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

ID: ALA4072426

PubChem CID: 137639781

Max Phase: Preclinical

Molecular Formula: C18H12F2O3S

Molecular Weight: 346.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2ccc(C(=O)c3c(F)ccc(O)c3F)s2)cc1

Standard InChI:  InChI=1S/C18H12F2O3S/c1-23-11-4-2-10(3-5-11)14-8-9-15(24-14)18(22)16-12(19)6-7-13(21)17(16)20/h2-9,21H,1H3

Standard InChI Key:  WNPXUBYCMRHXGU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   14.3820  -16.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3808  -17.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0889  -18.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7985  -17.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7957  -16.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0871  -16.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0846  -15.6873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7911  -15.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3757  -15.2808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5432  -15.6067    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.0882  -14.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6774  -14.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8787  -14.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8970  -15.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2308  -15.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0430  -15.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5222  -15.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1835  -14.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3723  -14.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5019  -16.4985    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.6742  -16.5049    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.6728  -18.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3353  -15.3275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6709  -16.0726    0.0000 C   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
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4072426

   ---

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: 346.35

Molecular Weight (Monoisotopic): 346.0475

AlogP: 4.64

#Rotatable Bonds: 4

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.72

CX Basic pKa: ┄

CX LogP: 4.81

CX LogD: 4.65

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.70

Np Likeness Score: -0.63

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]

Source

Source(1):

• Scientific Literature