3-(sec-Butyl)-2-methyl-4,9-dioxo-1-propyl-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-ium bromide

ID: ALA4858235

PubChem CID: 164612479

Max Phase: Preclinical

Molecular Formula: C19H23BrN2O2

Molecular Weight: 311.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCn1c2c([n+](C(C)CC)c1C)C(=O)c1ccccc1C2=O.[Br-]

Standard InChI:  InChI=1S/C19H23N2O2.BrH/c1-5-11-20-13(4)21(12(3)6-2)17-16(20)18(22)14-9-7-8-10-15(14)19(17)23;/h7-10,12H,5-6,11H2,1-4H3;1H/q+1;/p-1

Standard InChI Key:  ATIQHRISMBSYHD-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   44.1112   -5.7070    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   37.4882   -5.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4870   -6.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2018   -6.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2000   -4.8828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9154   -5.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9142   -6.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6310   -6.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6334   -4.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3549   -5.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3516   -6.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1410   -6.3851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.6322   -5.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1464   -5.0403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6300   -7.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.6334   -4.0491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4572   -5.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3928   -7.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4044   -4.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2120   -4.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4699   -3.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8548   -3.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1991   -7.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4508   -8.1310    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
 19 20  1  0
 20 21  1  0
 19 22  1  0
 18 23  1  0
 23 24  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: 311.41

Molecular Weight (Monoisotopic): 311.1754

AlogP: 3.24

#Rotatable Bonds: 4

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: -0.87

CX LogD: -0.87

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.69

Np Likeness Score: -0.15

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