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

ID: ALA4101849

PubChem CID: 122652975

Max Phase: Preclinical

Molecular Formula: C16H9F2NO2S

Molecular Weight: 317.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(-c2cccnc2)s1)c1c(F)ccc(O)c1F

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

Standard InChI Key:  HUXTVRJMHUECGN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   14.6375  -19.3209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4625  -19.3209    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.7193  -18.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0500  -18.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3850  -18.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1517  -19.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3313  -19.9004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4862  -20.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9987  -21.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3326  -22.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1538  -22.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6399  -21.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3034  -20.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1784  -21.3202    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.8465  -22.8286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5005  -18.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1127  -18.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8971  -18.5829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0703  -17.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4531  -17.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6711  -17.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7872  -20.1589    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:

   

   ALA4101849

   ---

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: 4.41

CX LogP: 3.75

CX LogD: 3.59

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.74

Np Likeness Score: -0.94

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