3,3'-(Thiophene-2,5-diylbis(butane-4,1-diyl))bis(5-(2-hydroxyethyl)-4-methylthiazol-3-ium)Chloride

ID: ALA2314634

PubChem CID: 71521377

Max Phase: Preclinical

Molecular Formula: C24H36Cl2N2O2S3

Molecular Weight: 480.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CCO)sc[n+]1CCCCc1ccc(CCCC[n+]2csc(CCO)c2C)s1.[Cl-].[Cl-]

Standard InChI:  InChI=1S/C24H36N2O2S3.2ClH/c1-19-23(11-15-27)29-17-25(19)13-5-3-7-21-9-10-22(31-21)8-4-6-14-26-18-30-24(12-16-28)20(26)2;;/h9-10,17-18,27-28H,3-8,11-16H2,1-2H3;2*1H/q+2;;/p-2

Standard InChI Key:  NGBWYYFZJCFHJC-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 33 33  0  0  0  0  0  0  0  0999 V2000
   15.9581   -7.3124    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.2318   -8.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5704   -8.1781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8945   -8.6528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1403   -9.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9632   -9.4511    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.9498   -8.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9526   -7.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6685   -7.0258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5824   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8027   -8.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4987   -8.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2302   -8.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0720   -8.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3589   -8.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0191   -8.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2997   -9.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1247   -9.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3821   -8.3902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7122   -7.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0481   -8.3901    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.0986   -7.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8110   -8.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8789   -9.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2844  -10.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8648  -11.3162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6087   -9.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5275   -7.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2398   -8.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7052   -8.5841    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.0760   -7.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2476   -7.3233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2621   -7.5624    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
  2  7  1  0
  7  8  1  0
  8  9  1  0
  3 10  1  0
 11 12  1  0
 12 13  1  0
 13  4  1  0
 14 11  1  0
 15 14  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  1  0
 19 22  1  0
 22 23  1  0
 17 24  1  0
 24 25  1  0
 25 26  1  0
 18 27  1  0
 23 28  1  0
 28 29  1  0
 29 16  1  0
 16 30  1  0
 30 15  1  0
 15 31  2  0
 31 32  1  0
 32 16  2  0
M  CHG  4   1  -1   4   1  19   1  33  -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: 480.77

Molecular Weight (Monoisotopic): 480.1928

AlogP: 4.18

#Rotatable Bonds: 14

Polar Surface Area: 48.22

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -2.28

CX LogD: -2.28

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: -0.21

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