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

ID: ALA4857216

PubChem CID: 164614164

Max Phase: Preclinical

Molecular Formula: C20H25BrN2O2

Molecular Weight: 325.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(C)[n+]1c2c(n(CC(C)C)c1C)C(=O)c1ccccc1C2=O.[Br-]

Standard InChI:  InChI=1S/C20H25N2O2.BrH/c1-6-13(4)22-14(5)21(11-12(2)3)17-18(22)20(24)16-10-8-7-9-15(16)19(17)23;/h7-10,12-13H,6,11H2,1-5H3;1H/q+1;/p-1

Standard InChI Key:  MLAMUVDSPOQLMT-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   34.6520  -14.6302    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   28.1643  -14.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1632  -15.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8779  -15.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8762  -14.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5915  -14.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5903  -15.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3072  -15.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3096  -13.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0310  -14.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0278  -15.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8172  -15.5099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3085  -14.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8225  -14.1651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3062  -16.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3096  -13.1740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1334  -14.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0690  -16.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0805  -13.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8881  -13.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1462  -12.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5309  -12.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8752  -16.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1271  -17.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4297  -15.8594    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
 23 25  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: 325.43

Molecular Weight (Monoisotopic): 325.1911

AlogP: 3.49

#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: -0.51

CX LogD: -0.51

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.69

Np Likeness Score: -0.14

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