[5-(2,4-Difluoro-phenyl)-thiophen-2-yl]-(2,4,5-trifluoro-3-hydroxy-phenyl)-methanone

ID: ALA4092593

PubChem CID: 122652926

Max Phase: Preclinical

Molecular Formula: C17H7F5O2S

Molecular Weight: 370.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(-c2ccc(F)cc2F)s1)c1cc(F)c(F)c(O)c1F

Standard InChI:  InChI=1S/C17H7F5O2S/c18-7-1-2-8(10(19)5-7)12-3-4-13(25-12)16(23)9-6-11(20)15(22)17(24)14(9)21/h1-6,24H

Standard InChI Key:  QVHCDCUIBFYPSB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   14.5278  -10.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450  -10.6937    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.5994   -9.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9364   -9.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2777   -9.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3732   -9.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9796  -10.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7565   -9.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9282   -9.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3167   -8.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5422   -8.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8078  -11.0124    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.7054   -8.9103    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.0466  -11.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2340  -11.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3780  -12.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8951  -12.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2258  -13.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0393  -13.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5208  -12.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1874  -12.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0825  -12.6741    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.7443  -14.1682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3717  -14.3415    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.3337  -13.0131    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3  6  1  0
  7 12  1  0
  9 13  1  0
  1 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 17 22  1  0
 18 23  1  0
 19 24  1  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092593

   ---

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: 370.30

Molecular Weight (Monoisotopic): 370.0087

AlogP: 5.05

#Rotatable Bonds: 3

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.18

CX Basic pKa: ┄

CX LogP: 5.40

CX LogD: 4.23

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.40

Np Likeness Score: -0.89

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. Siebenbuerger L, Hernandez-Olmos V, Abdelsamie AS, Frotscher M, van Koppen CJ, Marchais-Oberwinkler S, Scheuer C, Laschke MW, Menger MD, Boerger C, Hartmann RW..  (2018)  Highly Potent 17β-HSD2 Inhibitors with a Promising Pharmacokinetic Profile for Targeted Osteoporosis Therapy.,  61  (23): [PMID:30480443] [10.1021/acs.jmedchem.8b01373]

Source

Source(1):

• Scientific Literature