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

ID: ALA4877597

PubChem CID: 164626027

Max Phase: Preclinical

Molecular Formula: C18H21BrN2O2

Molecular Weight: 297.38

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H21N2O2.BrH/c1-5-11(3)20-12(4)19(6-2)15-16(20)18(22)14-10-8-7-9-13(14)17(15)21;/h7-11H,5-6H2,1-4H3;1H/q+1;/p-1

Standard InChI Key:  UPKZMXNWGBOIEX-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   34.0530   -5.2341    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   27.7368   -5.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7355   -6.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4503   -6.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4485   -4.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1638   -5.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1626   -6.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8794   -6.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8818   -4.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6031   -5.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5999   -6.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3893   -6.2930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8805   -5.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3946   -4.9483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8784   -7.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8818   -3.9572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7054   -5.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6410   -7.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6525   -4.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4601   -3.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7181   -3.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1030   -3.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0866   -7.6893    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
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: 297.38

Molecular Weight (Monoisotopic): 297.1598

AlogP: 2.85

#Rotatable Bonds: 3

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: -1.39

CX LogD: -1.39

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.70

Np Likeness Score: -0.08

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