(E)-2-(2-(1H-indol-2-yl)vinyl)-1-methyl-4-((2-(piperidin-1-yl)ethyl)amino)quinolin-1-ium iodide

ID: ALA4560032

PubChem CID: 155510491

Max Phase: Preclinical

Molecular Formula: C27H31IN4

Molecular Weight: 411.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[n+]1c(/C=C/c2cc3ccccc3[nH]2)cc(NCCN2CCCCC2)c2ccccc21.[I-]

Standard InChI:  InChI=1S/C27H30N4.HI/c1-30-23(14-13-22-19-21-9-3-5-11-25(21)29-22)20-26(24-10-4-6-12-27(24)30)28-15-18-31-16-7-2-8-17-31;/h3-6,9-14,19-20H,2,7-8,15-18H2,1H3,(H,28,29);1H

Standard InChI Key:  FNLPKEUBCJPPMF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   12.7408  -13.9005    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   11.4434  -12.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4422  -12.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1503  -13.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1485  -11.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8571  -12.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8579  -12.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5664  -13.2987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2747  -12.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2699  -12.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5608  -11.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5681  -14.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9840  -13.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6901  -12.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3994  -13.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4907  -14.0982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473  -12.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6965  -13.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2921  -14.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7017  -14.9637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5156  -14.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9182  -14.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5062  -13.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5565  -10.8452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2620  -10.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9719  -10.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6774  -10.4254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3820  -10.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0855  -10.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0853   -9.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3756   -9.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6660   -9.6094    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
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  8 12  1  0
  9 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 19  1  0
 18 17  1  0
 17 15  2  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 11 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  CHG  2   1  -1   8   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: 411.57

Molecular Weight (Monoisotopic): 411.2543

AlogP: 5.21

#Rotatable Bonds: 6

Polar Surface Area: 34.94

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.83

CX LogP: 0.30

CX LogD: -1.14

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -0.64

References

1. Cai S, Yuan W, Li Y, Huang X, Guo Q, Tang Z, Fang Z, Lin H, Wong WL, Wong KY, Lu YJ, Sun N..  (2019)  Antibacterial activity of indolyl-quinolinium derivatives and study their mode of action.,  27  (7): [PMID:30792100] [10.1016/j.bmc.2019.02.024]

Source

Source(1):

• Scientific Literature