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

ID: ALA2333420

PubChem CID: 71584201

Max Phase: Preclinical

Molecular Formula: C9H7F4NO4S2

Molecular Weight: 333.28

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H7F4NO4S2/c10-4-6(12)9(20(14,17)18)7(13)5(11)8(4)19-2-1-3(15)16/h1-2H2,(H,15,16)(H2,14,17,18)

Standard InChI Key:  XFZIOQQKZKUFEN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
    7.4812   -8.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4801   -9.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1881   -9.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8978   -9.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8950   -8.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1864   -8.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1839   -7.3709    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8904   -6.9602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3877   -7.5776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7674   -6.6572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6011   -8.1821    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.7734   -8.1886    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.7721   -9.8246    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.6062   -9.8235    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.1879  -10.6427    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.4801  -11.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7725  -10.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0647  -11.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3554  -10.6427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628  -11.8687    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
 18 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2333420

   3-(2,3,5,6-Tetrafluoro-4-sulfamoylphenyl)sulfanylpropanoic 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: 333.28

Molecular Weight (Monoisotopic): 332.9753

AlogP: 1.46

#Rotatable Bonds: 5

Polar Surface Area: 97.46

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.68

CX Basic pKa: ┄

CX LogP: 1.39

CX LogD: -2.95

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.48

Np Likeness Score: -0.95

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