3,3'-(1,3-Phenylenebis(butane-4,1-diyl))bis(5-(2-methoxyethyl)-4-methylthiazol-3-ium)Chloride

ID: ALA2314633

PubChem CID: 71520654

Max Phase: Preclinical

Molecular Formula: C28H42Cl2N2O2S2

Molecular Weight: 502.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCc1sc[n+](CCCCc2cccc(CCCC[n+]3csc(CCOC)c3C)c2)c1C.[Cl-].[Cl-]

Standard InChI:  InChI=1S/C28H42N2O2S2.2ClH/c1-23-27(14-18-31-3)33-21-29(23)16-7-5-10-25-12-9-13-26(20-25)11-6-8-17-30-22-34-28(24(30)2)15-19-32-4;;/h9,12-13,20-22H,5-8,10-11,14-19H2,1-4H3;2*1H/q+2;;/p-2

Standard InChI Key:  FHFWYNQHLZEASZ-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 36 36  0  0  0  0  0  0  0  0999 V2000
    2.2500   -7.6582    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.0242   -8.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3628   -8.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6869   -8.8570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9327   -9.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7556   -9.6553    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7422   -8.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7450   -7.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4610   -7.2301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4638   -6.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3749   -7.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5951   -8.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2912   -8.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0226   -8.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8644   -8.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7276   -7.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7223   -8.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4338   -8.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1513   -8.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1527   -7.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4406   -7.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0624   -9.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8874   -9.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1449   -8.6693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4749   -8.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8109   -8.6693    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8613   -8.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738   -8.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417  -10.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0471  -10.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6275  -11.5954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0330  -12.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3714  -10.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2902   -8.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0027   -8.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3040   -7.6248    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  1  0
 13 14  1  0
 14  4  1  0
 15 12  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 22  1  0
 24 27  1  0
 27 28  1  0
 22 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 23 33  1  0
 28 34  1  0
 34 35  1  0
 35 17  1  0
 19 15  1  0
M  CHG  4   1  -1   4   1  24   1  36  -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: 502.79

Molecular Weight (Monoisotopic): 502.2677

AlogP: 5.43

#Rotatable Bonds: 16

Polar Surface Area: 26.22

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -1.04

CX LogD: -1.04

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.19

Np Likeness Score: -0.11

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