5-(2-(4-((2-(3,4-Dimethylthiazol-3-ium-5-yl)ethoxy)methyl)-1H-1,2,3-triazol-1-yl)ethyl)-3,4-dimethylthiazol-3-ium Chloride

ID: ALA2314643

PubChem CID: 71520737

Max Phase: Preclinical

Molecular Formula: C17H25Cl2N5OS2

Molecular Weight: 379.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CCOCc2cn(CCc3sc[n+](C)c3C)nn2)sc[n+]1C.[Cl-].[Cl-]

Standard InChI:  InChI=1S/C17H25N5OS2.2ClH/c1-13-16(24-11-20(13)3)5-7-22-9-15(18-19-22)10-23-8-6-17-14(2)21(4)12-25-17;;/h9,11-12H,5-8,10H2,1-4H3;2*1H/q+2;;/p-2

Standard InChI Key:  AKTOKLYDIYBEEK-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 27 27  0  0  0  0  0  0  0  0999 V2000
   15.8332   -6.7791    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.9249   -7.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7498   -7.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0066   -6.7200    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.3374   -6.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6723   -6.7200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4391   -8.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1716   -8.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9966   -8.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4184   -8.9118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2434   -8.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7350   -9.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4888  -10.3485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1611  -10.8266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8240  -10.3340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5607   -9.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6489  -10.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0477  -11.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8725  -11.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3436  -11.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1330  -11.5225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1487  -10.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3691  -10.4278    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.0739  -12.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8876   -6.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7910  -12.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9206  -10.0666    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  1  0
  5  6  2  0
  6  2  1  0
  2  7  1  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  1  0
 20 24  1  0
  6 25  1  0
 21 26  1  0
M  CHG  4   1  -1   6   1  21   1  27  -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: 379.56

Molecular Weight (Monoisotopic): 379.1490

AlogP: 1.67

#Rotatable Bonds: 8

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: ┄

CX LogP: -5.14

CX LogD: -5.14

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.44

Np Likeness Score: -1.12

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