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

ID: ALA4858484

PubChem CID: 164614223

Max Phase: Preclinical

Molecular Formula: C26H37BrN2O2

Molecular Weight: 409.59

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCn1c2c([n+](C(C)CC)c1C)C(=O)c1ccccc1C2=O.[Br-]

Standard InChI:  InChI=1S/C26H37N2O2.BrH/c1-5-7-8-9-10-11-12-15-18-27-20(4)28(19(3)6-2)24-23(27)25(29)21-16-13-14-17-22(21)26(24)30;/h13-14,16-17,19H,5-12,15,18H2,1-4H3;1H/q+1;/p-1

Standard InChI Key:  CDHXNOHUJHJTCI-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   14.3149  -22.9857    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.4232  -22.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4221  -23.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1369  -23.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1350  -22.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8504  -22.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8493  -23.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5660  -23.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684  -22.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2899  -22.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2866  -23.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0760  -23.6635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5674  -22.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0814  -22.3188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5651  -24.6436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5685  -21.3275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3922  -22.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3278  -24.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3394  -21.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1470  -21.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4051  -20.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7898  -20.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1341  -24.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3859  -25.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1922  -25.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4440  -26.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2501  -26.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5019  -27.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3082  -27.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5600  -28.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3663  -28.4653    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
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  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: 409.59

Molecular Weight (Monoisotopic): 409.2850

AlogP: 5.97

#Rotatable Bonds: 11

Polar Surface Area: 42.95

Molecular Species: ┄

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.24

CX LogD: 2.24

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.29

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