10-Hydroxy-5-methyl-12(H)-quino[3,4-b][1,4]benzothiazinium chloride

ID: ALA1278152

PubChem CID: 49845319

Max Phase: Preclinical

Molecular Formula: C16H13ClN2OS

Molecular Weight: 281.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[n+]1cc2c(c3ccccc31)Nc1cc(O)ccc1S2.[Cl-]

Standard InChI:  InChI=1S/C16H12N2OS.ClH/c1-18-9-15-16(11-4-2-3-5-13(11)18)17-12-8-10(19)6-7-14(12)20-15;/h2-9,19H,1H3;1H

Standard InChI Key:  ULPVGAMIQJZQOA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    9.1384  -12.6637    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7615  -12.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7603  -12.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4710  -13.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4692  -11.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1805  -12.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1839  -12.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8990  -13.2961    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922  -11.6381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6160  -12.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6170  -12.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3324  -13.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0514  -12.8829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3303  -11.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0467  -12.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7636  -11.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7653  -10.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0443  -10.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3303  -10.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7625  -13.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0463  -11.6521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
 10 14  1  0
 11 12  1  0
 12 13  2  0
 13 15  1  0
  2  3  2  0
 14 15  2  0
  3  4  1  0
 15 16  1  0
  4  7  2  0
 16 17  2  0
  6  9  1  0
 17 18  1  0
  7  8  1  0
 18 19  2  0
 19 14  1  0
  8 11  1  0
 13 20  1  0
 10  9  1  0
  2 21  1  0
 10 11  2  0
M  CHG  2   1  -1  13   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: 281.36

Molecular Weight (Monoisotopic): 281.0743

AlogP: 3.58

#Rotatable Bonds: ┄

Polar Surface Area: 36.14

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.34

CX Basic pKa: ┄

CX LogP: -0.82

CX LogD: -0.82

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.48

Np Likeness Score: 0.29

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