1-(14-bromotetradecyl)-4-(2-(8-hydroxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)vinyl)pyridinium bromide

ID: ALA4873996

PubChem CID: 164627843

Max Phase: Preclinical

Molecular Formula: C33H48Br2N2O

Molecular Weight: 568.66

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Oc1c(/C=C/c2cc[n+](CCCCCCCCCCCCCCBr)cc2)cc2c3c1CCCN3CCC2.[Br-]

Standard InChI:  InChI=1S/C33H47BrN2O.BrH/c34-21-11-9-7-5-3-1-2-4-6-8-10-12-22-35-25-19-28(20-26-35)17-18-30-27-29-15-13-23-36-24-14-16-31(32(29)36)33(30)37;/h17-20,25-27H,1-16,21-24H2;1H

Standard InChI Key:  TXFSQKCQQRHBJC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 38 40  0  0  0  0  0  0  0  0999 V2000
   12.2572  -21.3518    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.4339  -20.4913    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1469  -20.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8628  -20.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5758  -20.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2918  -20.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0047  -20.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7208  -20.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4337  -20.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1498  -20.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8626  -20.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5787  -20.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2916  -20.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0077  -20.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7205  -20.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4366  -20.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1495  -20.0384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8650  -20.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5774  -20.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5747  -19.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8537  -18.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1442  -19.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2871  -18.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2829  -17.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9953  -17.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7097  -17.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9874  -16.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2691  -16.3245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4211  -17.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1369  -17.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8542  -17.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8510  -16.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4222  -16.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1306  -16.3016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1225  -15.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4077  -15.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6993  -15.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7058  -16.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 29  1  0
 38 27  2  0
 27 25  1  0
 27 28  1  0
 33 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 34  1  0
 33 34  1  0
 33 38  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
M  CHG  2   1  -1  17   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: 568.66

Molecular Weight (Monoisotopic): 567.2945

AlogP: 8.63

#Rotatable Bonds: 16

Polar Surface Area: 27.35

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.02

CX Basic pKa: 4.10

CX LogP: 5.80

CX LogD: 5.80

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.12

Np Likeness Score: 0.00

References

1. Cueto-Díaz EJ, Ebiloma GU, Alfayez IA, Ungogo MA, Lemgruber L, González-García MC, Giron MD, Salto R, Fueyo-González FJ, Shiba T, González-Vera JA, Ruedas Rama MJ, Orte A, de Koning HP, Dardonville C..  (2021)  Synthesis, biological, and photophysical studies of molecular rotor-based fluorescent inhibitors of the trypanosome alternative oxidase.,  220  [PMID:33940464] [10.1016/j.ejmech.2021.113470]

Source

Source(1):

• Scientific Literature