5-Buthyl-12(H)-quino[3,4-b][1,4]benzothiazinium bromide

ID: ALA1276900

PubChem CID: 49845488

Max Phase: Preclinical

Molecular Formula: C19H19BrN2S

Molecular Weight: 307.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[n+]1cc2c(c3ccccc31)Nc1ccccc1S2.[Br-]

Standard InChI:  InChI=1S/C19H18N2S.BrH/c1-2-3-12-21-13-18-19(14-8-4-6-10-16(14)21)20-15-9-5-7-11-17(15)22-18;/h4-11,13H,2-3,12H2,1H3;1H

Standard InChI Key:  QJQYZKWGEMSGAW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    3.3333   -1.1833    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -0.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109   -1.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021   -0.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909   -0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874   -1.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4724   -2.1282    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4793   -0.4704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2445   -0.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2456   -1.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9609   -2.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6797   -1.7150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9588   -0.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6751   -0.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919   -0.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3937    0.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6726    0.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587    0.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909   -2.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037   -1.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8198   -2.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5326   -1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9003   -2.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  5  6  1  0
  9 13  1  0
 10 11  1  0
 11 12  2  0
 12 14  1  0
  2  3  2  0
 13 14  2  0
  3 23  1  0
 14 15  1  0
 23  6  2  0
 15 16  2  0
  5  8  1  0
 16 17  1  0
  6  7  1  0
 17 18  2  0
 18 13  1  0
  7 10  1  0
 12 19  1  0
  9  8  1  0
 19 20  1  0
  9 10  2  0
 20 21  1  0
 21 22  1  0
  5  4  2  0
M  CHG  2   1  -1  12   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: 307.44

Molecular Weight (Monoisotopic): 307.1263

AlogP: 5.14

#Rotatable Bonds: 3

Polar Surface Area: 15.91

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.81

CX LogD: 0.81

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.53

Np Likeness Score: -0.24

References

1. Zięba A, Sochanik A, Szurko A, Rams M, Mrozek A, Cmoch P..  (2010)  Synthesis and in vitro antiproliferative activity of 5-alkyl-12(H)-quino[3,4-b] [1,4]benzothiazinium salts.,  45  (11): [PMID:20813435] [10.1016/j.ejmech.2010.07.035]

Source

Source(1):

• Scientific Literature