3-Benzyl-5-(2-(4-((2-(3-benzyl-4-methylthiazol-3-ium-5-yl)-ethoxy)methyl)-1H-1,2,3-triazol-1-yl)ethyl)-4-methylthiazol-3-iumBromide

ID: ALA2314644

PubChem CID: 71717954

Max Phase: Preclinical

Molecular Formula: C29H33Br2N5OS2

Molecular Weight: 531.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CCOCc2cn(CCc3sc[n+](Cc4ccccc4)c3C)nn2)sc[n+]1Cc1ccccc1.[Br-].[Br-]

Standard InChI:  InChI=1S/C29H33N5OS2.2BrH/c1-23-28(36-21-32(23)17-25-9-5-3-6-10-25)13-15-34-19-27(30-31-34)20-35-16-14-29-24(2)33(22-37-29)18-26-11-7-4-8-12-26;;/h3-12,19,21-22H,13-18,20H2,1-2H3;2*1H/q+2;;/p-2

Standard InChI Key:  YNPLEEPYZURNLW-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 39 41  0  0  0  0  0  0  0  0999 V2000
   10.7418  -18.7502    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.9625  -15.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875  -15.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0444  -14.9202    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3750  -14.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092  -14.9205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4767  -16.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093  -16.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342  -16.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4560  -17.1121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2811  -17.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7727  -17.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5266  -18.5488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1989  -19.0270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8617  -18.5344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5985  -17.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6867  -18.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0854  -19.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9103  -19.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3814  -19.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1710  -19.7224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1866  -18.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4070  -18.6282    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1118  -20.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015  -14.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0149  -13.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8841  -20.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8814  -20.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1633  -21.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1602  -22.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8739  -22.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5921  -22.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5917  -21.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357  -13.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7495  -12.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0413  -12.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3177  -12.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3075  -13.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3751  -13.6543    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  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
 25 26  1  0
 21 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 26 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 26  1  0
M  CHG  4   1  -1   6   1  21   1  39  -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: 531.75

Molecular Weight (Monoisotopic): 531.2116

AlogP: 4.69

#Rotatable Bonds: 12

Polar Surface Area: 47.70

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -1.70

CX LogD: -1.70

Aromatic Rings: 5

Heavy Atoms: 37

QED Weighted: 0.17

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