2-Methyl-1,3-dioctyl-4,9-dioxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-ium bromide

ID: ALA4858055

PubChem CID: 164610381

Max Phase: Preclinical

Molecular Formula: C28H41BrN2O2

Molecular Weight: 437.65

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCn1c2c([n+](CCCCCCCC)c1C)C(=O)c1ccccc1C2=O.[Br-]

Standard InChI:  InChI=1S/C28H41N2O2.BrH/c1-4-6-8-10-12-16-20-29-22(3)30(21-17-13-11-9-7-5-2)26-25(29)27(31)23-18-14-15-19-24(23)28(26)32;/h14-15,18-19H,4-13,16-17,20-21H2,1-3H3;1H/q+1;/p-1

Standard InChI Key:  LDBWINBGAGIDKC-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
   16.1121   -5.3602    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.2192   -5.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2181   -6.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9329   -6.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9311   -5.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6465   -5.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6453   -6.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3622   -6.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3646   -5.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0860   -5.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0827   -6.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8723   -6.8061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3635   -6.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8775   -5.4613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3612   -7.7862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3646   -4.4701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1885   -6.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1240   -7.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1355   -4.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9303   -7.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1820   -8.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9884   -8.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2401   -9.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9432   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2012   -3.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0089   -3.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2669   -2.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0745   -2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0465   -9.6873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3326   -1.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1402   -1.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2982  -10.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1045  -10.6476    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
 22 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 23 29  1  0
 28 30  1  0
 30 31  1  0
 29 32  1  0
 32 33  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: 437.65

Molecular Weight (Monoisotopic): 437.3163

AlogP: 6.58

#Rotatable Bonds: 14

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: 3.16

CX LogD: 3.16

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.21

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