1,3-Dihexyl-2-methyl-4,9-dioxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-ium bromide

ID: ALA4860887

PubChem CID: 164614762

Max Phase: Preclinical

Molecular Formula: C24H33BrN2O2

Molecular Weight: 381.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCn1c2c([n+](CCCCCC)c1C)C(=O)c1ccccc1C2=O.[Br-]

Standard InChI:  InChI=1S/C24H33N2O2.BrH/c1-4-6-8-12-16-25-18(3)26(17-13-9-7-5-2)22-21(25)23(27)19-14-10-11-15-20(19)24(22)28;/h10-11,14-15H,4-9,12-13,16-17H2,1-3H3;1H/q+1;/p-1

Standard InChI Key:  YTSPRFVDSQXJGY-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   41.9671  -25.1614    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   35.5854  -25.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5843  -26.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2991  -26.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2974  -25.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0127  -25.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0115  -26.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7284  -26.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7308  -25.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4522  -25.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4489  -26.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2384  -26.6350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.7297  -25.9644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2437  -25.2902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.7274  -27.6150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.7308  -24.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.5547  -25.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4902  -27.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5017  -24.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2964  -27.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5482  -28.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3545  -28.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6063  -29.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3094  -24.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5674  -23.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3750  -23.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6331  -22.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4407  -22.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4126  -29.5161    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
 14 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 23 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: 381.54

Molecular Weight (Monoisotopic): 381.2537

AlogP: 5.02

#Rotatable Bonds: 10

Polar Surface Area: 42.95

Molecular Species: ┄

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.38

CX LogD: 1.38

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.37

Np Likeness Score: -0.03

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