1-Butyl-2-methyl-3-octyl-4,9-dioxo-1H,4H,9H,-imidazo[4,5-g]quinoline-3-ium bromide

ID: ALA4876938

PubChem CID: 164625768

Max Phase: Preclinical

Molecular Formula: C23H32BrN3O2

Molecular Weight: 382.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCn1c2c([n+](CCCC)c1C)C(=O)c1cccnc1C2=O.[Br-]

Standard InChI:  InChI=1S/C23H32N3O2.BrH/c1-4-6-8-9-10-11-16-26-17(3)25(15-7-5-2)20-21(26)23(28)19-18(22(20)27)13-12-14-24-19;/h12-14H,4-11,15-16H2,1-3H3;1H/q+1;/p-1

Standard InChI Key:  YXAOYOLBXYSNKZ-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   40.1699  -21.1254    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   34.2188  -20.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2177  -21.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9324  -22.2273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.9306  -20.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6459  -20.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6448  -21.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3617  -22.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3640  -20.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0855  -20.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0822  -21.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8717  -22.0767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3630  -21.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8770  -20.7319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3607  -23.0567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3641  -19.7407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1880  -21.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1236  -22.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9298  -23.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1815  -23.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9879  -23.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1351  -19.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9427  -19.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2007  -18.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0084  -18.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2396  -24.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0459  -24.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2977  -25.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1040  -25.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  6  9  1  0
  7  8  1  0
  8 11  1  0
 10  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
  8 15  2  0
  9 16  2  0
 13 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 14 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
M  CHG  2   1  -1  14   1
M  END

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: 382.53

Molecular Weight (Monoisotopic): 382.2489

AlogP: 4.42

#Rotatable Bonds: 10

Polar Surface Area: 55.84

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.76

CX LogP: 0.55

CX LogD: 0.55

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.39

Np Likeness Score: -0.06

References

1. Fridianto KT, Li M, Hards K, Negatu DA, Cook GM, Dick T, Lam Y, Go ML..  (2021)  Functionalized Dioxonaphthoimidazoliums: A Redox Cycling Chemotype with Potent Bactericidal Activities against Mycobacterium tuberculosis.,  64  (21.0): [PMID:34706190] [10.1021/acs.jmedchem.1c01383]

Source

Source(1):

• Scientific Literature