3-chloro-N-(2,4-difluoro-3-((3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)phenyl)benzenesulfonamide

ID: ALA4096439

PubChem CID: 137655959

Max Phase: Preclinical

Molecular Formula: C21H13ClF2N4O3S

Molecular Weight: 474.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1n[nH]c2ncc(C#Cc3c(F)ccc(NS(=O)(=O)c4cccc(Cl)c4)c3F)cc12

Standard InChI:  InChI=1S/C21H13ClF2N4O3S/c1-31-21-16-9-12(11-25-20(16)26-27-21)5-6-15-17(23)7-8-18(19(15)24)28-32(29,30)14-4-2-3-13(22)10-14/h2-4,7-11,28H,1H3,(H,25,26,27)

Standard InChI Key:  NEDXWYOBFJNWEA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   23.8237   -4.5789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4154   -3.8665    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.0026   -4.5763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5600   -3.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5588   -4.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2736   -5.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9900   -4.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9872   -3.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2718   -3.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7001   -3.4602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1289   -3.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2693   -2.6413    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.8441   -5.1182    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.8454   -3.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1275   -3.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4129   -2.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4167   -1.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7029   -1.4051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7051   -3.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9907   -2.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9908   -1.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1990   -1.5572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7095   -2.2308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1989   -2.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9439   -3.6889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1369   -3.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8432   -3.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5556   -3.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5530   -2.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8320   -2.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1226   -2.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8260   -1.3931    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10  2  1  0
  2 11  1  0
  9 12  1  0
  5 13  1  0
  4 14  1  0
 14 15  3  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 21  2  0
 20 19  2  0
 19 16  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 20  1  0
 24 25  1  0
 25 26  1  0
 11 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 11  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096439

   ---

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: 474.88

Molecular Weight (Monoisotopic): 474.0365

AlogP: 4.10

#Rotatable Bonds: 4

Polar Surface Area: 96.97

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.38

CX Basic pKa: 0.84

CX LogP: 4.38

CX LogD: 4.34

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -2.00

References

1. Chang Y, Lu X, Shibu MA, Dai YB, Luo J, Zhang Y, Li Y, Zhao P, Zhang Z, Xu Y, Tu ZC, Zhang QW, Yun CH, Huang CY, Ding K..  (2017)  Structure Based Design of N-(3-((1H-Pyrazolo[3,4-b]pyridin-5-yl)ethynyl)benzenesulfonamides as Selective Leucine-Zipper and Sterile-α Motif Kinase (ZAK) Inhibitors.,  60  (13): [PMID:28586211] [10.1021/acs.jmedchem.7b00572]

2. Yang J, Shibu MA, Kong L, Luo J, BadrealamKhan F, Huang Y, Tu ZC, Yun CH, Huang CY, Ding K, Lu X..  (2020)  Design, Synthesis, and Structure-Activity Relationships of 1,2,3-Triazole Benzenesulfonamides as New Selective Leucine-Zipper and Sterile-α Motif Kinase (ZAK) Inhibitors.,  63  (5): [PMID:31244114] [10.1021/acs.jmedchem.9b00664]

Source

Source(1):

• Scientific Literature