3-(3-(1-(2-(3,4-Dimethylthiazol-3-ium-5-yl)ethyl)-1H-1,2,3-triazol-4-yl)propyl)-5-(2-methoxyethyl)-4-methylthiazol-3-ium Chloride

ID: ALA2314645

PubChem CID: 71520834

Max Phase: Preclinical

Molecular Formula: C19H29Cl2N5OS2

Molecular Weight: 407.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCc1sc[n+](CCCc2cn(CCc3sc[n+](C)c3C)nn2)c1C.[Cl-].[Cl-]

Standard InChI:  InChI=1S/C19H29N5OS2.2ClH/c1-15-18(26-13-22(15)3)7-10-24-12-17(20-21-24)6-5-9-23-14-27-19(16(23)2)8-11-25-4;;/h12-14H,5-11H2,1-4H3;2*1H/q+2;;/p-2

Standard InChI Key:  QTZCYEVZWUOYMP-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   22.9829  -14.5288    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.9622  -15.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7872  -15.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0444  -14.2361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3747  -13.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7097  -14.2365    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.2714  -15.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5547  -15.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7298  -15.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3223  -16.4606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7926  -13.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4677  -14.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2158  -14.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8910  -14.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9057  -15.3127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6943  -15.5549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1686  -14.8799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6729  -14.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9935  -14.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4174  -15.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2423  -15.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7398  -16.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5202  -15.9502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5069  -15.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7184  -14.8831    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.4991  -17.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1953  -16.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4973  -16.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2414  -12.2789    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
  3  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 14  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  1  0
 22 26  1  0
 23 27  1  0
 10 28  1  0
M  CHG  4   1  -1   4   1  23   1  29  -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: 407.61

Molecular Weight (Monoisotopic): 407.1803

AlogP: 2.19

#Rotatable Bonds: 10

Polar Surface Area: 47.70

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.48

CX LogP: -4.62

CX LogD: -4.62

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: -0.87

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