3-Butyl-2-ethyl-1-octyl-4,9-dioxo-1H,4H,9H-naphtho[2,3-d]imidazole-3-ium bromide

ID: ALA4859558

PubChem CID: 164613746

Max Phase: Preclinical

Molecular Formula: C25H35BrN2O2

Molecular Weight: 395.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCC[n+]1c2c(n(CCCC)c1CC)C(=O)c1ccccc1C2=O.[Br-]

Standard InChI:  InChI=1S/C25H35N2O2.BrH/c1-4-7-9-10-11-14-18-27-21(6-3)26(17-8-5-2)22-23(27)25(29)20-16-13-12-15-19(20)24(22)28;/h12-13,15-16H,4-11,14,17-18H2,1-3H3;1H/q+1;/p-1

Standard InChI Key:  FHNDNDTZIVGRQN-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   31.7197  -24.8460    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   25.6522  -25.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6511  -26.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3659  -26.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3641  -24.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0795  -25.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0783  -26.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7952  -26.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7975  -24.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5190  -25.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5157  -26.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3052  -26.3225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7965  -25.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3105  -24.9777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7942  -27.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7976  -23.9864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6215  -25.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5570  -27.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5685  -24.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3632  -27.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6150  -28.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4213  -28.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3741  -24.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6329  -23.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0311  -26.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4409  -23.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7008  -22.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5088  -22.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7688  -21.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5768  -21.1814    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
 19 23  1  0
 23 24  1  0
 17 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  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: 395.57

Molecular Weight (Monoisotopic): 395.2693

AlogP: 5.27

#Rotatable Bonds: 11

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: 2.08

CX LogD: 2.08

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: -0.01

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