2-Benzylsulfonyl-4-bromo-N-(2-hydroxyethyl)-5-sulfamoylbenzamide

ID: ALA4513913

PubChem CID: 126509348

Max Phase: Preclinical

Molecular Formula: C16H17BrN2O6S2

Molecular Weight: 477.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1cc(C(=O)NCCO)c(S(=O)(=O)Cc2ccccc2)cc1Br

Standard InChI:  InChI=1S/C16H17BrN2O6S2/c17-13-9-14(26(22,23)10-11-4-2-1-3-5-11)12(16(21)19-6-7-20)8-15(13)27(18,24)25/h1-5,8-9,20H,6-7,10H2,(H,19,21)(H2,18,24,25)

Standard InChI Key:  PYLVVDNHUGVMGF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   24.9356   -3.8885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5311   -4.5984    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.3481   -4.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5349   -5.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2435   -5.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2464   -6.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5367   -7.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8287   -6.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8298   -5.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5365   -7.8709    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.8287   -8.2793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9458   -8.5798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3544   -7.8709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9497   -5.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6589   -5.8162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9466   -4.5931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8236   -4.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3651   -5.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0744   -5.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7805   -5.3996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1206   -7.0527    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   23.8212   -3.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5264   -2.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5243   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8149   -1.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1061   -2.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1116   -2.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  2  1  0
  5  4  2  0
  6  5  1  0
  7  6  2  0
  8  7  1  0
  9  8  2  0
  4  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  2  0
 10 13  2  0
  5 14  1  0
 14 15  1  0
 14 16  2  0
  2 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
  8 21  1  0
 17 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513913

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 477.36

Molecular Weight (Monoisotopic): 475.9711

AlogP: 0.79

#Rotatable Bonds: 7

Polar Surface Area: 143.63

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.41

CX Basic pKa: ┄

CX LogP: 0.45

CX LogD: 0.41

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: -1.29

References

1. Zakšauskas A, Čapkauskaitė E, Jezepčikas L, Linkuvienė V, Paketurytė V, Smirnov A, Leitans J, Kazaks A, Dvinskis E, Manakova E, Gražulis S, Tars K, Matulis D..  (2020)  Halogenated and di-substituted benzenesulfonamides as selective inhibitors of carbonic anhydrase isoforms.,  185  [PMID:31740053] [10.1016/j.ejmech.2019.111825]

Source

Source(1):

• Scientific Literature