1,3-Dihexyl-2-methyl-4,9-dioxo-4,9-dihydro-3H-imidazo[4,5-g]quinolin-1-ium bromide

ID: ALA4860219

PubChem CID: 164613732

Max Phase: Preclinical

Molecular Formula: C23H32BrN3O2

Molecular Weight: 382.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCn1c2c([n+](CCCCCC)c1C)C(=O)c1cccnc1C2=O.[Br-]

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

Standard InChI Key:  LOZDOUWDAQIFHY-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   32.3503  -20.0849    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   25.9398  -20.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9387  -21.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6535  -21.8857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6517  -20.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3670  -20.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3659  -21.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0828  -21.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0851  -20.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8066  -20.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8033  -21.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5927  -21.7351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0841  -21.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5981  -20.3903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0818  -22.7152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0852  -19.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9091  -21.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8445  -22.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6508  -22.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9026  -23.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7089  -23.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8561  -19.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6638  -19.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9218  -18.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7294  -18.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9875  -17.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7951  -17.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9607  -24.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7669  -24.6162    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
 25 26  1  0
 26 27  1  0
 21 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: -0.08

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