(2,6-Difluoro-3-hydroxy-phenyl)-(5-pyridin-4-yl-thiophen-2-yl)-methanone

ID: ALA4091622

PubChem CID: 122653001

Max Phase: Preclinical

Molecular Formula: C16H9F2NO2S

Molecular Weight: 317.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(-c2ccncc2)s1)c1c(F)ccc(O)c1F

Standard InChI:  InChI=1S/C16H9F2NO2S/c17-10-1-2-11(20)15(18)14(10)16(21)13-4-3-12(22-13)9-5-7-19-8-6-9/h1-8,20H

Standard InChI Key:  BVGMSNSBQLORRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   23.3466   -3.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1717   -3.0210    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.4285   -2.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7592   -1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0941   -2.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8608   -3.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0404   -3.6005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1955   -4.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7079   -5.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0418   -5.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8630   -5.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3492   -5.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0126   -4.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8876   -5.0204    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.5556   -6.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2097   -1.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8220   -2.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6064   -2.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7797   -1.4754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1624   -0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3804   -1.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4965   -3.8591    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
  1  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  9 14  1  0
 10 15  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
  3 16  1  0
 13 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091622

   ---

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: 317.32

Molecular Weight (Monoisotopic): 317.0322

AlogP: 4.02

#Rotatable Bonds: 3

Polar Surface Area: 50.19

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: 4.16

CX LogP: 3.75

CX LogD: 3.59

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.74

Np Likeness Score: -0.82

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