3-methyl-2-((1-(2-oxo-2-(2-(piperidin-1-yl)ethylamino)ethyl)quinolin-4(1H)-ylidene)methyl)benzo[d]thiazol-3-ium bromide

ID: ALA4459668

PubChem CID: 155527457

Max Phase: Preclinical

Molecular Formula: C27H31BrN4OS

Molecular Weight: 459.64

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[n+]1c(/C=C2\C=CN(CC(=O)NCCN3CCCCC3)c3ccccc32)sc2ccccc21.[Br-]

Standard InChI:  InChI=1S/C27H30N4OS.BrH/c1-29-24-11-5-6-12-25(24)33-27(29)19-21-13-17-31(23-10-4-3-9-22(21)23)20-26(32)28-14-18-30-15-7-2-8-16-30;/h3-6,9-13,17,19H,2,7-8,14-16,18,20H2,1H3;1H

Standard InChI Key:  DWEIEBUWFABVRO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   18.4859  -12.4849    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.2582  -13.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2570  -14.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9651  -14.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9633  -13.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6719  -13.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6721  -14.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4551  -14.5821    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.9388  -13.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4547  -13.2502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7560  -13.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1649  -14.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7515  -15.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1568  -16.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9744  -16.0433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9779  -14.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3830  -15.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2003  -15.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6134  -14.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2033  -13.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3874  -13.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3812  -16.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7070  -12.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1983  -16.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6051  -17.4628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6087  -16.0474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4259  -16.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8327  -16.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6499  -16.7603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0498  -17.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8634  -17.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2776  -16.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8721  -16.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0523  -16.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 16  1  0
 13 14  2  0
 14 15  1  0
 15 17  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 15 22  1  0
 10 23  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 34  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
M  CHG  2   1  -1  10   1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 459.64

Molecular Weight (Monoisotopic): 459.2213

AlogP: 4.20

#Rotatable Bonds: 6

Polar Surface Area: 39.46

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.38

CX LogP: 0.00

CX LogD: -1.03

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.56

Np Likeness Score: -1.05

References

1. Wang S, Yang D, Singh M, Joo H, Rangel VM, Tran A, Phan E, Xue L..  (2019)  Thiazole orange - Spermine conjugate: A potent human telomerase inhibitor comparable to BRACO-19.,  175  [PMID:31071547] [10.1016/j.ejmech.2019.04.041]

Source

Source(1):

• Scientific Literature