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

ID: ALA4856889

PubChem CID: 164609763

Max Phase: Preclinical

Molecular Formula: C23H23BrN2O2

Molecular Weight: 359.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCn1c2c([n+](Cc3ccccc3)c1C)C(=O)c1ccccc1C2=O.[Br-]

Standard InChI:  InChI=1S/C23H23N2O2.BrH/c1-3-4-14-24-16(2)25(15-17-10-6-5-7-11-17)21-20(24)22(26)18-12-8-9-13-19(18)23(21)27;/h5-13H,3-4,14-15H2,1-2H3;1H/q+1;/p-1

Standard InChI Key:  MCYUQQBZAQSNFU-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   31.4675  -17.5940    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   24.7939  -17.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7928  -18.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5076  -18.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5058  -16.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2212  -17.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2200  -18.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9369  -18.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9392  -16.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6607  -17.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6574  -18.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4468  -18.2642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9382  -17.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4522  -16.9194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9359  -19.2443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9393  -15.9283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7632  -17.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6987  -19.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7102  -16.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5049  -19.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7567  -20.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5630  -20.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5167  -15.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0584  -16.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8642  -16.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1267  -15.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5771  -15.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7734  -15.1949    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  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  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: 359.45

Molecular Weight (Monoisotopic): 359.1754

AlogP: 3.71

#Rotatable Bonds: 5

Polar Surface Area: 42.95

Molecular Species: ┄

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.00

CX LogD: 0.00

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -0.19

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