3,3'-(([1,1'-Biphenyl]-4,4'-diylbis(oxy))bis(ethane-2,1-diyl))bis(5-(2-methoxyethyl)-4-methyl thiazol-3-ium)Bromide

ID: ALA2314628

PubChem CID: 71520650

Max Phase: Preclinical

Molecular Formula: C30H38Br2N2O4S2

Molecular Weight: 554.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCc1sc[n+](CCOc2ccc(-c3ccc(OCC[n+]4csc(CCOC)c4C)cc3)cc2)c1C.[Br-].[Br-]

Standard InChI:  InChI=1S/C30H38N2O4S2.2BrH/c1-23-29(13-17-33-3)37-21-31(23)15-19-35-27-9-5-25(6-10-27)26-7-11-28(12-8-26)36-20-16-32-22-38-30(24(32)2)14-18-34-4;;/h5-12,21-22H,13-20H2,1-4H3;2*1H/q+2;;/p-2

Standard InChI Key:  CAQMIOGDHOTPIA-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 40 41  0  0  0  0  0  0  0  0999 V2000
    3.9041  -17.0624    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.6733  -22.5807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1296  -23.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5530  -23.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3573  -23.7243    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.4307  -22.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3079  -23.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2291  -24.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4101  -24.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0862  -25.5246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2671  -25.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9613  -21.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8260  -19.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8199  -20.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5325  -20.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2489  -20.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2484  -19.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5353  -18.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9629  -20.5117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6749  -21.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499  -18.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5749  -18.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8323  -18.0068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1624  -17.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984  -18.0068    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5488  -17.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2613  -18.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3291  -19.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346  -20.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3150  -20.9329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7204  -21.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0589  -19.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9777  -17.6048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6902  -18.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6848  -18.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3964  -19.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1138  -18.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1153  -18.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4030  -17.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1499  -22.1540    0.0000 Br  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 18  2  0
 18 13  1  0
 16 19  1  0
 19 12  1  0
 12 20  1  0
 20  2  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  1  0
 23 26  1  0
 26 27  1  0
 21 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 22 32  1  0
 27 33  1  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 34  1  0
 37 13  1  0
M  CHG  4   1  -1   2   1  23   1  40  -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: 554.78

Molecular Weight (Monoisotopic): 554.2262

AlogP: 5.20

#Rotatable Bonds: 15

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: -1.91

CX LogD: -1.91

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.19

Np Likeness Score: -0.25

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