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

ID: ALA4857689

PubChem CID: 164615849

Max Phase: Preclinical

Molecular Formula: C22H27BrN2O2

Molecular Weight: 351.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCn1c2c([n+](C3CCCCC3)c1C)C(=O)c1ccccc1C2=O.[Br-]

Standard InChI:  InChI=1S/C22H27N2O2.BrH/c1-3-4-14-23-15(2)24(16-10-6-5-7-11-16)20-19(23)21(25)17-12-8-9-13-18(17)22(20)26;/h8-9,12-13,16H,3-7,10-11,14H2,1-2H3;1H/q+1;/p-1

Standard InChI Key:  VPOTZJIVFGGKME-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   44.2058   -9.5853    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   37.9530   -9.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9519  -10.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6663  -11.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6645   -9.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3796   -9.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3785  -10.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0951  -11.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0974   -9.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8186   -9.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8153  -10.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6044  -10.9182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.0955  -10.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6097   -9.5739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.0940  -11.8978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0975   -8.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.9202  -10.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8562  -11.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8677   -8.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6621  -11.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9137  -12.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7197  -12.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6739   -8.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9325   -7.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3861   -7.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5774   -7.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3152   -8.1811    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
 19 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  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: 351.47

Molecular Weight (Monoisotopic): 351.2067

AlogP: 4.16

#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: 0.08

CX LogD: 0.08

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.66

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