5-(2-Methoxyethyl)-3-(3-(1-(5-(5-(2-methoxyethyl)-4-methylthiazol-3-ium-3-yl)pentyl)-1H-1,2,3-triazol-4-yl)propyl)-4-methylthiazol-3-ium Chloride

ID: ALA2314647

PubChem CID: 71520842

Max Phase: Preclinical

Molecular Formula: C24H39Cl2N5O2S2

Molecular Weight: 493.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCc1sc[n+](CCCCCn2cc(CCC[n+]3csc(CCOC)c3C)nn2)c1C.[Cl-].[Cl-]

Standard InChI:  InChI=1S/C24H39N5O2S2.2ClH/c1-20-23(10-15-30-3)32-18-27(20)12-6-5-7-14-29-17-22(25-26-29)9-8-13-28-19-33-24(21(28)2)11-16-31-4;;/h17-19H,5-16H2,1-4H3;2*1H/q+2;;/p-2

Standard InChI Key:  OADLILYFBCPUST-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 35 35  0  0  0  0  0  0  0  0999 V2000
   14.1163  -26.6533    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6456  -25.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4706  -25.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7278  -25.1481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0581  -24.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3931  -25.1484    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9548  -26.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2382  -26.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132  -26.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0058  -27.3725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4760  -24.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1511  -25.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8993  -24.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5744  -25.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5891  -26.2246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3778  -26.4670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8519  -25.7918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3564  -25.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6768  -25.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1007  -26.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808  -27.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9256  -26.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3495  -27.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1745  -27.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6591  -27.8347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4060  -28.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0732  -29.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7408  -28.6169    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.4861  -27.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6215  -28.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0728  -29.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7872  -30.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7868  -31.1644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5011  -31.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0582  -23.7784    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
 10 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 25  2  0
 26 30  1  0
 27 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
M  CHG  4   1  -1   4   1  25   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: 493.74

Molecular Weight (Monoisotopic): 493.2534

AlogP: 3.47

#Rotatable Bonds: 16

Polar Surface Area: 56.93

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.49

CX LogP: -3.64

CX LogD: -3.64

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.23

Np Likeness Score: -0.80

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