(2,6-Difluoro-3-hydroxyphenyl)(5-(4-hydroxyphenyl)thiophen-2-yl)methanone

ID: ALA4071588

PubChem CID: 137640293

Max Phase: Preclinical

Molecular Formula: C17H10F2O3S

Molecular Weight: 332.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(-c2ccc(O)cc2)s1)c1c(F)ccc(O)c1F

Standard InChI:  InChI=1S/C17H10F2O3S/c18-11-5-6-12(21)16(19)15(11)17(22)14-8-7-13(23-14)9-1-3-10(20)4-2-9/h1-8,20-21H

Standard InChI Key:  HDNHNXBACWULOX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   14.2912  -22.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2900  -23.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9981  -24.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7077  -23.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7049  -22.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9963  -22.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9938  -21.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7003  -21.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2849  -21.1621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4524  -21.4880    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.9974  -20.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5866  -20.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7879  -20.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8062  -20.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1400  -21.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9522  -21.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4314  -21.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0927  -20.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2815  -20.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4111  -22.3798    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.5834  -22.3862    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.5820  -24.0222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2445  -21.2088    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
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  8  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 11 14  1  0
  5 20  1  0
  1 21  1  0
  2 22  1  0
 17 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4071588

   ---

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: 332.33

Molecular Weight (Monoisotopic): 332.0319

AlogP: 4.34

#Rotatable Bonds: 3

Polar Surface Area: 57.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.71

CX Basic pKa: ┄

CX LogP: 4.67

CX LogD: 4.50

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: -0.45

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. Salah M, Abdelsamie AS, Frotscher M..  (2017)  First Dual Inhibitors of Steroid Sulfatase (STS) and 17β-Hydroxysteroid Dehydrogenase Type 1 (17β-HSD1): Designed Multiple Ligands as Novel Potential Therapeutics for Estrogen-Dependent Diseases.,  60  (9): [PMID:28406629] [10.1021/acs.jmedchem.7b00062]

Source

Source(1):

• Scientific Literature