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

ID: ALA4099360

PubChem CID: 122652994

Max Phase: Preclinical

Molecular Formula: C17H9ClF2O2S

Molecular Weight: 350.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(-c2cccc(Cl)c2)s1)c1c(F)ccc(O)c1F

Standard InChI:  InChI=1S/C17H9ClF2O2S/c18-10-3-1-2-9(8-10)13-6-7-14(23-13)17(22)15-11(19)4-5-12(21)16(15)20/h1-8,21H

Standard InChI Key:  GZSYUTDYBGNVIQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   24.3699   -4.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3687   -5.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0768   -5.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7864   -5.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7836   -4.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0750   -3.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0725   -3.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7790   -2.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3636   -2.6350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5311   -2.9608    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.0761   -2.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6653   -1.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8666   -1.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8849   -2.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2187   -3.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0309   -3.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5101   -2.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1714   -1.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3602   -1.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4898   -3.8527    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.6621   -3.8591    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.6607   -5.4951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3651   -4.0085    0.0000 Cl  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
M  END

Alternative Forms

1. Parent:

   

   ALA4099360

   ---

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: 350.77

Molecular Weight (Monoisotopic): 349.9980

AlogP: 5.28

#Rotatable Bonds: 3

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.72

CX Basic pKa: ┄

CX LogP: 5.58

CX LogD: 5.41

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.65

Np Likeness Score: -1.04

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