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

ID: ALA2314641

PubChem CID: 71521472

Max Phase: Preclinical

Molecular Formula: C26H30Br2N2O2S2

Molecular Weight: 466.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCc1sc[n+](CC#Cc2ccc(C#CC[n+]3csc(CCOC)c3C)cc2)c1C.[Br-].[Br-]

Standard InChI:  InChI=1S/C26H30N2O2S2.2BrH/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,13-18H2,1-4H3;2*1H/q+2;;/p-2

Standard InChI Key:  ZEEZZKUWWBZLON-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 34 34  0  0  0  0  0  0  0  0999 V2000
   12.6089  -30.5397    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   20.6214  -28.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8965  -28.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2958  -29.0348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6518  -29.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4668  -29.6719    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.2600  -28.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1247  -27.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7614  -27.0005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7907  -27.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5697  -28.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7534  -31.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2895  -31.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0529  -31.5330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9871  -30.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1867  -30.5195    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.8288  -31.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9288  -31.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5706  -32.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7484  -32.0856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0961  -32.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9284  -30.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2024  -31.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6357  -31.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6655  -29.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9429  -29.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3791  -29.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3583  -30.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4791  -31.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1018  -29.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8190  -29.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3902  -32.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5334  -27.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2549  -27.8246    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
 20 32  1  0
  9 33  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: 466.67

Molecular Weight (Monoisotopic): 466.1738

AlogP: 3.48

#Rotatable Bonds: 8

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: -2.45

CX LogD: -2.45

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.38

Np Likeness Score: -0.20

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