(E)-2-(2-(1H-indol-2-yl)vinyl)-1-methyl-4-(4-methylpiperidin-1-yl)quinolin-1-ium iodide

ID: ALA4547564

PubChem CID: 155553719

Max Phase: Preclinical

Molecular Formula: C26H28IN3

Molecular Weight: 382.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1CCN(c2cc(/C=C/c3cc4ccccc4[nH]3)[n+](C)c3ccccc23)CC1.[I-]

Standard InChI:  InChI=1S/C26H27N3.HI/c1-19-13-15-29(16-14-19)26-18-22(28(2)25-10-6-4-8-23(25)26)12-11-21-17-20-7-3-5-9-24(20)27-21;/h3-12,17-19H,13-16H2,1-2H3;1H

Standard InChI Key:  IHHCMHBBQCAHBP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   20.6568   -5.9886    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   19.3594   -4.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3583   -4.9839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0663   -5.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0645   -3.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7731   -4.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7739   -4.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4824   -5.3868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1907   -4.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1860   -4.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4769   -3.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4841   -6.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9000   -5.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6061   -4.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3154   -5.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4067   -6.1863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0633   -5.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6125   -5.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2081   -6.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6177   -7.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4317   -7.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8342   -6.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4223   -5.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4725   -2.9333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1824   -2.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1801   -1.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4720   -1.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7646   -1.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7654   -2.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4707   -0.4846    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
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  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: 382.53

Molecular Weight (Monoisotopic): 382.2278

AlogP: 5.55

#Rotatable Bonds: 3

Polar Surface Area: 22.91

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.20

CX LogD: 1.20

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -0.32

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