4-Chloro-N-[4-(phenethylsulfamoyl)phenyl]benzenesulfonamide

ID: ALA1797553

Cas Number: 606922-74-1

PubChem CID: 3899814

Max Phase: Preclinical

Molecular Formula: C20H19ClN2O4S2

Molecular Weight: 450.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(NCCc1ccccc1)c1ccc(NS(=O)(=O)c2ccc(Cl)cc2)cc1

Standard InChI:  InChI=1S/C20H19ClN2O4S2/c21-17-6-10-20(11-7-17)29(26,27)23-18-8-12-19(13-9-18)28(24,25)22-15-14-16-4-2-1-3-5-16/h1-13,22-23H,14-15H2

Standard InChI Key:  PQQLODYVGLJYKM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   22.2646  -23.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2634  -24.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9789  -24.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6960  -24.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6931  -23.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9771  -23.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5479  -24.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8332  -24.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1177  -24.6646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4030  -24.2512    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.6875  -24.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8128  -23.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8096  -23.5338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9762  -24.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2612  -24.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2601  -25.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9800  -25.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6919  -25.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5453  -25.9007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8299  -25.4882    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.1207  -25.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2388  -24.8976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0395  -24.6849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4106  -25.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7019  -25.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7047  -26.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4223  -27.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1280  -26.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9919  -27.1446    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
  7  8  1  0
 16 17  1  0
 17 18  2  0
 18 11  1  0
  8  9  1  0
 16 19  1  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
  2  3  1  0
 20 22  2  0
 10 11  1  0
 20 23  2  0
  5  6  2  0
 21 24  2  0
 10 12  2  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 10 13  2  0
 26 27  1  0
  1  2  2  0
 27 28  2  0
 28 21  1  0
 11 14  2  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1797553

   4-Chloro-N-(4-(N-phenethylsulfamoyl)phenyl)benzenesulfonamide

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: 450.97

Molecular Weight (Monoisotopic): 450.0475

AlogP: 3.66

#Rotatable Bonds: 8

Polar Surface Area: 92.34

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.51

CX Basic pKa: ┄

CX LogP: 3.91

CX LogD: 3.69

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: -1.41

References

1. Bissinger EM, Heinke R, Spannhoff A, Eberlin A, Metzger E, Cura V, Hassenboehler P, Cavarelli J, Schüle R, Bedford MT, Sippl W, Jung M..  (2011)  Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1.,  19  (12): [PMID:21440447] [10.1016/j.bmc.2011.02.032]

Source

Source(1):

• Scientific Literature