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

ID: ALA2314646

PubChem CID: 71520836

Max Phase: Preclinical

Molecular Formula: C25H33Cl2N5OS2

Molecular Weight: 483.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCc1sc[n+](CCCc2cn(CCc3sc[n+](Cc4ccccc4)c3C)nn2)c1C.[Cl-].[Cl-]

Standard InChI:  InChI=1S/C25H33N5OS2.2ClH/c1-20-25(12-15-31-3)32-18-28(20)13-7-10-23-17-30(27-26-23)14-11-24-21(2)29(19-33-24)16-22-8-5-4-6-9-22;;/h4-6,8-9,17-19H,7,10-16H2,1-3H3;2*1H/q+2;;/p-2

Standard InChI Key:  JCIPWVDFJAVUGF-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
   13.2090  -18.7509    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.6049  -20.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4299  -20.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6872  -19.3707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0174  -18.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3524  -19.3710    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.9142  -20.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1974  -20.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3724  -20.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9649  -21.5953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4354  -19.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1105  -19.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8589  -19.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5340  -19.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5487  -20.4473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3374  -20.6897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8116  -20.0145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3160  -19.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6366  -20.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0605  -20.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8855  -20.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3830  -21.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1635  -21.0849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1502  -20.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3616  -20.0178    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.1423  -22.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1398  -21.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8387  -21.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8305  -22.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1128  -22.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1042  -23.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8118  -24.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5295  -23.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5347  -22.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5803  -19.2177    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
 10 27  1  0
 23 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
M  CHG  4   1  -1   4   1  23   1  35  -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: 483.71

Molecular Weight (Monoisotopic): 483.2116

AlogP: 3.71

#Rotatable Bonds: 12

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: -2.89

CX LogD: -2.89

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.29

Np Likeness Score: -0.84

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