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

ID: ALA2311570

PubChem CID: 46934863

Max Phase: Preclinical

Molecular Formula: C26H38Cl2N2O2S2

Molecular Weight: 474.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CCO)sc[n+]1CCCCc1ccc(CCCC[n+]2csc(CCO)c2C)cc1.[Cl-].[Cl-]

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

Standard InChI Key:  JLJBFTFKNHGDIH-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 34 34  0  0  0  0  0  0  0  0999 V2000
   10.4290   -2.5624    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.0736   -4.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0840   -3.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3027   -3.3804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8079   -4.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2853   -4.7142    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.8523   -4.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4822   -4.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2585   -4.4995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7583   -3.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5941   -1.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5912   -2.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3041   -2.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7401   -1.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7348   -2.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4463   -2.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1638   -2.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1652   -1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4530   -0.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0750   -3.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000   -3.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1574   -2.5361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234   -2.5361    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8739   -2.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5863   -2.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542   -4.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0595   -4.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6400   -5.4621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -3.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3028   -2.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152   -2.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8803   -0.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -1.0334    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  1  0
 12 13  1  0
 13  4  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
 22 25  1  0
 25 26  1  0
 20 27  1  0
 27 28  1  0
 28 29  1  0
 21 30  1  0
 26 31  1  0
 31 32  1  0
 32 15  1  0
 18 33  1  0
 33 11  1  0
M  CHG  4   1  -1   4   1  22   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: 4.12

#Rotatable Bonds: 14

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: -2.33

CX LogD: -2.33

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.27

Np Likeness Score: 0.09

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