6-{[4-(Aminosulfonyl)-2,3,5,6-tetrafluorophenyl]-amino}hexanoic acid

ID: ALA2333814

PubChem CID: 71584202

Max Phase: Preclinical

Molecular Formula: C12H14F4N2O4S

Molecular Weight: 358.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H14F4N2O4S/c13-7-9(15)12(23(17,21)22)10(16)8(14)11(7)18-5-3-1-2-4-6(19)20/h18H,1-5H2,(H,19,20)(H2,17,21,22)

Standard InChI Key:  UHUKZEBQYYRWMG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   13.1438   -8.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1427   -9.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8507   -9.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5604   -9.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5575   -8.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8489   -8.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8465   -7.5236    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.5530   -7.1129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0503   -7.7303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4300   -6.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2637   -8.3348    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.4360   -8.3413    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.4346   -9.9773    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.2687   -9.9762    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.8505  -10.7954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1427  -11.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4351  -10.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7273  -11.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0197  -10.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3119  -11.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6043  -10.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8964  -11.2028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6045   -9.9771    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
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2333814

   6-(2,3,5,6-Tetrafluoro-4-sulfamoylanilino)hexanoic acid

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: 358.31

Molecular Weight (Monoisotopic): 358.0610

AlogP: 1.95

#Rotatable Bonds: 8

Polar Surface Area: 109.49

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.32

CX Basic pKa: 0.50

CX LogP: 1.52

CX LogD: -2.57

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.37

Np Likeness Score: -0.61

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]

Source

Source(1):

• Scientific Literature