(5-(3-Chloro-4-hydroxy-phenyl)-thiophen-2-yl)-(2,6-difluoro-3-hydroxy-phenyl)-methanone

ID: ALA4063839

PubChem CID: 122653002

Max Phase: Preclinical

Molecular Formula: C17H9ClF2O3S

Molecular Weight: 366.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(-c2ccc(O)c(Cl)c2)s1)c1c(F)ccc(O)c1F

Standard InChI:  InChI=1S/C17H9ClF2O3S/c18-9-7-8(1-3-11(9)21)13-5-6-14(24-13)17(23)15-10(19)2-4-12(22)16(15)20/h1-7,21-22H

Standard InChI Key:  MHGINHFUACJCCL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   24.1924  -16.4470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1913  -17.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8993  -17.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6090  -17.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6061  -16.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8975  -16.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8951  -15.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6016  -14.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1861  -14.8144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3536  -15.1403    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.8986  -14.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4879  -13.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6891  -13.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7074  -14.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0412  -15.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8534  -15.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3326  -14.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9939  -14.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1827  -13.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3123  -16.0321    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.4846  -16.0385    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.4832  -17.6745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1877  -16.1879    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.1457  -14.8611    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
 16 23  1  0
 17 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4063839

   ---

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: 366.77

Molecular Weight (Monoisotopic): 365.9929

AlogP: 4.99

#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: 7.31

CX Basic pKa: ┄

CX LogP: 5.27

CX LogD: 4.86

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.64

Np Likeness Score: -0.80

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