4-((2-(piperazin-1-yl)phenyl)amino)-2a1,5a-dihydro-5H-naphtho[1,8-cd]isothiazol-5-one 1,1-dioxide

ID: ALA5284089

Max Phase: Preclinical

Molecular Formula: C20H20N4O3S

Molecular Weight: 396.47

Names and Identifiers

Canonical SMILES:  O=C1C(Nc2ccccc2N2CCNCC2)=CC2=NS(=O)(=O)C3=CC=CC1C32

Standard InChI:  InChI=1S/C20H20N4O3S/c25-20-13-4-3-7-18-19(13)15(23-28(18,26)27)12-16(20)22-14-5-1-2-6-17(14)24-10-8-21-9-11-24/h1-7,12-13,19,21-22H,8-11H2

Standard InChI Key:  VPDDBBAKQXKGBG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   -2.8592   -0.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592   -0.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421   -1.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7499   -2.0648    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9249   -2.0648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131   -1.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -0.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    0.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    1.2093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -0.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -0.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457    0.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5485   -2.2787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9644   -2.8616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    0.3861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4297   -0.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    0.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566   -0.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463   -1.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4297   -0.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    1.2112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299    1.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299    2.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    2.8616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8592    2.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8592    1.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  6  5  2  0
  3  7  1  0
  7  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 11  9  1  0
 12 11  2  0
 12  6  1  0
 13  1  2  0
  8 13  1  0
  4 14  2  0
  4 15  2  0
 11 16  1  0
 16 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
 23 18  1  0
 23 24  1  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
 28 27  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5284089

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 396.47

Molecular Weight (Monoisotopic): 396.1256

AlogP: 1.45

#Rotatable Bonds: 3

Polar Surface Area: 90.87

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.91

CX Basic pKa: 8.79

CX LogP: 0.76

CX LogD: -0.64

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.80

Np Likeness Score: -0.37

References

1. Dong J, Cheng XD, Zhang WD, Qin JJ..  (2021)  Recent Update on Development of Small-Molecule STAT3 Inhibitors for Cancer Therapy: From Phosphorylation Inhibition to Protein Degradation.,  64  (13.0): [PMID:34170703] [10.1021/acs.jmedchem.1c00629]

Source

Source(1):

• Scientific Literature