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

ID: ALA2314642

PubChem CID: 71520735

Max Phase: Preclinical

Molecular Formula: C26H30Br2N2O2S2

Molecular Weight: 466.67

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H30N2O2S2.2BrH/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,5-6,13-18H2,1-2H3;2*1H/q+2;;/p-2

Standard InChI Key:  AJISVNQOEKVRCM-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 34 34  0  0  0  0  0  0  0  0999 V2000
   10.1157   -1.9707    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.0591   -1.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2457   -1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1254   -2.1629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8682   -2.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4399   -1.9361    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.2342   -0.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6234    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7974    0.9682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6553   -0.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6473   -6.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4698   -6.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667   -5.2747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617   -4.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367   -5.3763    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2101   -6.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5987   -7.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1628   -8.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -6.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6969   -2.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9528   -5.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0537   -4.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3272   -4.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7614   -4.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7911   -2.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0681   -3.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5051   -3.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4843   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6037   -4.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2282   -2.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9458   -2.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3176   -4.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4041   -2.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665   -3.5955    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 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 12 19  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 21  1  0
 27 30  1  0
 30 31  3  0
 31 20  1  0
 21 32  1  0
 32 13  1  0
 20 33  1  0
 33  4  1  0
M  CHG  4   1  -1   4   1  13   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: 2.95

#Rotatable Bonds: 8

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: 10.82

CX Basic pKa: ┄

CX LogP: -3.16

CX LogD: -3.16

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: 0.02

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