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

ID: ALA4878104

PubChem CID: 164626874

Max Phase: Preclinical

Molecular Formula: C23H29BrN2O2

Molecular Weight: 365.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCn1c2c([n+](CC3CCCCC3)c1C)C(=O)c1ccccc1C2=O.[Br-]

Standard InChI:  InChI=1S/C23H29N2O2.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;/h8-9,12-13,17H,3-7,10-11,14-15H2,1-2H3;1H/q+1;/p-1

Standard InChI Key:  ADZKEAHOYKWOME-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   15.8598  -16.5220    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.1400  -16.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1389  -17.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8537  -17.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8519  -15.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5673  -16.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5661  -17.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2830  -17.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2853  -15.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0068  -16.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0035  -17.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7930  -17.4768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2843  -16.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7983  -16.1320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2820  -18.4569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2854  -15.1407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1093  -16.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0448  -18.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0563  -15.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8511  -18.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1028  -19.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9091  -19.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8629  -15.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4049  -15.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2083  -15.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4741  -14.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9302  -14.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1204  -14.4043    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
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  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: 365.50

Molecular Weight (Monoisotopic): 365.2224

AlogP: 4.24

#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: 0.39

CX LogD: 0.39

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.63

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