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

ID: ALA1276988

PubChem CID: 49845490

Max Phase: Preclinical

Molecular Formula: C25H31BrN2S

Molecular Weight: 391.60

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H30N2S.BrH/c1-2-3-4-5-6-7-8-13-18-27-19-24-25(20-14-9-11-16-22(20)27)26-21-15-10-12-17-23(21)28-24;/h9-12,14-17,19H,2-8,13,18H2,1H3;1H

Standard InChI Key:  OEMJQHMUQXSKII-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   12.2917   -1.1792    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.3486   -0.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3474   -1.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0563   -0.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7675   -0.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7709   -1.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4859   -2.1240    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.4791   -0.4662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2029   -0.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2039   -1.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9192   -2.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6380   -1.7108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9171   -0.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6334   -0.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3503   -0.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3520    0.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6310    0.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9171    0.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3492   -2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0620   -1.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7781   -2.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4910   -1.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2071   -2.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9199   -1.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6360   -2.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3488   -1.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0649   -2.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7778   -1.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0581   -2.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
 13 14  2  0
  3 29  1  0
 14 15  1  0
 29  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
 22 23  1  0
  4  2  1  0
 23 24  1  0
  5  6  1  0
 24 25  1  0
  9 13  1  0
 25 26  1  0
 10 11  1  0
 26 27  1  0
 11 12  2  0
 27 28  1  0
 12 14  1  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: 391.60

Molecular Weight (Monoisotopic): 391.2202

AlogP: 7.48

#Rotatable Bonds: 9

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: 3.48

CX LogD: 3.48

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.24

Np Likeness Score: -0.14

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