3,3'-(1,4-Phenylenebis(prop-2-yne-3,1-diyl))bis(5-(2-hydroxyethyl)-4-methylthiazol-3-ium)Bromide

ID: ALA2314640

PubChem CID: 71521381

Max Phase: Preclinical

Molecular Formula: C24H26Br2N2O2S2

Molecular Weight: 438.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CCO)sc[n+]1CC#Cc1ccc(C#CC[n+]2csc(CCO)c2C)cc1.[Br-].[Br-]

Standard InChI:  InChI=1S/C24H26N2O2S2.2BrH/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,11-16H2,1-2H3;2*1H/q+2;;/p-2

Standard InChI Key:  HEUBVICFUQYPTQ-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 32 32  0  0  0  0  0  0  0  0999 V2000
   20.1903  -23.7005    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   21.9273  -24.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2026  -24.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6018  -24.5983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9577  -25.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7728  -25.2353    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.5659  -23.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4306  -23.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0673  -22.5641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0967  -23.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8757  -24.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0600  -26.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5961  -27.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3594  -27.0961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2937  -26.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4934  -26.0827    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.1352  -27.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2354  -26.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8773  -27.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0551  -27.6485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4027  -28.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2348  -26.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5088  -26.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9421  -26.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9717  -24.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2492  -25.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6853  -25.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6645  -26.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7856  -27.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4081  -25.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1252  -24.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7614  -25.3243    0.0000 Br  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  4  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
 12 18  1  0
 18 19  1  0
 19 20  1  0
 13 21  1  0
 23 22  1  0
 22 24  2  0
 24 28  1  0
 27 25  1  0
 25 26  2  0
 26 22  1  0
 27 28  2  0
 23 29  3  0
 29 17  1  0
 27 30  1  0
 30 31  3  0
 31 11  1  0
M  CHG  4   1  -1   4   1  14   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: 438.62

Molecular Weight (Monoisotopic): 438.1425

AlogP: 2.17

#Rotatable Bonds: 6

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: -3.74

CX LogD: -3.74

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: 0.00

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