogP: 0.25

CX LogD: 0.25

Aromatic Rings: 2

Heavy Atoms: 13

QED Weighted: 0.49

Np Likeness Score: -1.61

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