2,3,5,6-Tetrafluoro-4-[(2-hydroxyethyl)sulfonyl]benzenesulfonamide

ID: ALA2333417

PubChem CID: 71299337

Max Phase: Preclinical

Molecular Formula: C8H7F4NO5S2

Molecular Weight: 337.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1c(F)c(F)c(S(=O)(=O)CCO)c(F)c1F

Standard InChI:  InChI=1S/C8H7F4NO5S2/c9-3-5(11)8(20(13,17)18)6(12)4(10)7(3)19(15,16)2-1-14/h14H,1-2H2,(H2,13,17,18)

Standard InChI Key:  WZGGLNWNBUCLIP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   29.7600   -1.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7589   -2.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4669   -3.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1766   -2.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1738   -1.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4651   -1.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4627   -0.7715    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.1692   -0.3608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6665   -0.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0462   -0.0578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8799   -1.5827    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.0522   -1.5891    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.0509   -3.2251    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.8849   -3.2241    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.4667   -4.0432    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.7589   -4.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7587   -5.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0509   -5.6773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2514   -3.8259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0409   -4.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  7 10  2  0
  5 11  1  0
  1 12  1  0
  2 13  1  0
  4 14  1  0
  3 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 15 19  2  0
 15 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2333417

   2,3,5,6-Tetrafluoro-4-[(2-Hydroxyethyl)sulfonyl]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: 337.27

Molecular Weight (Monoisotopic): 336.9702

AlogP: -0.34

#Rotatable Bonds: 4

Polar Surface Area: 114.53

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.48

CX Basic pKa: ┄

CX LogP: -0.55

CX LogD: -1.45

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.58

Np Likeness Score: -0.80

References

1. Dudutienė V, Zubrienė A, Smirnov A, Gylytė J, Timm D, Manakova E, Gražulis S, Matulis D..  (2013)  4-Substituted-2,3,5,6-tetrafluorobenzenesulfonamides as inhibitors of carbonic anhydrases I, II, VII, XII, and XIII.,  21  (7): [PMID:23394791] [10.1016/j.bmc.2013.01.008]

2. Dudutienė V, Matulienė J, Smirnov A, Timm DD, Zubrienė A, Baranauskienė L, Morkūnaite V, Smirnovienė J, Michailovienė V, Juozapaitienė V, Mickevičiūtė A, Kazokaitė J, Bakšytė S, Kasiliauskaitė A, Jachno J, Revuckienė J, Kišonaitė M, Pilipuitytė V, Ivanauskaitė E, Milinavičiūtė G, Smirnovas V, Petrikaitė V, Kairys V, Petrauskas V, Norvaišas P, Lingė D, Gibieža P, Capkauskaitė E, Zakšauskas A, Kazlauskas E, Manakova E, Gražulis S, Ladbury JE, Matulis D..  (2014)  Discovery and characterization of novel selective inhibitors of carbonic anhydrase IX.,  57  (22): [PMID:25358084] [10.1021/jm501003k]

Source

Source(1):

• Scientific Literature