3,3'-(((Methylenebis(4,4'-phenylene))bis(oxy))bis(ethane-2,1-diyl))bis(5-(2-methoxyethyl)-4-methylthiazol-3-ium)Chloride

ID: ALA2314626

PubChem CID: 71520840

Max Phase: Preclinical

Molecular Formula: C31H40Cl2N2O4S2

Molecular Weight: 568.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCc1sc[n+](CCOc2ccc(Cc3ccc(OCC[n+]4csc(CCOC)c4C)cc3)cc2)c1C.[Cl-].[Cl-]

Standard InChI:  InChI=1S/C31H40N2O4S2.2ClH/c1-24-30(13-17-34-3)38-22-32(24)15-19-36-28-9-5-26(6-10-28)21-27-7-11-29(12-8-27)37-20-16-33-23-39-31(25(33)2)14-18-35-4;;/h5-12,22-23H,13-21H2,1-4H3;2*1H/q+2;;/p-2

Standard InChI Key:  JHMVGMPHXDMMJY-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 41 42  0  0  0  0  0  0  0  0999 V2000
    3.0000  -12.4042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.7602  -13.5406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0240  -14.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8489  -14.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0926  -13.5214    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.4182  -13.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5478  -14.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3434  -14.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0187  -15.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5132  -16.3888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1885  -17.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3313  -13.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750  -14.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000  -14.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7574  -13.4944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875  -13.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4234  -13.4944    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4739  -13.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1863  -13.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542  -14.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596  -15.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400  -16.4205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455  -17.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839  -14.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9028  -13.0924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6153  -13.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6098  -14.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3214  -14.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0389  -14.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0403  -13.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3281  -13.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7519  -14.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4679  -14.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1793  -14.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8948  -14.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8982  -13.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1802  -13.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4677  -13.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6136  -13.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0469  -13.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2709  -12.3417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  2  2  0
  3  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
 15 18  1  0
 18 19  1  0
 13 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 14 24  1  0
 19 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 29 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 33  1  0
 36 39  1  0
 39 12  1  0
 12 40  1  0
 40  2  1  0
M  CHG  4   1  -1   2   1  15   1  41  -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: 568.81

Molecular Weight (Monoisotopic): 568.2419

AlogP: 5.13

#Rotatable Bonds: 16

Polar Surface Area: 44.68

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -1.47

CX LogD: -1.47

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.18

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