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

ID: ALA4878535

PubChem CID: 164625847

Max Phase: Preclinical

Molecular Formula: C19H21BrN2O2

Molecular Weight: 309.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(C)[n+]1c2c(n(C3CC3)c1C)C(=O)c1ccccc1C2=O.[Br-]

Standard InChI:  InChI=1S/C19H21N2O2.BrH/c1-4-11(2)20-12(3)21(13-9-10-13)17-16(20)18(22)14-7-5-6-8-15(14)19(17)23;/h5-8,11,13H,4,9-10H2,1-3H3;1H/q+1;/p-1

Standard InChI Key:  SKAYMTNRMGCFIH-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   17.2472  -15.1031    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.1066  -14.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1054  -15.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8202  -16.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8184  -14.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5337  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5325  -15.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2494  -16.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2518  -14.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9732  -14.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9700  -15.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7594  -15.9433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2507  -15.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7648  -14.5984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2484  -16.9232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2518  -13.6073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0756  -15.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0112  -16.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0228  -13.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8304  -13.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0884  -12.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4731  -13.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8375  -17.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6231  -17.2797    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
 23 18  1  0
 24 23  1  0
 18 24  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: 309.39

Molecular Weight (Monoisotopic): 309.1598

AlogP: 3.17

#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: -1.28

CX LogD: -1.28

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: -0.06

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