3,3'-(3,3'-(1,4-phenylene)bis(propane-3,1-diyl))bis(5-(2-methoxyethyl)-4-methylthiazol-3-ium)chloride

ID: ALA2314631

PubChem CID: 71717358

Max Phase: Preclinical

Molecular Formula: C26H38Cl2N2O2S2

Molecular Weight: 474.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCc1sc[n+](CCCc2ccc(CCC[n+]3csc(CCOC)c3C)cc2)c1C.[Cl-].[Cl-]

Standard InChI:  InChI=1S/C26H38N2O2S2.2ClH/c1-21-25(13-17-29-3)31-19-27(21)15-5-7-23-9-11-24(12-10-23)8-6-16-28-20-32-26(22(28)2)14-18-30-4;;/h9-12,19-20H,5-8,13-18H2,1-4H3;2*1H/q+2;;/p-2

Standard InChI Key:  CNWFEHKDLUHJRK-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 34 34  0  0  0  0  0  0  0  0999 V2000
   15.7372  -24.5579    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.1311  -30.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1414  -29.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3601  -28.9432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8653  -29.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3428  -30.2771    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.9098  -30.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5396  -29.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3159  -30.0622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9458  -29.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8158  -28.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5747  -26.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3997  -26.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6571  -25.6191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9872  -25.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3231  -25.6190    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.3736  -25.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0860  -25.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1539  -27.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5594  -27.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1398  -28.5451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5452  -29.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8837  -27.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8025  -25.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5149  -25.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5095  -26.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2211  -26.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9386  -26.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9400  -25.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2278  -25.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6515  -26.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6486  -27.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3616  -28.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0455  -27.8078    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  2  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  3 11  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  1  0
 14 17  1  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 13 23  1  0
 18 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33  4  1  0
M  CHG  4   1  -1   4   1  14   1  34  -1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 474.74

Molecular Weight (Monoisotopic): 474.2364

AlogP: 4.64

#Rotatable Bonds: 14

Polar Surface Area: 26.22

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -1.93

CX LogD: -1.93

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: -0.12

References

1. Caldarelli SA, El Fangour S, Wein S, Tran van Ba C, Périgaud C, Pellet A, Vial HJ, Peyrottes S..  (2013)  New bis-thiazolium analogues as potential antimalarial agents: design, synthesis, and biological evaluation.,  56  (2): [PMID:23289711] [10.1021/jm3014585]

Source

Source(1):

• Scientific Literature