4-(5-(2,6-Difluoro-3-hydroxybenzoyl)thiophen-2-yl)benzenesulfonamide

ID: ALA4094112

PubChem CID: 122652947

Max Phase: Preclinical

Molecular Formula: C17H11F2NO4S2

Molecular Weight: 395.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(-c2ccc(C(=O)c3c(F)ccc(O)c3F)s2)cc1

Standard InChI:  InChI=1S/C17H11F2NO4S2/c18-11-5-6-12(21)16(19)15(11)17(22)14-8-7-13(25-14)9-1-3-10(4-2-9)26(20,23)24/h1-8,21H,(H2,20,23,24)

Standard InChI Key:  JDOHUDBLGARBIY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    9.5174  -14.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5215  -15.3450    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.2272  -14.9329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5686  -16.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5675  -17.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755  -18.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852  -17.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9824  -16.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2737  -16.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2713  -15.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778  -15.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5624  -15.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7298  -15.6273    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2748  -15.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8641  -14.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0653  -14.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0836  -15.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4175  -15.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2297  -15.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7089  -15.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3701  -14.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5590  -14.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885  -16.5191    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8608  -16.5256    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595  -18.1616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8576  -16.0932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 11  2  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 14 17  1  0
  8 23  1  0
  4 24  1  0
  5 25  1  0
 20  2  1  0
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4094112

   ---

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: 395.41

Molecular Weight (Monoisotopic): 395.0098

AlogP: 3.28

#Rotatable Bonds: 4

Polar Surface Area: 97.46

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.72

CX Basic pKa: ┄

CX LogP: 3.58

CX LogD: 3.41

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: -1.04

References

1. Abdelsamie AS, van Koppen CJ, Bey E, Salah M, Börger C, Siebenbürger L, Laschke MW, Menger MD, Frotscher M..  (2017)  Treatment of estrogen-dependent diseases: Design, synthesis and profiling of a selective 17β-HSD1 inhibitor with sub-nanomolar IC50 for a proof-of-principle study.,  127  [PMID:27852458] [10.1016/j.ejmech.2016.11.004]

2. Abdelsamie AS, Salah M, Siebenbürger L, Hamed MM, Börger C, van Koppen CJ, Frotscher M, Hartmann RW..  (2019)  Development of potential preclinical candidates with promising in vitro ADME profile for the inhibition of type 1 and type 2 17β-Hydroxysteroid dehydrogenases: Design, synthesis, and biological evaluation.,  178  [PMID:31176098] [10.1016/j.ejmech.2019.05.084]

Source

Source(1):

• Scientific Literature