N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)naphthalene-2-sulfonamide

ID: ALA595786

PubChem CID: 3800302

Max Phase: Preclinical

Molecular Formula: C19H16N4O4S3

Molecular Weight: 460.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nnc(NS(=O)(=O)c2ccc(NS(=O)(=O)c3ccc4ccccc4c3)cc2)s1

Standard InChI:  InChI=1S/C19H16N4O4S3/c1-13-20-21-19(28-13)23-29(24,25)17-10-7-16(8-11-17)22-30(26,27)18-9-6-14-4-2-3-5-15(14)12-18/h2-12,22H,1H3,(H,21,23)

Standard InChI Key:  YHFXJWRRQDJXOA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   12.4951   -8.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0070   -7.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7570   -6.4834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7534   -5.3687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4020   -5.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1007   -5.2419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8020   -5.9941    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8041   -7.1941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8422   -6.5925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5007   -5.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2032   -5.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9026   -5.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995   -3.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -3.0012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.5004    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6378   -0.9001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6383   -2.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1971   -2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4977   -3.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5398   -7.4705    0.0000 S   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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  2  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 21  1  0
 26 27  2  0
 27 18  1  0
 13 28  1  0
 28 29  2  0
 29 10  1  0
  5 30  1  0
 30  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA595786

   N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)naphthalene-2-sulfonamide

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: 460.56

Molecular Weight (Monoisotopic): 460.0334

AlogP: 3.60

#Rotatable Bonds: 6

Polar Surface Area: 118.12

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.59

CX Basic pKa: 0.57

CX LogP: 2.52

CX LogD: 1.74

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.45

Np Likeness Score: -1.73

References

1. Du-Cuny L, Song Z, Moses S, Powis G, Mash EA, Meuillet EJ, Zhang S..  (2009)  Computational modeling of novel inhibitors targeting the Akt pleckstrin homology domain.,  17  (19): [PMID:19734051] [10.1016/j.bmc.2009.08.022]

2.  (2016)  Small molecule inhibitors of the pleckstrin homology domain and methods for using same, 

3.  (2017)  Inhibitors of grb2-associated binding protein 1 (gab1) and methods of treating cancer using the same, 

Source

Source(3):

• Scientific Literature
• BindingDB Database
• Patent Bioactivity Data