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

ID: ALA2314630

PubChem CID: 71720396

Max Phase: Preclinical

Molecular Formula: C24H34Cl2N2O2S2

Molecular Weight: 446.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CCO)sc[n+]1CCCc1ccc(CCC[n+]2csc(CCO)c2C)cc1.[Cl-].[Cl-]

Standard InChI:  InChI=1S/C24H34N2O2S2.2ClH/c1-19-23(11-15-27)29-17-25(19)13-3-5-21-7-9-22(10-8-21)6-4-14-26-18-30-24(12-16-28)20(26)2;;/h7-10,17-18,27-28H,3-6,11-16H2,1-2H3;2*1H/q+2;;/p-2

Standard InChI Key:  OLALZBRYVFPYFL-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 32 32  0  0  0  0  0  0  0  0999 V2000
    8.3374  -27.8078    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.3438  -30.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3541  -29.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5729  -28.9224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0781  -29.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5555  -30.2562    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1225  -30.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7523  -29.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5287  -30.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0285  -28.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874  -26.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6124  -26.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8699  -25.5982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999  -25.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5359  -25.5982    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5863  -25.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2988  -25.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667  -27.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7721  -27.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3525  -28.5242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964  -27.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152  -25.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7277  -25.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7222  -26.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4338  -26.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1513  -26.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1527  -25.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4405  -25.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8643  -26.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8613  -27.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5744  -28.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750  -24.4371    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
  3 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
 13 16  1  0
 16 17  1  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 12 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 31  4  1  0
M  CHG  4   1  -1   4   1  13   1  32  -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: 446.68

Molecular Weight (Monoisotopic): 446.2051

AlogP: 3.34

#Rotatable Bonds: 12

Polar Surface Area: 48.22

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -3.22

CX LogD: -3.22

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: 0.08

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